<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd" xmlns:googleplay="http://www.google.com/schemas/play-podcasts/1.0"><channel><title><![CDATA[Lessons From the Milk Crate]]></title><description><![CDATA[Stories and Encouragement for School Leaders]]></description><link>https://lessonsfromthemilkcrate.substack.com</link><image><url>https://substackcdn.com/image/fetch/$s_!yDqR!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7598b625-a985-4b41-8f3a-1ed7141872d3_1024x1024.png</url><title>Lessons From the Milk Crate</title><link>https://lessonsfromthemilkcrate.substack.com</link></image><generator>Substack</generator><lastBuildDate>Sun, 02 Aug 2026 06:34:47 GMT</lastBuildDate><atom:link href="https://lessonsfromthemilkcrate.substack.com/feed" rel="self" type="application/rss+xml"/><copyright><![CDATA[J. Tanner Curry]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[lessonsfromthemilkcrate@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[lessonsfromthemilkcrate@substack.com]]></itunes:email><itunes:name><![CDATA[Lessons From The Milk Crate]]></itunes:name></itunes:owner><itunes:author><![CDATA[Lessons From The Milk Crate]]></itunes:author><googleplay:owner><![CDATA[lessonsfromthemilkcrate@substack.com]]></googleplay:owner><googleplay:email><![CDATA[lessonsfromthemilkcrate@substack.com]]></googleplay:email><googleplay:author><![CDATA[Lessons From The Milk Crate]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[The Chair Is Not The Prize]]></title><description><![CDATA[Before You Sit In The Chair: Why Leadership Is Bigger Than You Think Part V]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/the-chair-is-not-the-prize</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/the-chair-is-not-the-prize</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sun, 02 Aug 2026 00:28:06 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!eIYS!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Over the past several weeks, we&#8217;ve pulled up a <a href="https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters">milk crate</a> together and reflected on lessons that oftentimes don&#8217;t reveal themselves until you have had a chance to sit in the chair.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!eIYS!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!eIYS!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!eIYS!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!eIYS!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!eIYS!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!eIYS!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg" width="1122" height="1402" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1402,&quot;width&quot;:1122,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:109795,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/209426085?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!eIYS!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!eIYS!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!eIYS!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!eIYS!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4c62090a-2363-40d9-b905-e9e2cb98c131_1122x1402.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><span>We have sat with the truth that </span><strong><a href="https://lessonsfromthemilkcrate.substack.com/p/before-you-sit-in-the-chair-why-leadership">the chair is bigger than it first appears</a></strong><span> and discovered that leadership was never the reward many of us imagined it to be. We wrestled with the quiet reality that </span><strong><a href="https://lessonsfromthemilkcrate.substack.com/p/you-interview-every-day">we interview every day</a></strong><span> long before anyone ever schedules the formal interview. We reflected on how the chair changes our perspective and asks us to carry realities that others simply cannot see from where they stand while recognizing that </span><strong><a href="https://lessonsfromthemilkcrate.substack.com/p/everyone-needs-something-from-the">everyone still needs something from the chair</a></strong><span>. Last week discussed how </span><strong><a href="https://lessonsfromthemilkcrate.substack.com/p/the-hardest-part-isnt-the-kids"><span>schools are almost never held back by children alone</span></a></strong><span>. More often than not, they are held back by the adults entrusted to lead, teach, support, and shape them.</span></p><p>This week feels different. Not because it is more important than the others. But because before we talk about carrying the chair, I think we have to ask ourselves why we wanted it in the first place.</p><p>When I think back to those evenings around the <a href="https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters">milk crate</a>, something stands out to me now that I never fully appreciated then:</p><p>We almost never talked about promotions. We didn&#8217;t spend much time discussing organizational charts or titles. No one sat around dreaming about corner offices or bigger paychecks. Instead, the conversations always found their way back to children. To teachers, schools, communities. To our responsibility.</p><p>Looking back, I realize the milk crate was teaching us something long before we knew we were learning it: Leadership was never presented as a destination. It was always presented as a responsibility.</p><p><em><span>(And if you&#8217;re new here and wondering what the &#8220;milk crate&#8221; is, there&#8217;s a beginning to that story </span><a href="https://lessonsfromthemilkcrate.substack.com/p/lessons-from-the-milk-crate">here</a><span>.)</span></em></p><p>Somewhere along the way, however, I think many of us begin seeing the chair differently. We begin believing that when we finally arrive there, something inside us will finally feel complete.</p><p>That we&#8217;ll finally have influence. That we&#8217;ll finally be successful. That we&#8217;ll finally matter. Maybe that&#8217;s why so many people chase the chair-not because they fully understand it. But because they believe it will give them something they don&#8217;t yet have. (I understand that-I think every ambitious leader has wrestled with that feeling at some point.)</p><p>But before we spend another week talking about the responsibilities of the chair, I think we owe ourselves one honest question.</p><p><strong>Why do I want it?</strong></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!Xsen!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!Xsen!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!Xsen!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!Xsen!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!Xsen!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!Xsen!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/209426085?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!Xsen!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!Xsen!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!Xsen!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!Xsen!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F25f47ee4-ae28-4563-b524-c70dfd4f682b_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>What This Week Understands</h2><p>Before we answer that question, let&#8217;s acknowledge something that deserves more than a passing sentence.</p><p><em>There is absolutely nothing wrong with ambition.</em></p><p>Schools desperately need ambitious people. Children deserve leaders who are hungry to learn, eager to grow, and unwilling to settle for mediocrity. They deserve teachers who aspire to greater influence because they believe they can make a greater difference in the lives of children.</p><p>Healthy ambition has transformed schools. Healthy ambition has rescued struggling cultures. Healthy ambition has inspired entire communities.</p><p>If you aspire to lead because you want to make a greater impact, I hope this series encourages you. We need you. Children need you.</p><p>In fact, one of the great ironies of education is that many of the people most prepared to lead are often the least likely to pursue it. They become so invested in children, so committed to improving their schools, and so busy pouring into others that they rarely stop to think about themselves. Too busy to finish that degree or get the certificate.</p><p>Sometimes those are exactly the people I hope this series convinces to pursue the chair.</p><p>But there is another side of this conversation that we cannot afford to ignore.</p><p>Not every reason for pursuing the chair is worthy of the children who will someday be entrusted to us. That may sound uncomfortable. I hope it does. Because pretending unhealthy ambition doesn&#8217;t exist has never protected a school.</p><p>Some pursue leadership because they have fallen in love with serving others. Others pursue leadership because they have fallen in love with being recognized. Some pursue the chair because they cannot bear watching children receive less than they deserve. Others pursue it because they are tired of answering to someone else. Some pursue leadership because they believe greater responsibility will allow them to invest in more people. Others quietly hope the title will finally give them the respect, influence, or validation they&#8217;ve been searching for.</p><p>Here&#8217;s the difficult part: from the outside, those people may look remarkably similar. They may hold the same certifications. The same degrees. The same experience. They may even interview equally well.</p><p>But over time, the chair has a remarkable way of revealing what we were truly pursuing all along.</p><p>One leader spends years asking, <em>&#8220;How can I better serve these people?&#8221;</em></p><p>Another quietly spends years asking, <em>&#8220;What can this position do for me?&#8221;</em></p><p>That difference doesn&#8217;t always appear on a r&#233;sum&#233;. It doesn&#8217;t always reveal itself in an interview. But eventually, it always reveals itself in the chair.</p><p>Now, before we become too quick to examine everyone else&#8217;s motives, let me offer a word of hope: this isn&#8217;t about judging hearts or condemning other people. It&#8217;s about examining ourselves. (If I&#8217;m honest, my own understanding of success has matured over the years.)</p><p>I don&#8217;t believe any of us begin our journey with perfectly refined motives. Life has a way of refining them. Mentors refine them. Failure refines them. The chair itself refines them. That is the hope. But hope should never silence conviction. Because children deserve leaders whose greatest ambition is not receiving the chair, but faithfully carrying it.</p><p>And that brings us back to the question sitting quietly between us on this old milk crate.</p><p><strong>If the chair never came would I still love the work enough to keep serving?</strong></p><h2>A Lesson Learned</h2><p>One of the greatest misconceptions I carried early in my career was believing that leadership preparation began when I decided I wanted to become a leader. Looking back now, I couldn&#8217;t have been more wrong.</p><p>The work that shaped me never announced itself as preparation. It looked ordinary. It looked like staying when I could have gone home. Helping with work that wasn&#8217;t listed in my job description. Learning systems simply because understanding them might help someone else later. Showing up during the summer because the school needed another set of hands. Building something that would make another teacher&#8217;s work a little easier.</p><p>At the time, none of those moments felt significant. No one called them leadership experiences. No one handed me a certificate. No one suggested they were preparing me for the chair. I simply believed the work needed to be done. Years later, I realized something that has stayed with me ever since: those often unseen moments were never preparing my r&#233;sum&#233;, they were humbling me and preparing my heart.</p><p>And I wonder if we&#8217;ve unintentionally begun preparing aspiring leaders for interviews more than we&#8217;ve prepared them for leadership.</p><p>We celebrate certifications. We applaud degrees. We encourage professional growth. (All of those things matter!) But there is another kind of preparation that no university can award and no interview committee can fully measure.</p><p>It is the quiet habit of serving before anyone asks us to. It is seeing responsibility before receiving authority. It is solving problems before they become assignments. It is caring enough about children that we willingly shoulder work no one required us to carry.</p><div class="callout-block" data-callout="true"><h3 style="text-align: center;"><strong>Because faithful leadership doesn&#8217;t begin the day we receive the title. It begins the day we stop asking what the work owes us and start asking what we owe the work.</strong></h3></div><p>And perhaps that&#8217;s why the finest leaders I&#8217;ve known all seemed to share something in common.</p><p>Long before they ever occupied the chair, they had already fallen in love with the work.</p><h2>Let&#8217;s Sit With That for a Moment</h2><p>If that lesson is true, then I think it changes the way we look at leadership altogether.</p><p>It changes how we prepare. It changes how we define success. It even changes how we recognize future leaders.</p><p>For years, I assumed the people most ready for leadership would be the ones most eager to pursue it. (I don&#8217;t believe that anymore.) </p><p>Some of the finest leaders I&#8217;ve ever known weren&#8217;t chasing the chair at all. They were chasing excellence. They were chasing better instruction. Better relationships. Better systems. Better opportunities for children.</p><p>They simply became so invested in making the place around them better that leadership eventually became another avenue through which they could continue doing what they already loved.</p><p>That is very different from pursuing leadership because we believe leadership itself is the goal.</p><p>I wonder sometimes if we unintentionally send the wrong message to aspiring leaders. We celebrate promotions. We congratulate new titles. We announce new positions. (And we should.) Those are meaningful milestones.</p><p>But perhaps we spend too little time celebrating the teacher who quietly stays after school to help a struggling colleague. The assistant principal who learns budgets simply because understanding them will make the organization stronger. The instructional coach who spends hours investing in teachers without ever asking what recognition they might receive.</p><p>Those people may never make the front page. But I have learned they are often the very people who quietly change the trajectory of an organization.</p><p>Because they are not serving the chair. They are serving <em>the mission</em>.</p><p>There is another reality we have to wrestle with: sometimes we meet people who desperately want leadership. They are eager for the interview. They are excited about the title. They talk often about the next opportunity. Yet they seem strangely uninterested in the ordinary work that prepares someone to carry greater responsibility.</p><p>They don&#8217;t invest in people. They avoid difficult assignments. They do only what is required. They wait to be asked. They wait to be recognized. They wait until someone notices before they begin giving more of themselves.</p><p>That should give all of us pause. Not because those people cannot become wonderful leaders. (They absolutely can.) But because somewhere along the way we have confused wanting the chair with preparing for it. Those are not the same thing.</p><p>Wanting leadership has never prepared anyone to carry it. Faithful stewardship has. That is why I believe one of the greatest indicators of future leadership is not what someone says they hope to become. It is what they faithfully choose to do while no one is promising them anything in return.</p><p>That is where the heart is revealed. And perhaps that is also why the chair has a way of exposing us.</p><p>If we loved people before the chair, we usually love them even more after receiving it. If we loved recognition before the chair, the chair often gives our ego a larger audience. If we loved learning before the chair, the chair usually deepens our curiosity. If we loved serving before the chair, the chair simply expands the number of lives we are able to influence.</p><p>The chair magnifies. It does not manufacture. So maybe the better question has never been, <em>&#8220;Do I want to become a leader?&#8221;</em></p><p>Maybe the better question is,</p><p><strong>&#8220;What is my life already revealing about the kind of leader I am becoming?&#8221;</strong></p><h2>The Responsibility We Share</h2><p>If that question is worth asking, then it carries responsibility for every one of us.</p><p>For those of us <strong>already sitting in the chair</strong>, we have to be careful about the kind of leadership we are modeling.</p><p>Because people are always watching what we celebrate.</p><ul><li><p>If we celebrate titles more than service, people will chase titles. </p></li><li><p>If we celebrate visibility more than faithfulness, people will chase recognition.</p></li><li><p>If we elevate people simply because they are ambitious, without asking whether they have first demonstrated a heart for stewardship, then we should not be surprised when others conclude that leadership is a destination instead of a calling.</p></li></ul><p>Perhaps one of our greatest responsibilities is helping aspiring leaders fall in love with the work before they ever fall in love with the chair.</p><ul><li><p>Invite them into the difficult conversations.</p></li><li><p>Teach them the unseen work.</p></li><li><p>Explain the burden behind the decisions.</p></li><li><p>Help them understand that leadership is not escaping responsibility-it is multiplying it.</p></li></ul><p>But there is responsibility for those <strong>standing beside the chair as well</strong>:</p><p>If you aspire to lead one day, don&#8217;t wait for the title to begin becoming the leader your future school will need.</p><ul><li><p>Don&#8217;t wait until someone asks you to invest in another teacher.</p></li><li><p>Don&#8217;t wait until someone notices before you volunteer.</p></li><li><p>Don&#8217;t wait for an interview before you become a student of the work.</p></li><li><p>Don&#8217;t wait for authority before you begin carrying responsibility.</p></li></ul><p>Because leadership has never been reserved for people who held titles. Leadership has always belonged to people who willingly accepted responsibility long before anyone required it of them.</p><ul><li><p>And if no one ever notices, keep serving.</p></li><li><p>If no promotion comes this year, keep serving.</p></li><li><p>If another opportunity passes you by, keep serving.</p></li></ul><p>Not because serving guarantees the chair. (It doesn&#8217;t.)</p><p>Serve because children are still worthy of your very best, whether your name is on the office door or not.</p><p>That is the kind of ambition I hope never dies.</p><h2>The Heart of the Lesson</h2><p>Somewhere over the years, my definition of success quietly changed.</p><p>I used to think success meant reaching the chair and doing something while seated in it. Today, I believe success is becoming the kind of person worthy of carrying it.</p><p>Those are not the same pursuit.</p><p>One is centered on a position. The other is centered on a person. One asks whether I&#8217;ve arrived. The other asks whether I&#8217;m still growing. One measures what I have achieved. The other measures who I am becoming.</p><div class="callout-block" data-callout="true"><h3 style="text-align: center;"><strong>The longer I sit in the chair, the more convinced I become that the chair itself was never the prize. The people always were.</strong></h3></div><p>The teachers who need someone to believe in them. The first-year educator wondering if they belong. The veteran teacher who needs to be reminded that their work still matters. The child who walks into school every morning carrying burdens no report card will ever measure. The family looking for hope. The community trusting us with what matters most.</p><p><em><strong>That has always been the prize.</strong></em></p><p>The chair simply gives us another opportunity to serve them. Perhaps that&#8217;s why I no longer spend much time wondering about the next chair. Not because I lack ambition. But because my ambition has changed:</p><p>I don&#8217;t wake up asking what opportunity comes next. I wake up asking what opportunity has already been placed in front of me. <em>That shift has brought more peace than any promotion ever could.</em></p><p>Because promotions are temporary. Titles are temporary. Recognition is temporary. Even the chair is temporary-every one of us is simply borrowing it for a season.</p><p>One day another leader will sit where we once sat. Another name will be on the office door. Another vision will be carried forward.</p><p>That realization isn&#8217;t discouraging. I actually find it freeing. Because it reminds me that <strong>the chair never belonged to me-I belonged to the mission</strong>. And missions are always bigger than the people temporarily entrusted to carry them.</p><p>Maybe that&#8217;s the lesson the milk crate was quietly teaching all those years-no one around that crate ever acted like they had arrived. The more they learned, the more they realized there was still to learn. The greater their influence became, the more deeply they invested in someone else&#8217;s future. The higher they climbed, the lower they stooped to serve.</p><p>That is the paradox of faithful leadership. The chair may elevate our responsibility. It should never elevate our ego. Because the moment the chair becomes about us, it stops being about the children. And once leadership stops being about children, it has already begun drifting from its purpose.</p><p>So perhaps before we ever ask whether we&#8217;re ready for the chair, we should ask a different question.</p><p><strong>If no one ever offered me the chair, would I still be doing everything within my power to make this school, these children, and these people better than I found them?</strong></p><p>Because I have become convinced of this:</p><p><strong>The chair is not the prize.</strong></p><p><strong>The opportunity to leave people better than we found them is.</strong></p><h2>The Commission</h2><p>Whether you are already sitting in the chair or quietly hoping one day you will, I hope this week&#8217;s reflection leaves you with more than inspiration.</p><p>I hope it leaves you with examination.</p><p>If you are an aspiring leader, don&#8217;t spend the next year asking how to earn the chair. Spend it becoming the kind of person the chair cannot change. Love the work before you love the title. Invest in people before anyone gives you authority over them. Carry responsibility before someone places it in your job description. Prepare your heart with the same urgency that you prepare your r&#233;sum&#233;. Because children deserve leaders whose character arrived before their title did.</p><p>And if you are already sitting in the chair, remember what first made you worthy of it. Don&#8217;t allow busyness to replace curiosity. Don&#8217;t allow authority to replace humility. Don&#8217;t allow responsibility to replace relationships. Don&#8217;t become so consumed with carrying the chair that you forget why you wanted to carry it in the first place. Never stop investing in people. Never stop becoming a student. Never stop remembering that the spotlight was never yours to keep. It was only yours to redirect.</p><p>One day someone else will inherit the chair you&#8217;re sitting in today. When they do, may they inherit more than your office. May they inherit stronger systems. Healthier culture. More confident teachers. Children who believe in themselves. A community that trusts its school.</p><p>And perhaps most importantly, may they inherit a leader who loved the work so deeply that the chair simply became another place from which to serve.</p><p>Because in the end, that is all the chair was ever meant to be.</p><h1>Reflection for the Week</h1><p>As we sit with this week&#8217;s reflection, let&#8217;s spend less time thinking about the chair and more time thinking about our hearts.</p><p>This week, let&#8217;s marinate on these questions:</p><ul><li><p><strong>Why do I truly aspire to lead?</strong> If no title, recognition, or promotion ever came, would I still find joy in the work itself?</p></li><li><p><strong>What am I doing today that demonstrates I&#8217;m already preparing for tomorrow&#8217;s responsibility?</strong> Am I waiting for permission to lead, or am I faithfully serving where I have already been planted?</p></li><li><p><strong>What does success look like in this season of my life?</strong> Am I measuring my progress by comparison to others, or by the growth of the people entrusted to my care?</p></li><li><p><strong>If someone observed my daily habits, would they conclude that I love the work or that I love the position?</strong></p></li><li><p><strong>When my season in this chair eventually comes to an end, what will remain because I was here?</strong></p></li></ul><p>These aren&#8217;t questions to answer quickly. They&#8217;re questions to carry with us.</p><p>Sometimes the most important answers aren&#8217;t found in a single Saturday morning. They&#8217;re discovered by faithfully living through many Monday mornings afterward.</p><h2><strong>Join Us Weekly</strong></h2><p>Click &#8216;subscribe now&#8217; below to join us weekly for these free reflections.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h1>Recognition</h1><p>As I reflect on this week&#8217;s lesson, I find myself grateful for the people who unknowingly shaped my understanding of leadership long before I ever occupied the chair.</p><p>I think of Doc, who never allowed the spotlight to remain on herself for very long. She had a remarkable way of redirecting every success back toward children, teachers, and the work that still remained. Looking back, I realize she wasn&#8217;t simply teaching us how to lead. She was shielding us from what leadership was never supposed to become.</p><p>I think of the colleagues, teachers, custodians, office staff, cafeteria workers, bus drivers, and students who have each, in their own way, reminded me that leadership has very little to do with titles and everything to do with people.</p><p>Most of all, I think of my family.</p><p>They have walked beside every chair I&#8217;ve ever occupied.</p><p>They have celebrated the victories, carried the disappointments, sacrificed evenings, endured long seasons, and continually reminded me that while leadership may be my calling, it must never become my identity.</p><p>And then I find myself thinking about that old milk crate one more time. It never promised anyone a chair. It simply invited ordinary people to sit long enough to learn what kind of person they ought to become before one was ever offered. Maybe that&#8217;s why I still find myself returning there in my mind. Because long before I learned how to carry the chair, I learned to love the work.</p><p>And perhaps that&#8217;s the lesson I&#8217;ve been trying to share all along: The chair is never the prize. The privilege of faithfully investing in people always has been.</p><p><strong>Before we leave the milk crate this week</strong>, I want to leave you with one final thought.</p><p>The chair will never give you what your heart was never meant to find there. It cannot give you purpose. It cannot give you peace. It cannot give you identity.</p><p>Those things must already be taking root long before someone ever hands you the keys to an office. The chair simply reveals whether we came to serve people or whether we came hoping people would serve us.</p><p>That is why the chair is bigger than we think. It doesn&#8217;t merely increase our influence. It magnifies our heart.</p><p>Pull up a milk crate with us again next Saturday as we continue our journey through <strong>Before You Sit in the Chair: Why Leadership Is Bigger Than You Think. </strong>Next week, we&#8217;ll reflect on another truth that aspiring leaders rarely hear until they&#8217;re already carrying the responsibility themselves.</p><p>Until then, don&#8217;t spend this week asking whether you&#8217;re ready for the chair. Spend this week asking a more difficult question.</p><p><strong>If no one ever offered me the chair, would I still be doing everything within my power to make this school, these children, and these people better than I found them?</strong></p><p>Because the leaders most worthy of carrying the chair are rarely the ones chasing it. More often than not, they are the ones who became so captivated by the work that they forgot to chase the chair at all.</p><p><strong>And that matters more than we know.</strong></p><p></p>]]></content:encoded></item><item><title><![CDATA[The Hardest Part Isn't the Kids]]></title><description><![CDATA[Before You Sit In The Chair: Why Leadership Is Bigger Than You Think Part IV]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/the-hardest-part-isnt-the-kids</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/the-hardest-part-isnt-the-kids</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 25 Jul 2026 14:03:11 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!rvat!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>There was something about the <a href="https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters">milk crate</a> that I didn&#8217;t fully appreciate until years later.</p><p>It wasn&#8217;t simply where we ended the day. It was where I quietly watched experienced leaders carry people.</p><p>Not programs. Not schedules. Not budgets. Just people.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!rvat!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!rvat!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!rvat!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!rvat!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!rvat!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!rvat!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg" width="1122" height="1402" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1402,&quot;width&quot;:1122,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:109795,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/208439623?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!rvat!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!rvat!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!rvat!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!rvat!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2588e788-779d-4bce-a7c8-be8a0833040c_1122x1402.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Around that old plastic crate, conversations rarely stayed on lesson plans or test scores for very long. Before long, they always found their way back to people.</p><p>A teacher who was struggling. A parent who was hurting. A student who needed another chance. A staff member who had reached a crossroads. A difficult conversation no one was looking forward to having the next morning.</p><p>At the time, I assumed those conversations were simply part of leadership. Now I understand they were leadership. <strong>Because leadership has never been primarily about managing buildings. It has always been about stewarding people.</strong></p><p>Over the past several weeks, we have slowly pulled another milk crate into the circle together. We have <span>sat with the truth that </span><strong><a href="https://lessonsfromthemilkcrate.substack.com/p/before-you-sit-in-the-chair-why-leadership">the chair is bigger than it first appears</a></strong> and discovered that leadership was never the reward many of us imagined it to be. We wrestled with the quiet reality that <strong><a href="https://lessonsfromthemilkcrate.substack.com/p/you-interview-every-day">we interview every day</a></strong> long before anyone ever schedules the formal interview. Last week, we reflected on how the chair changes our perspective and asks us to carry realities that others simply cannot see from where they stand while recognizing that <strong><a href="https://lessonsfromthemilkcrate.substack.com/p/everyone-needs-something-from-the">everyone still needs something from the chair</a></strong>.</p><p>Each week has revealed another side of the chair. This week may reveal the side that surprised me most.</p><p>Like most educators, I entered this profession because I loved children. Like many aspiring leaders, I assumed leadership would simply give me a greater opportunity to impact them. I could not have been more wrong.</p><p>Because somewhere between standing beside the chair and eventually sitting in it, I discovered a truth that no leadership class ever taught me:</p><p>One of the first surprises waiting in the chair is discovering that:<strong> </strong></p><div class="callout-block" data-callout="true"><p><strong>schools are almost never held back by children alone. More often than not, they are held back by the adults entrusted to lead, teach, support, and shape them.</strong></p></div><p>Before anyone mistakes that for criticism, let me say this as clearly as I can-the day I accepted the chair, I became one of those adults.</p><p>Which means this week&#8217;s reflection is not about <em>them. </em>It is about <em>us.</em></p><p>Because every one of us is shaping culture somewhere.</p><p>The question is not whether we are influencing it. The question is what kind of culture we are helping create.</p><p>And that may be one of the hardest truths we have pulled up a milk crate to discuss yet.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!St6d!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fef399374-558c-478a-84a1-22ed66df9a8c_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!St6d!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fef399374-558c-478a-84a1-22ed66df9a8c_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!St6d!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fef399374-558c-478a-84a1-22ed66df9a8c_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!St6d!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fef399374-558c-478a-84a1-22ed66df9a8c_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!St6d!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fef399374-558c-478a-84a1-22ed66df9a8c_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!St6d!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fef399374-558c-478a-84a1-22ed66df9a8c_1024x1024.jpeg" width="1024" height="1024" 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class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>What This Week Understands</h2><p><em>Before we go any further, this week understands that children can be difficult.</em></p><p>Some carry trauma that changes how they respond to adults. Some arrive without the support systems we wish every child had. Some classrooms are genuinely challenging. Some families are navigating burdens that no school can completely solve. This reflection does not dismiss any of that.</p><p><em>It also understands that educators are carrying extraordinary expectations.</em></p><p>Teachers are asked to be instructors, counselors, interventionists, communicators, mentors, data analysts, and sometimes the most consistent adult in a child&#8217;s life. Support staff often carry responsibilities far beyond their job descriptions and contractual hours. </p><p>School leaders routinely absorb the expectations of teachers, parents, students, district offices, and entire communities. Many people in our schools are doing remarkable work under incredibly difficult circumstances.</p><p><em>This week understands that leadership can fail people.</em></p><p>There are leaders who micromanage instead of mentor. Leaders who correct before they coach. Leaders who avoid difficult conversations until small problems become organizational problems. Leaders who protect comfort more than culture. Leaders who expect growth without first investing in the people they have been entrusted to lead.</p><p>A poor leader can damage an entire organization. That truth deserves to be acknowledged.</p><p><em>This week also understands that not every struggling employee lacks commitment.</em></p><p>Sometimes expectations were unclear. Sometimes training was inadequate. Sometimes support was missing. Sometimes a good employee is simply walking through a difficult season of life.</p><p>Grace matters. Coaching matters. Support matters. Humanity matters.</p><p><em>This week also understands that sometimes there are people who become destructive to an organization.</em></p><p>Not because they made one poor decision. Not because they needed coaching. Not because they disagreed. But because, over time, they repeatedly choose division over unity. Resistance over growth. Excuses over ownership. Self-interest over mission. </p><p>Those people exist. Pretending they do not does not help children. Neither does pretending every difficult person is toxic.</p><p>Good leaders must possess the discernment to know the difference. Because we cannot control another person&#8217;s willingness to grow. We can only control whether we have faithfully invested in them, poured into them, and created every reasonable opportunity for them to succeed.</p><p>That is stewardship.</p><p>But after we acknowledge all of those realities, we still have to sit with one uncomfortable truth: <strong>children do not carry the primary responsibility for the culture of a school. Adults do.</strong></p><p>Adults establish the expectations. Adults model the behaviors. Adults determine what becomes acceptable. Adults decide whether excellence is pursued or merely discussed. Adults shape the environment children experience every single day.</p><p>So this reflection is not about <em>blaming</em> teachers. It is not about <em>defending</em> principals. It is not about <em>pretending</em> children (and their parents) are easy. </p><p>It is about reminding every one of us, teachers, leaders, support staff, parents, and aspiring administrators alike, that the culture children inherit will almost always reflect the adults who created it.</p><p>And if that is true, then perhaps preparing to faithfully invest in adults deserves far more attention than most of us have ever given it.</p><h2>A Lesson Along the Way</h2><p>Before I became a principal, I thought the greatest challenges in schools walked through the front doors every morning carrying backpacks (or were the parents sending them in).</p><p>The longer I have sat in the chair, the more I have realized many of the greatest challenges arrive carrying coffee.</p><p>Not because adults are the problem. Because adults determine whether problems become culture.</p><p>Children do not decide what excellence looks like. Children do not decide whether accountability matters. Children do not decide whether professionalism becomes the expectation. Children do not decide whether collaboration thrives or gossip spreads. <em><strong>Adults do</strong></em>. </p><div class="callout-block" data-callout="true"><p style="text-align: center;"><strong>Children inherit culture. Adults create it.</strong></p></div><p>That realization changed everything I thought I knew about leadership.</p><p>I spent years learning how to teach children. Very little time was spent preparing me to faithfully invest in adults. No graduate class prepared me for the emotional weight of helping someone grow who did not believe they needed to. No leadership textbook explained how difficult it would be to lovingly hold accountable someone I genuinely cared about. No interview committee ever asked me how I would respond when one adult&#8217;s unwillingness to grow began affecting dozens of others.</p><p>Yet that is exactly what the chair asks. Not occasionally. But regularly. And perhaps that is why so many aspiring leaders are surprised by the emotional weight of leadership.</p><p>This work is rarely about choosing between right and wrong. More often, it is choosing how to faithfully steward people who are all at different places in their journey.</p><p>Some are eager to learn. Some are afraid to fail. Some simply need someone willing to believe in them before they believe in themselves. And some, no matter how much you invest in them, no matter how much grace you extend, no matter how many opportunities you create&#8230;choose <em>not to grow</em>.</p><p>That reality doesn&#8217;t make us cynical.</p><p>It makes us responsible.</p><h2>Let&#8217;s Sit With That for a Moment</h2><p>I think one of the greatest misconceptions about leadership is believing our job is simply to hold people accountable. <em>It isn&#8217;t</em>.</p><p>Our responsibility is to pour into people long before accountability becomes necessary.</p><p>That means coaching. Listening. Modeling. Clarifying expectations. Walking alongside someone instead of simply evaluating them from a distance.</p><p>Too often, leaders wait until Friday afternoon to tell someone everything they did wrong during the week.</p><p>Stewardship looks different.</p><p>Stewardship rolls up its sleeves on Monday. It teaches. It models. It checks in. It asks questions. It removes barriers. It invests before it inspects. Because if we expect people to improve, we have a responsibility to help them improve.</p><p>That is one side of the chair. The other side is much heavier.</p><p>Eventually, every leader reaches a moment when investment must be measured honestly.</p><ul><li><p>Has this person grown?</p></li><li><p>Are they trying? </p></li><li><p>Are they receiving support? </p></li><li><p>Are they becoming better? </p></li><li><p>Or are they simply becoming more comfortable remaining the same?</p></li></ul><p>That is a difficult question because good leaders love people.</p><p>We see potential. We remember our own mistakes. We remember the grace someone once extended to us. So we naturally want to give another chance. And another. And another.</p><p>Sometimes that is exactly the right thing to do. Sometimes it is exactly the wrong thing to do. Because grace without growth eventually becomes permission. Not permission for someone to make another mistake. Permission for dysfunction to become culture.</p><p>That is where the chair becomes lonely because there are moments when stewardship requires another conversation. Moments when protecting the mission means confronting what is harming it. Moments when we have done everything reasonably possible to invest in someone, yet they have chosen not to invest in themselves.</p><p>Those are not moments to become angry. Nor are they moments to become passive. They are moments to become faithful.</p><p>I have learned that we cannot control another person&#8217;s willingness to grow. We cannot make someone care. We cannot make someone embrace accountability. We cannot make someone become a team player. We cannot make someone believe in the mission.</p><p>But we can control whether we have been faithful.</p><ul><li><p>Did I invest?</p></li><li><p>Did I coach?</p></li><li><p>Did I communicate clearly?</p></li><li><p>Did I provide support?</p></li><li><p>Did I extend grace?</p></li><li><p>Did I remain consistent?</p></li><li><p>Did I treat that person with dignity, even when the conversation was difficult?</p></li></ul><p>Those are the questions the chair demands us to reflect on.</p><p>Because at the end of the day, stewardship is measured less by whether everyone stayed happy and more by whether we faithfully cared for both the individual and the organization entrusted to us.</p><p>That is a tension no graduate class ever prepared us to carry.</p><h2>The Responsibility We Share</h2><p><strong>If you&#8217;re already sitting in the chair</strong>, this week ought to challenge you before it comforts you.</p><p>The easiest thing a leader can do is identify problems.</p><p>Anyone can point out what isn&#8217;t working. Anyone can criticize instruction. Anyone can notice negativity. Anyone can identify a toxic employee. Anyone can tell us where the dust is.</p><p>The harder work is asking whether we&#8217;ve faithfully invested in the people we expect to improve.</p><ul><li><p>Have we made our expectations clear?</p></li><li><p>Have we modeled what excellence looks like?</p></li><li><p>Have we coached before we corrected?</p></li><li><p>Have we walked alongside people before we evaluated them?</p></li><li><p>Have we created opportunities for growth, or have we simply documented the lack of it?</p></li></ul><p>The chair does not give us permission to become professional critics. It calls us to become faithful stewards.</p><p>That means investing in people before evaluating them. It means correcting with dignity. It means refusing to confuse authority with influence. It means recognizing that every adult in the building is someone&#8217;s investment, just as every child is.</p><p>But let me be equally clear. Stewardship is not endless tolerance. There comes a point when continued investment is met with continued resistance. There comes a point when grace has been extended, support has been provided, expectations have been clarified, and opportunities have been created.</p><p>If nothing changes, the leader has another responsibility.</p><ul><li><p>To protect the mission.</p></li><li><p>To protect the culture.</p></li><li><p>To protect the people who are doing the work faithfully.</p></li></ul><p>Too many organizations have been damaged by leaders who were unwilling to confront what everyone else already knew.</p><p>Just as many have been damaged by leaders who confronted everything except themselves.</p><p>The chair requires enough humility to ask, <em>&#8220;Am I part of the problem?&#8221;</em></p><p>And enough courage to ask someone else the same question.</p><p>Both matter.</p><p>Because children deserve adults who are still willing to grow.</p><p><strong>If you&#8217;re standing beside the chair</strong>, hoping one day to sit in it, I hope this week&#8217;s reflection doesn&#8217;t discourage you. I hope it prepares you.</p><p>Before you ask for greater influence, ask yourself a harder question.</p><ul><li><p>Am I becoming the kind of adult I hope to one day lead?</p></li><li><p>When I receive feedback, do I explain it away? Or do I grow from it?</p></li><li><p>When expectations change, do I become adaptable? Or do I become resistant?</p></li><li><p>When accountability comes, do I see an attack? Or an opportunity?</p></li><li><p>When someone invests in me, do I honor that investment? Or do I expect more while giving the same?</p></li></ul><p>Because one day, if you&#8217;re blessed with the opportunity to sit in the chair, you won&#8217;t simply inherit a school. You&#8217;ll inherit people.</p><p>People with gifts. People with fears. People with blind spots. People with extraordinary potential. People who will disappoint you. People you&#8217;ll disappoint. People who need someone willing to believe in them. And people who will refuse every opportunity you offer.</p><p>The chair asks you to faithfully steward every one of them.</p><p>That is why it is bigger than you think.</p><p>I don&#8217;t want this week&#8217;s reflection to leave anyone thinking the goal is simply to become a stronger evaluator. It isn&#8217;t.</p><p>The goal is to become a stronger investor. A stronger coach. A stronger steward. Someone who is willing to pour into people long before asking them to pour more into the organization.</p><p>But also someone who understands that children should never inherit dysfunction because adults refused to confront it.</p><p>That is one of the hardest responsibilities the chair will ever ask you to carry.</p><p>And no title can prepare you for it. Only faithful stewardship can.</p><h1>The Heart of the Lesson</h1><p>The chair has taught me that schools are not transformed by finding different children. They are transformed as adults become more faithful to the children they have already been entrusted to serve.</p><p>That includes the teacher who chooses to grow instead of becoming comfortable. The veteran who decides they still have something to learn. The new teacher who receives correction without losing heart. The support staff member who understands that every interaction contributes to the culture of the building. The parent who chooses partnership over suspicion. The leader who refuses to lower expectations while refusing to stop believing in people.</p><p>All of us are shaping something. The chair simply makes you responsible for more of it.</p><p>That is why leadership feels so heavy. Not because everyone agrees with you. Because everyone matters.</p><p>The chair asks us to invest in people who may never thank us. To coach people who may resist us. To hold people accountable without forgetting their humanity. To extend grace without permitting dysfunction. To protect children without giving up on adults. And sometimes to accept that despite our best efforts, not everyone will choose to grow.</p><p>That is not failure. That is the reality of stewarding human beings.</p><p>I have come to believe that faithful leadership is not measured by how many people like us. Nor is it measured by how few complaints we receive.</p><p>It is measured by whether the people entrusted to our care were better served because we occupied the chair with humility, courage, consistency, and conviction.</p><p>The chair does not ask us to be perfect. It asks us to be faithful.</p><p>Faithful enough to pour into people. Faithful enough to tell the truth. Faithful enough to receive the truth ourselves. Faithful enough to remember that children are always watching the adults around them.</p><p>And faithful enough to understand that the culture they inherit tomorrow is being created by the adults we choose to be today.</p><h2>The Commission</h2><h3>For Those Already Sitting in the Chair</h3><p>We need to stop spending so much time talking about what children and parents are not doing while ignoring what adults have normalized around them.</p><p>Children do not set the instructional standard. Adults do. Children do not decide whether meetings are purposeful, whether feedback is received well, whether gossip spreads, whether accountability is consistent, or whether excellence is protected. Adults do. And the person sitting in the chair carries a particular responsibility for what those adults are permitted to practice.</p><p>That means we must look honestly at both ends of the spectrum.</p><p>Some leaders damage organizations because they are controlling, reactive, manipulative, inconsistent, or more interested in power than growth.</p><p>Other leaders damage organizations because they will not act.</p><p>They avoid. They delay. They hope the problem will resolve itself. They call fear grace. They call silence patience. They call inconsistency compassion. Meanwhile, everyone else learns that the standard is optional.</p><p>Current leaders, we must be willing to ask ourselves whether we have created the very resistance we are criticizing.</p><ul><li><p>Have we explained expectations clearly?</p></li><li><p>Have we invested before inspecting?</p></li><li><p>Have we poured into people before documenting what they failed to produce?</p></li><li><p>Have we rolled up our sleeves and helped create the quality we later demanded?</p></li><li><p>Or have we waited until the work was finished, pointed out everything wrong, and called that leadership?</p></li></ul><p>Anybody can identify the dust. The chair requires us to pick up the duster.</p><p>But once we have done that, once we have clarified, modeled, coached, supported, and allowed reasonable time for growth, we must stop pretending that every repeated shortfall is still a misunderstanding.</p><p>Some adults know the expectation. Some understand the impact. Some have received the support. And some still choose <em>not to change</em>.</p><p>That is where leadership becomes costly.</p><p>A teacher shortage does not make poor instruction harmless. Longevity does not transform dysfunction into tradition. Political connections do not make children less deserving of competent adults. Being well liked does not excuse a leader from protecting the mission. And grace should never become permission for children to inherit dysfunction.</p><p>We cannot control whether another adult chooses to grow. We can control whether we have led faithfully.</p><ul><li><p>Did we listen? </p></li><li><p>Did we teach? </p></li><li><p>Did we provide tools? </p></li><li><p>Did we confront the pattern? </p></li><li><p>Did we document support as carefully as we documented failure? </p></li><li><p>Did we remain fair regardless of friendship, influence, seniority, or personality? </p></li><li><p>Did we preserve the person&#8217;s dignity? </p></li><li><p>Did we protect the children and the organization?</p></li></ul><p>When the answer is <em>yes</em>, we must be willing to accept that stewardship does not always end in restoration. Sometimes it ends in release.</p><p>Not because the person has no value. Not because we are angry. Not because we have stopped caring. Because one adult&#8217;s continued resistance cannot become everyone else&#8217;s permanent burden.</p><p>Current leaders, stop lowering standards because adults are more uncomfortable to confront than children. Stop correcting the easiest person while avoiding the most connected person. Stop calling someone toxic simply because they challenge you. But also stop refusing to name toxicity when division, manipulation, resistance, and organizational harm have become an established pattern.</p><p>Control what you can control. Invest faithfully. Confront honestly. Act consistently. And when the evidence is clear, have the courage to make the decision the chair requires.</p><h3>For Those Standing Beside the Chair</h3><p>Before we ask for the chair, we need to understand what we are asking to inherit.</p><p>We are not simply asking for greater influence over children. We are asking to become responsible for the adults who shape their experience. That includes people who are older than we are. People with more experience. People with stronger relationships in the community. People who may have encouraged our leadership journey. People we admire. People we hire. People we genuinely love. And one day, the chair may require us to look across the table at one of them and say:</p><p><strong>&#8220;This cannot continue.&#8221;</strong></p><p>Aspiring leaders, prepare for that now. </p><p>Not by becoming harder. By becoming steadier.</p><ul><li><p>Learn how to receive feedback without explaining it away.</p></li><li><p>Learn how to separate correction from rejection.</p></li><li><p>Learn how to adjust when expectations change.</p></li><li><p>Learn how to take ownership when your intent was good but your impact was harmful.</p></li><li><p>Learn how to contribute to the culture you say you want before asking for authority to create it.</p></li></ul><p>The person standing beside the chair should not only study how leaders hold others accountable. We should examine how accountable we are now.</p><ul><li><p>When someone pours into us, do we respond with growth?</p></li><li><p>When we disagree with leadership, do we bring solutions or only criticism?</p></li><li><p>Do we help carry the work, or do we simply place X&#8217;s beside what others failed to do?</p></li><li><p>Are we becoming the kind of adult we would hope to inherit if the chair belonged to us tomorrow?</p></li></ul><p>Those questions matters because authority will not correct habits we refuse to confront before promotion.</p><p>The chair will not make us more humble. It will reveal whether humility was already being formed. It will not make us fair. It will expose the inconsistencies we have carried with us. It will not automatically teach us how to invest in people. That work must begin now.</p><p>Pour into the new teacher beside you. Help the colleague who is struggling. Model professionalism when no title requires it. Receive correction without collapsing. Challenge what is harmful without becoming harmful yourself. Learn to distinguish between what is annoying, what is malicious, and what is detrimental.</p><p>Not every person who frustrates us is toxic. Not every disagreement is disloyalty. Not every explanation is resistance. But repeated harmful behavior after support and correction should not be romanticized as a difficult season forever.</p><p>Aspiring leaders need enough compassion to recognize the humanity beneath a shortfall and enough discernment to recognize when the shortfall has become a habit.</p><p>Because one day, the chair will ask us to decide.</p><p>Another conversation? Another season of support? A formal plan? Or a necessary separation?</p><p>The chair is bigger than we think because no answer is painless. Another chance may affect children and colleagues. A separation may affect a family and a career. Doing nothing is still a decision. And someone will carry its consequences.</p><p>Prepare now to be the kind of leader who can carry those consequences without becoming cruel, passive, proud, or afraid.</p><p>The children will need our hearts. The adults will require our courage. The mission will demand both.</p><h1>Reflection for the Week</h1><p>As I leave the milk crate this week, these are the questions I find myself carrying.</p><h3>For those already sitting in the chair:</h3><ul><li><p>Have I invested in my people as intentionally as I have evaluated them?</p></li><li><p>Am I holding people accountable because I care about them and the children they serve, or because I simply want compliance?</p></li><li><p>Is there someone on my team who needs more coaching from me before they need more correction?</p></li><li><p>Have I tolerated something that has quietly become part of our culture?</p></li><li><p>Am I asking others to grow in areas where I have stopped growing myself?</p></li></ul><h3>For those standing beside the chair:</h3><ul><li><p>How do I respond when someone pours into me or challenges me to improve?</p></li><li><p>Am I becoming the kind of teammate I would hope to inherit if I were leading tomorrow?</p></li><li><p>Do I contribute to the culture I say I want, or do I quietly work against it?</p></li><li><p>Am I preparing to invest in people, or am I only preparing to supervise them?</p></li><li><p>If leadership is ultimately about stewarding adults for the sake of children, what can I begin practicing today without waiting for a title?</p></li></ul><p>And for all of us:</p><p><strong>What kind of adult are the children around me learning to become by watching me?</strong></p><p>That question may be worth sitting with for a while.</p><h2><strong>Join Us Weekly</strong></h2><p>Click &#8216;subscribe now&#8217; below to join us weekly for these free reflections.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h1>Recognition</h1><p>As I leave the milk crate this week, I find myself grateful for the leaders who understood that their greatest work was never simply managing schools.</p><p>They invested in people. They poured into teachers long before those teachers ever led classrooms of their own. They challenged colleagues they cared enough not to ignore. They extended grace without abandoning standards. They held the line when it would have been easier to look the other way. Most importantly, they understood that every adult in the building was helping write the story children would eventually remember.</p><p>I have also become deeply grateful for the adults who accepted that investment. The mentors who kept learning. The teachers who welcomed coaching. The colleagues who were willing to hear difficult truths without allowing them to become personal attacks. The staff members who quietly made everyone around them better simply because they never stopped growing. They remind me that leadership is never a one-person effort. Healthy cultures are built by adults who choose, every day, to keep becoming.</p><p><strong>Before we leave the milk crate this week</strong>, I want to leave you with one final thought: long after children forget the lesson we taught on Tuesday afternoon, they will remember the adults who taught them what integrity looked like.</p><p>Long after our names disappear from office doors, classrooms, and organizational charts, the culture we helped create will still be teaching the people who remain.</p><p>That is the stewardship of the chair. That is why the chair is bigger than we think.</p><p>Pull up a milk crate with us again next Saturday as we continue our journey through <strong>Before You Sit in the Chair: Why Leadership Is Bigger Than You Think.</strong></p><p>Next week, we&#8217;ll reflect on another truth that aspiring leaders rarely hear before they inherit the responsibility themselves. Until then, don&#8217;t spend this week asking whether the adults around you need to change.</p><p>Spend this week asking a more difficult question:</p><p><strong>Am I becoming the kind of adult I would want helping shape the culture of the children I love most?</strong></p><p>Because schools are rarely held back by children alone. More often than not, they are held back by the adults entrusted to lead, teach, support, and shape them.</p><p><strong>And that matters more than we know.</strong></p>]]></content:encoded></item><item><title><![CDATA[Everyone Needs Something From the Chair]]></title><description><![CDATA[Before You Sit In The Chair: Why Leadership Is Bigger Than You Think Part III]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/everyone-needs-something-from-the</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/everyone-needs-something-from-the</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 18 Jul 2026 12:03:34 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/20a2f074-ff42-4a99-8051-f741c5934dfb_1122x1402.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>The <a href="https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters">milk crate</a> was never occupied by only one version of the day.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!aE9Y!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!aE9Y!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!aE9Y!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!aE9Y!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!aE9Y!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!aE9Y!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg" width="1122" height="1402" 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srcset="https://substackcdn.com/image/fetch/$s_!aE9Y!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!aE9Y!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!aE9Y!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!aE9Y!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F515b579d-8815-407a-8bb4-af19707c3ecd_1122x1402.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>By the time we gathered around it, everyone had arrived carrying something. Someone was frustrated about transportation. Someone was worried about a child. Someone was replaying a difficult conversation with a parent. Someone was disappointed in an employee. Someone had spent the entire day trying to solve a problem that seemed determined to survive until tomorrow. And someone was simply tired enough to sit down without saying much at all.</p><p>Each concern was real. Each person had experienced the day from where they had been standing. But the milk crate had a way of placing our individual perspectives beside one another.</p><p>Sometimes another leader would tell a story that made our problem feel smaller. Sometimes someone asked a question that made us realize we had overlooked something. Sometimes laughter loosened our grip on a frustration we had been carrying too tightly. And sometimes we discovered that the person sitting beside us had been carrying something heavier all day and had never said a word.</p><p>The milk crate did not make our concern less important. It simply reminded us that our concern was not the only concern in the room.</p><p>Long before I sat in the principal&#8217;s chair, that old piece of plastic was teaching me something about leadership that I did not yet have the experience to understand:</p><blockquote><p><strong>Where we stand shapes what we see.</strong></p></blockquote><p>Before we sit in the chair, most of us are responsible for a part. A classroom. A department. A program. A child. A concern. A particular group of people. But once we sit in the chair, we become responsible for how all those parts affect one another.</p><p>We have already been sitting with the truth that <strong><a href="https://lessonsfromthemilkcrate.substack.com/p/before-you-sit-in-the-chair-why-leadership">the chair is bigger than it first appears</a></strong>, and that <strong><a href="https://lessonsfromthemilkcrate.substack.com/p/you-interview-every-day">we are formed for its weight long before anyone offers us the title</a></strong>. This week carries both truths one step further: preparation for leadership must include learning to see beyond the part of the organization closest to us.</p><p>That is where this week begins. Because everyone needs something from the chair.</p><p>And nearly everyone approaches it through the part of the whole they can see.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!xkSL!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!xkSL!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!xkSL!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!xkSL!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!xkSL!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!xkSL!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg" width="1024" height="1024" 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srcset="https://substackcdn.com/image/fetch/$s_!xkSL!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!xkSL!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!xkSL!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!xkSL!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd8ebd945-715a-429f-b871-5839e3258e33_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>What This Week Understands</h2><p>This week understands that <strong>having a clear perspective is not the same as having a complete perspective</strong>.</p><p>That can be difficult to accept.</p><p>When we are close to a problem, we often believe we understand it best. We have lived with it. We have watched it develop. We have experienced the consequences. We may have spent weeks, months, or even years thinking about what should be done. And we may be right about much of what we see.</p><p>But being right about our part does not mean we can see the whole.</p><p>The teacher sees the classroom. The parent sees the child. The student sees the experience or the consequence. The employee sees the personal circumstance. The supervisor sees the outcome. The community sees the reputation. </p><p>Each perspective may contain truth. Each concern may be legitimate. Each person may have good reason to believe the matter deserves immediate attention. </p><p>But leadership requires more than recognizing the need closest to us. It requires considering the people who may never enter the room where the decision is made.</p><p>This week also understands that <strong>the chair does not give anyone perfect vision</strong>.</p><p>Authority does not create wisdom. A title does not eliminate blind spots. The person sitting in the chair can still misunderstand, assume, overlook, and make mistakes. Sometimes leaders see more of the picture and still reach the wrong conclusion.</p><p>The chair does not make us all-knowing. It makes us responsible for seeking a wider view. That distinction matters.</p><p>A leader cannot simply say, &#8220;You do not understand the bigger picture,&#8221; as a way of dismissing every concern raised from outside the chair. The person standing beside us may see the very thing we have missed.</p><p>At the same time, the person carrying one concern cannot assume that concern should automatically become the direction of the entire organization.  Strong feelings do not create complete understanding. Proximity to a problem does not guarantee wisdom about its solution. And seeing one issue clearly does not mean we can see every consequence that may follow from addressing it the way we prefer.</p><p>Finally, this week understands one more thing:</p><p>Listening to every perspective does not mean carrying every perspective as direction. Listening is not agreement. Understanding is not adoption. Empathy is not surrender.</p><p>The chair must hear the parts.</p><p>But it must lead for the whole.</p><h2>A Lesson Along the Way</h2><p>I remember becoming frustrated during my early years in administration.</p><p>I had become fixated on a problem. From where I sat, the issue appeared clear. I understood what was happening. I believed I understood why it was happening. And I had a strong opinion about what needed to happen next. I could see the problem. At least, I could see the portion of it directly in front of me.</p><p>I remember sitting beside S.W. on the milk crate and explaining what I believed should be done. I was confident in my reasoning. I had considered the information available to me. And I believed my approach was wise. S.W. listened. He did not dismiss me. He did not make me feel foolish for having an opinion. He did not use his experience to embarrass my inexperience. Instead, he acknowledged that what I saw made sense from where I was standing.</p><p>There was wisdom in my perspective. There was truth in what I had noticed. Then he helped me see what my position had not yet required me to consider.  There were other people affected. Other responsibilities involved. Other consequences that might follow. There were parts of the situation I could not see because I had been looking at the problem from only one side of the chair.</p><p>S.W. did not tell me that I was entirely wrong. He showed me that I was incomplete.</p><p>That distinction stayed with me.</p><p>I had mistaken a clear view of one side for a complete view of the whole. Standing beside the chair, I could see what was directly in front of me. But the person sitting in the chair was responsible for what was in front, what was beside, what was behind, and what might be waiting around the corner after the decision was made.</p><p>My perspective had not been useless. It simply needed to be widened. That moment did not diminish my vision. It disciplined it.</p><p>And years later, after sitting in the chair myself, I understand more clearly what S.W. was trying to teach me:</p><p>Almost everyone who approaches the chair sees something real.</p><p>But rarely does any one person see everything the chair must consider.</p><h2>Let&#8217;s Sit With That for a Moment</h2><p>Some of us begin aspiring to leadership because we are frustrated.</p><p>We see decisions we would make differently. We notice problems others appear unwilling to address. We sit in meetings quietly rehearsing what we would do if the authority belonged to us. We tell ourselves that if we ever receive the opportunity, things will be different.</p><p>And sometimes that frustration is evidence of vision. Sometimes we are seeing something others have overlooked. Sometimes courage really is forming in us.</p><p>But here is the uncomfortable truth:</p><div class="pullquote"><p><strong>Not every frustration with leadership is evidence that we are ready to lead.</strong></p></div><p>Sometimes it is evidence that we have not yet learned to see beyond the portion of the organization that affects us.</p><p>We may be right about the problem and still be wrong about the solution. We may understand the pain and still fail to understand the consequences. We may possess enough information to criticize the decision but not enough responsibility to understand why it was made.</p><blockquote><p><em>Criticism is inexpensive when someone else carries the consequences.</em></p></blockquote><p>It is easy to say what should happen when we will not have to explain it to the staff, defend it to the family, justify it to a supervisor, repair the unintended damage, or return the next morning and continue leading everyone affected by it.</p><p>That does not mean aspiring leaders should become silent. Leadership needs people willing to see what others miss. But conviction must be disciplined by humility.</p><p>The chair is not a reward for being right about our part. It is a responsibility to become accountable for the whole.</p><p>If our vision cannot survive questions, it is not ready for leadership. If our solution cannot be reconsidered when new information appears, it is not conviction-it is attachment. If we believe authority exists so that our perspective can finally win, we are not ready for the chair.</p><p>Leadership does not simply give us a louder voice. It gives us a wider responsibility.</p><p>But those of us already sitting in the chair must face an uncomfortable truth of our own: the title does not automatically widen our perspective. In fact, the chair can slowly narrow it.</p><p>People may stop disagreeing openly. They may tell us what they believe we want to hear. They may nod in meetings and speak honestly only after we leave the room. We can begin mistaking silence for agreement. Compliance for trust. Authority for wisdom. And before long, we may convince ourselves that we see the whole simply because we are the ones authorized to make the decision. That is dangerous.</p><p>The phrase, &#8220;You do not understand the bigger picture,&#8221; may sometimes be true. It can also become a convenient hiding place for leaders who do not want their thinking questioned. Confidentiality is real. Some information must be protected. But confidentiality cannot become an excuse for arrogance, poor communication, isolated decision-making, or refusing to explain the values and reasoning behind our work.</p><p>We may not be able to share every detail. We can still explain the process. We can name the principles that guided us. We can acknowledge the competing needs. We can clarify what the mission required. We can admit what the decision cost. And we can confess when someone standing outside the chair has seen something we missed.</p><p>If no one around us can question our perspective without being labeled negative, resistant, disloyal, or uninformed, then we have not built a leadership culture. We have built an echo chamber. And an echo chamber may protect our confidence while quietly damaging the organization.</p><p>Still, the chair cannot become a collection of everyone else&#8217;s preferences.</p><p>Leadership is not a weekly vote on which expectation should become the mission. It is not surrendering direction every time someone becomes disappointed. At some point, after the questions have been asked, the voices have been heard, and the consequences have been weighed, the person sitting in the chair must decide.</p><p>Not according to ego. Not according to popularity. Not according to the loudest voice. According to the mission, the evidence, the values of the organization, and the good of the whole.</p><p>The chair must hear the parts.</p><p>But it must lead for the whole.</p><h2>The Responsibility We Share</h2><p>This series is written especially for those preparing to sit in the chair.</p><p>And one of the most important things aspiring leaders must understand is that the chair is not simply where we get to make decisions. It is where we become responsible for everything surrounding those decisions.</p><p>The reactions. The questions. The disappointments. The misunderstandings. The consequences we anticipated. And sometimes the consequences we never saw coming.</p><p>That responsibility is difficult to reproduce in a textbook.</p><p>A graduate program can teach policy. A course can teach theory. A leadership academy can provide frameworks. Those things matter. But no discussion board can fully reproduce the weight of making a decision that affects an entire staff, a student, a family, or a community and then returning the next morning to lead the people who disagreed with it.</p><p>That is why current leaders have a responsibility beyond making decisions well.</p><p>We must help aspiring leaders understand how decisions are considered. Not confidential information they are unable to receive. Not private details that belong to someone else. But the thinking behind the work.</p><ul><li><p>Who is affected?</p></li><li><p>What needs are competing?</p></li><li><p>What happens if we say yes?</p></li><li><p>What happens if we say no?</p></li><li><p>What precedent might this create?</p></li><li><p>How does this align with the mission?</p></li><li><p>What are we seeing that others may not see?</p></li><li><p>And what might others be seeing that we have missed?</p></li></ul><p><strong>Current leaders</strong>, we cannot complain that aspiring leaders see only part of the picture if we have never invited them close enough to understand how the whole is considered.</p><div class="pullquote"><p><em><strong>Mystery is not mentorship.</strong></em></p></div><p>Telling someone, &#8220;You just do not understand,&#8221; may end the conversation. It does not form the leader. S.W. did something better for me. He honored what I saw and then helped me see more.</p><p>That is our responsibility.</p><p>Do not use experience to silence the vision developing in someone else. Use experience to widen it.</p><p>Invite aspiring leaders into the thinking. Ask what they see before telling them what they have missed. Let them wrestle with competing needs. Allow them to consider what a decision may cost. Explain what can be explained. Show them where your thinking changed. Tell them when you got it wrong. Let them see that leadership is not the performance of certainty. It is the discipline of seeking wisdom while carrying responsibility.</p><p>And when an aspiring leader identifies something we have missed, receive it without using the title to defend our pride. The people standing beside the chair do not need us to prove how little they know. They need us to help them understand how much more there is to see. And sometimes, we need them to help us see what the chair has made too easy to overlook.</p><p><strong>Aspiring leaders</strong> carry responsibility too.</p><p>Bring your perspective. Name what you see. Ask the hard question. Challenge the practice that no longer serves people well.</p><p>But do not mistake frustration for complete understanding.</p><p>Do not assume that because a decision does not make sense to you, no thoughtful reasoning exists behind it. Do not confuse proximity to one problem with readiness to direct the entire organization. And do not become the kind of aspiring leader who can identify everything wrong while accepting responsibility for nothing difficult.</p><p>Critique without responsibility can feel courageous. Sometimes it is simply comfortable. Before declaring what the chair should do, ask what your preferred solution will cost.</p><ul><li><p>Who else will be affected?</p></li><li><p>What precedent will it create?</p></li><li><p>What other responsibility might be compromised?</p></li><li><p>What happens six months after the immediate relief?</p></li><li><p>What information may be missing?</p></li><li><p>What would happen if the people who currently agree with you became the ones most disappointed by your decision?</p></li></ul><p>That last question matters.</p><p>Because some of the people encouraging us to pursue leadership will become frustrated with us once our responsibility includes holding them accountable. The same colleagues who applaud our vision may question our motives when the standard reaches them. The same people who say, &#8220;We need someone willing to make hard decisions,&#8221; may decide the decision was too hard when it affects their comfort.</p><p>Prepare for that.</p><p>Not by becoming cold. By becoming grounded. Learn to be questioned without collapsing. Learn to reconsider without losing confidence. Learn to hold conviction without worshiping your own opinion. Learn to hear &#8220;no&#8221; without immediately assuming incompetence, indifference, or conspiracy. Learn to recognize that sometimes a leader made the best decision available and we simply did not receive the outcome we preferred.</p><p>One day, the chair may belong to us.</p><p>When it does, we may discover that leadership is not the freedom to do what we always believed should be done.</p><p>It is the responsibility to consider what our former position never required us to carry.</p><h2>The Heart of the Lesson</h2><p>Everyone needs something from the chair.</p><p>Every person approaches it carrying a concern shaped by what they see, what they need, and what they fear may be lost.</p><p>The aspiring leader may believe the problem is that current leadership cannot see what they see. The current leader may believe the problem is that everyone else simply cannot understand the chair.</p><p>Both may be partly right. Both may also be protecting themselves from a harder truth.</p><p>Aspiring leaders can become so certain of their perspective that they confuse criticism with readiness.</p><p>Current leaders can become so certain of their authority that they confuse position with wisdom.</p><p>The chair will expose both.</p><p>It will reveal whether we can allow our ideas to be questioned. It will reveal whether we can listen without becoming defensive. It will reveal whether we can change our minds without feeling diminished. It will reveal whether we can hear disagreement without surrendering direction. It will reveal whether we genuinely want the whole to improve or merely want our own judgment validated.</p><p>The chair is not the place where our perspective finally defeats everyone else&#8217;s. Neither is it the place where every perspective receives the outcome it prefers.</p><p>It is a place of stewardship.</p><p>We hear the parts. We seek the whole. We weigh what is true. We protect the mission. And then, with humility, we decide.</p><p>Someone may still disagree. Someone may still feel disappointed. Someone may still believe we failed to understand. But leadership cannot be measured by whether everyone approves of the decision.</p><p>It must be measured by whether we listened honestly, considered broadly, acted ethically, and remained accountable for what followed.</p><p>Before we sit in the chair, we often see what affects us. Once we sit in it, we become responsible for what affects everyone. And once we sit there long enough, we must guard against believing that responsibility makes our vision complete. It does not.</p><p>The chair must hear the parts.</p><p>But it must lead for the whole.</p><h2>The Commission</h2><h3>For Those Already Sitting in the Chair</h3><p>We need to ask ourselves questions that may make us uncomfortable.</p><ul><li><p>Have we confused our position with superior perspective?</p></li><li><p>Have we surrounded ourselves with people who sharpen our thinking or people who protect our comfort?</p></li><li><p>Do people tell us the truth before decisions are made, or only whisper it after the meeting?</p></li><li><p>Do we invite input because we value it, or because we want people to feel included after we have already decided?</p></li><li><p>Have we ever used confidentiality to avoid explaining what could have been explained?</p></li><li><p>Have we labeled someone resistant when they were actually revealing a blind spot?</p></li><li><p>Have we dismissed an aspiring leader&#8217;s concern because the delivery lacked polish, even though the observation contained truth?</p></li></ul><p>The chair does not make our assumptions sacred. It does not make our motives unquestionable. It does not make disagreement disrespectful. And it does not excuse us from examining the culture we have created around our leadership.</p><p>If everyone around us always agrees, we should not immediately congratulate ourselves. We should wonder whether people still feel safe enough to tell us the truth.</p><p>Invite someone closer this week. Not simply to observe the outcome. Invite them into the reasoning. Ask what they see. Let them wrestle with the competing needs. Show them where your own thinking is incomplete. Explain what can be explained. And when their perspective reveals something you missed, have enough security to say so.</p><p>The future of leadership will not be strengthened by leaders who make themselves appear infallible.</p><p>It will be strengthened by leaders humble enough to teach, listen, reconsider, and remain accountable.</p><h3>For Those Standing Beside the Chair</h3><p>Bring your vision. The organization may need it. Bring your questions. The chair may have overlooked something. Bring your courage. Some practices deserve to be challenged. But bring humility too.</p><p>Do not confuse one clear angle with the entire landscape. Do not assume that your frustration proves your readiness. Do not mistake criticism for courage when you are unwilling to carry the consequences of the answer you are proposing.</p><p>Ask what you cannot yet see. Seek the voices beyond your own circle. Consider the people who are not in the room. Study not only what leaders decide, but what they must carry after the decision is made. </p><ul><li><p>Prepare yourself for the day when the people who once applauded your ambition become disappointed by your leadership.</p></li><li><p>Prepare to be misunderstood without becoming bitter.</p></li><li><p>Prepare to be questioned without becoming fragile.</p></li><li><p>Prepare to change your mind without losing your confidence.</p></li><li><p>Prepare to remain steady without becoming stubborn.</p></li></ul><p>The chair does not need leaders with no convictions.</p><p>It needs leaders whose convictions are strong enough to be examined.</p><h2>Reflection for the Week</h2><p>As we sit with this week&#8217;s reflection, let&#8217;s marinate on a few things:</p><h3>For Those Already Sitting in the Chair</h3><ul><li><p>Have I confused authority with complete understanding?</p></li><li><p>Do people feel safe enough to tell me what I may be missing?</p></li><li><p>Am I inviting aspiring leaders into the reasoning behind decisions, or only showing them the final answer?</p></li><li><p>Have I ever labeled a person resistant because their perspective made me uncomfortable?</p></li><li><p>When better information emerges, am I humble enough to reconsider?</p></li></ul><h3>For Those Standing Beside the Chair</h3><ul><li><p>Have I mistaken frustration with leadership for readiness to lead?</p></li><li><p>Am I right about the problem but incomplete about the solution?</p></li><li><p>Who else would be affected by the decision I believe is obvious?</p></li><li><p>Am I willing to let my vision be questioned, widened, and disciplined?</p></li><li><p>Do I want the responsibility of leadership or the validation of finally being in charge?</p></li></ul><h3>For All of Us</h3><ul><li><p>Can we honor the person standing in front of us without losing sight of everyone who is not in the room?</p></li></ul><p>That question may be worth carrying for a while.</p><h2>Join Us Weekly</h2><p>Click &#8216;subscribe now&#8217; below to join us weekly for these free reflections.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2>Recognition</h2><p>This week, I find myself especially grateful for S.W.</p><p>He could have used that milk crate moment to prove how little I knew. Instead, he helped me see more. He acknowledged the wisdom in my perspective without allowing me to remain trapped inside it. </p><p>He did not extinguish the conviction forming in me. He disciplined it. That is a gift.</p><p>Some mentors correct our answers. The best mentors expand our questions. They do not embarrass our inexperience. They help us understand that leadership requires more than certainty about what we see. It requires humility about what we do not.</p><p>S.W. taught me that being incomplete was not the same as being incapable. It simply meant I was still being formed. Years later, I continue returning to that lesson.</p><p>The chair has shown me more sides of leadership than I knew existed while standing behind it. And even now, I know there are parts of the whole I will miss unless I remain humble enough to listen.</p><p>For that milk crate conversation, and for the many leaders who helped me see beyond myself, I remain grateful.</p><h2>This Week</h2><p>Before next Saturday, I invite those already sitting in the chair to ask one trusted person:</p><p><strong>&#8220;What might I be missing?&#8221;</strong></p><p>Then listen. Do not explain. Do not defend. Do not correct the answer before it has had time to settle.</p><p>For those standing beside the chair, take one leadership decision you strongly question and ask:</p><p><strong>&#8220;What responsibility may exist beyond the part I can see?&#8221;</strong></p><p>That question may not change our conclusion. But it may change the spirit in which we carry it.</p><p>Current leaders, invite an aspiring leader into the reasoning behind one meaningful decision. Aspiring leaders, ask a trusted leader to help you see one consequence your preferred solution might create.</p><p>The goal is not to weaken conviction. It is to deepen it. Because the chair does not need leaders who see nothing clearly. It needs leaders who can see one thing clearly without pretending there is nothing else to see.</p><p>Next Saturday, we will continue this journey by confronting another difficult reality of leadership:</p><p><strong>The hardest person we are called to lead is not always a child.</strong></p><p>Until then, may we listen without surrendering responsibility. May we decide without worshiping our own perspective. May we remain open enough to learn and grounded enough to lead because:</p><p><strong>The chair must hear the parts.</strong></p><p><strong>But it must lead for the whole.</strong></p><p>And that matters more than we know.</p>]]></content:encoded></item><item><title><![CDATA[You Interview Every Day...]]></title><description><![CDATA[Before You Sit In The Chair: Why Leadership Is Bigger Than You Think Part II]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/you-interview-every-day</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/you-interview-every-day</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 11 Jul 2026 13:02:36 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!wVPb!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p><span>I used to think leadership interviews were about convincing someone else that I was ready. Maybe that is because interviews have a way of becoming milestones in our minds.</span></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!wVPb!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!wVPb!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!wVPb!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!wVPb!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!wVPb!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!wVPb!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg" width="1122" height="1402" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/a62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1402,&quot;width&quot;:1122,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:109795,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/205287656?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!wVPb!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!wVPb!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!wVPb!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!wVPb!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa62de418-0be0-4496-aa59-f0fd8bfb7c59_1122x1402.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><span>We remember the pressed suit hanging on the closet door the night before. We remember rehearsing answers while driving down the road, quietly practicing how we might respond if they ask about school culture, difficult conversations, instructional leadership, parent concerns, or what we would do in the first ninety days.</span></p><p><span>We remember sitting in the waiting room pretending to look calm while our minds are moving a mile a minute.</span></p><p><span>Did I prepare enough? Do I have enough experience? Will they see what I believe I can offer? Am I ready for this?</span></p><p><span>Interviews have a way of making us believe everything has been leading to that one moment. The handshake. The questions. The answers. The eye contact. The careful attempt to sound confident without sounding arrogant. Prepared without sounding rehearsed. Visionary without sounding unrealistic. Humble without sounding unsure.</span></p><p><span>And I understand that. I have lived that-most of us have.</span></p><p><span>But as I look back now, some years into sitting in the principal&#8217;s chair, I realize something that I could not have fully understood then: </span><strong><span>t</span></strong><em><strong><span>he interview was not where leadership preparation began</span></strong></em><span>.</span></p><p><span>Not even close.</span></p><p><span>The interview may have opened a door, but it did not form the person who walked through it. That formation started much earlier.</span></p><p><span>It started in ordinary days, oftentimes sitting on an </span><a href="https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters"><span>old milk crate</span></a><span>. In offices where I sat quietly because I had more to learn than to say. In conversations I only half understood at the time. In late afternoons when someone trusted me enough to let me see the work behind the work. In watching leaders make decisions that were far heavier than they looked from the outside. In learning that leadership is not just what we say when people ask us questions.</span></p><p><span>It is what has been forming in us long before anyone ever asks. And that is where this week begins. Because before we ever sit in the chair, most of us have already been showing people who we are.</span></p><p><span>Long before the formal interview. Long before the application. Long before the title. Long before anyone calls us leader. We have already been becoming something.</span></p><p><span>The question is whether or not we have been becoming someone prepared to carry responsibility well.</span></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!8Y8x!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!8Y8x!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!8Y8x!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!8Y8x!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!8Y8x!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!8Y8x!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg" width="1024" height="1024" 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srcset="https://substackcdn.com/image/fetch/$s_!8Y8x!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!8Y8x!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!8Y8x!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!8Y8x!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F94784132-5cfc-4b31-beec-722e4f535eac_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong><span>What This Week Understands</span></strong></h2><p><span>This week is not really about interviews.</span></p><p><span>Interviews matter. Preparation matters. Professional learning matters. Degrees matter. Certifications matter. Experience matters. Learning how to communicate our story matters.</span></p><p><span>There is nothing wrong with preparing well when an opportunity presents itself. In fact, I believe we ought to prepare well. We ought to take opportunities seriously. We ought to study, reflect, rehearse, and present ourselves with professionalism when someone gives us the privilege of being considered for greater responsibility.</span></p><p><span>But this week understands something deeper: </span></p><div class="pullquote"><p><em><strong><span>We can become so focused on preparing for the interview that we forget to prepare for the responsibility</span></strong></em><strong><span>.</span></strong></p></div><p><span>And those are not the same thing. Preparing for an interview teaches us how to answer questions. Preparing for responsibility teaches us how to live with consequences. Preparing for an interview teaches us how to describe leadership. Preparing for responsibility teaches us how to carry people. Preparing for an interview teaches us how to explain what we believe. </span></p><p><span>Preparing for responsibility teaches us whether we actually believe it enough to live it when it costs us something. That is a different kind of preparation. A quieter kind. A longer kind. A kind that does not always come with recognition.</span></p><p><span>And maybe that is why so many of us miss it. We often think leadership begins when someone finally notices us. When they call our name. When they offer the position. When the board approves the appointment. When the office door has our name on it.</span></p><p><span>But leadership begins long before leadership is recognized. It begins in the habits we practice when there is no audience. It begins in the way we respond to correction. It begins in whether we follow through when no one reminds us. It begins in whether we are dependable when the work is boring. It begins in whether we are teachable when we think we already know. It begins in whether we can be trusted with small responsibilities before we ask to carry larger ones.</span></p><p><span>That is what this week understands-not that interviews are unimportant, but that interviews are often the public recognition of private formation.</span></p><p><strong>Last week, we wrestled with the realization that <a href="https://lessonsfromthemilkcrate.substack.com/p/before-you-sit-in-the-chair-why-leadership">the chair never creates the leader-it simply reveals the person who has been forming all along</a>.</strong> If that&#8217;s true, then this week&#8217;s question becomes unavoidable:</p><p><strong>When does that formation begin?</strong></p><h2><strong><span>A Lesson Along the Way</span></strong></h2><p><span>During my formative years, </span><em><span>Doc</span></em><span> said something to me that stayed with me.</span></p><p><span>At the time, I thought I understood it. I did not.</span></p><p><span>She said: </span></p><div class="callout-block" data-callout="true"><p><strong><span>&#8220;You interview every day for the job you don&#8217;t even know you want.&#8221;</span></strong></p></div><p><span>Now, when I first heard that, I thought she was talking about professionalism. And to be fair, she was.</span></p><p><span>Show up on time. Dress like you take the work seriously. Treat people with respect. Do what you say you are going to do. Do not walk around creating mess and then expect other people to clean it up and still trust you with responsibility. Do not be lazy for years and then suddenly become impressive when a job posting appears or district office leadership are in the building. </span><strong><span>Do not confuse proximity to leadership with preparation for leadership.</span></strong></p><p><span>Those were obvious lessons, and they mattered. But I understand now that she was teaching something much deeper than professionalism.</span></p><p><span>She was talking about character. She was talking about formation. She was talking about the quiet reality that people are always becoming something in front of us.</span></p><p><span>Not through speeches. Not through r&#233;sum&#233;s. Not through interview answers.</span></p><p><span>But through patterns.</span></p><p><span>Patterns of dependability. Patterns of humility. Patterns of growth. Patterns of ego. Patterns of excuse-making. Patterns of service. Patterns of avoidance. Patterns of courage. Patterns of comfort. Patterns of accountability.</span></p><p><span>And whether we realize it or not, those patterns are speaking long before we ever sit across from an interview committee.</span></p><p><span>I think back now on how much I was allowed to see before I understood what I was seeing. </span><em><span>Doc</span></em><span> invited me into work that, at the time, I thought was simply administrative training.</span></p><p><span>Master scheduling. Budgets. Course counts. Staffing decisions. Discipline hearings. Parent conversations. Planning meetings. Testing discussions. The kind of work that never looks glamorous from the outside, but holds entire schools together from the inside.</span></p><p><span>At the time, I thought I was learning tasks. Now I understand I was learning judgment.</span></p><p><span>Master scheduling was not just about placing names into slots. It was about understanding priorities.</span></p><p><span>Who needs what? Where are the gaps? What does the data tell us? What does the data fail to tell us? How do we build a schedule that serves children rather than simply making adults comfortable?</span></p><p><span>Budgets were not just about numbers. They were about stewardship.</span></p><p><span>What do we value? What are we willing to invest in? What can wait? What cannot? What decision today will either limit or expand opportunity tomorrow?</span></p><p><span>Discipline was not just about consequences. It was about conviction.</span></p><p><span>Can we hold children accountable while still believing in them? Can we refuse to excuse behavior without refusing to love the child? Can we protect the learning environment for everyone while still trying to help the one who disrupted it?</span></p><p><span>Parent meetings were not just about communication. They were about restraint.</span></p><p><span>Can we hear frustration without becoming defensive? Can we tell the truth without becoming cruel? Can we stand firm without becoming hard?</span></p><p><span>Personnel conversations were not just about management. They were about courage.</span></p><p><span>Can we address what needs to be addressed? Can we give feedback directly? Can we refuse to let adult comfort become more important than student need?</span></p><p><span>I did not have language for all of that then. I do now.</span></p><p><span>That is the strange gift of time. Sometimes wisdom is handed to us before experience gives us the ability to open it. And years later, when the chair becomes ours, we finally realize what someone was trying to place in our hands all along.</span></p><p><em><span>Doc</span></em><span> was not simply preparing many of us for a job. She was trying to teach us how to carry one.</span></p><p><span>There is a difference.</span></p><h2><strong><span>Let&#8217;s Sit With That for a Moment</span></strong></h2><p><span>If </span><em><span>Doc</span></em><span>&#8217;s words are true, then leadership preparation is happening all the time.</span></p><p><span>Not just in graduate programs. Not just in leadership academies. Not just in certification courses. Not just in interview workshops. Not just when we decide we are ready for the next step.</span></p><p><span>Leadership formation is happening in the ordinary. And that may be one of the most important truths we can sit with. Because most people do not become leaders suddenly. They become leaders gradually.</span></p><p><span>Quietly. Repeatedly. Through decisions that appear small at the time but slowly reveal who they are becoming.</span></p><ul><li><p><span>A person does not suddenly become accountable because they receive authority. A person who avoids accountability before the title will usually avoid it after the title (except now their avoidance affects more people).</span></p></li><li><p><span>A person does not suddenly become humble because someone promotes them. A person who could not receive feedback before leadership will often become even more defensive once authority protects their ego.</span></p></li><li><p><span>A person does not suddenly become disciplined because the office is larger. A person who lacked discipline when the responsibility was small will struggle when the responsibility becomes organizational.</span></p></li><li><p><span>A person does not suddenly become a servant because the title says leader. Service must already be forming in them.</span></p></li></ul><p><span>That is why I think we have to be careful with how we talk about leadership preparation. If we reduce preparation to credit hours or credentials, we miss character. If we reduce preparation to interviews, we miss formation. If we reduce preparation to titles, we miss stewardship.</span></p><p><span>Leadership is not simply a role we eventually step into. It is a way of being that should already be taking shape before the role ever arrives.</span></p><p><span>Now, let me be clear. This does not mean people have to be perfect before they lead. </span><em><strong><span>No one is</span></strong></em><span>. Certainly not me.</span></p><p><span>I am still learning. Still growing. Still reflecting on things I wish I had handled differently. Still replaying conversations. Still discovering weaknesses that leadership has a way of exposing.</span></p><p><span>But that is part of the point: </span><em><strong><span>Leadership does not require perfection. It requires formation.</span></strong><span> </span></em><span>It requires teachability. It requires enough humility to admit that even after we receive the title, we are still becoming.</span></p><p><span>And maybe that is where aspiring leaders and current leaders both have work to do:</span></p><ul><li><p><span>Those standing beside the chair must recognize that preparation begins before opportunity.</span></p></li><li><p><span>Those sitting in the chair must recognize that part of our responsibility is to create spaces where preparation can happen.</span></p></li></ul><p><span>Because if we believe leadership begins long before the interview, then we cannot wait until the job posting appears to start developing people. And we cannot wait until the interview is scheduled to start becoming someone worthy of trust.</span></p><p><strong><span>We need </span></strong><em><strong><span>apprenticeship</span></strong></em><span>. </span><em><span>Not performative shadowing</span></em><span>.</span></p><p><span>Not someone sitting in a meeting just to say they were there. Not busy work dressed up as leadership development. </span></p><p><em><span>Real</span></em><span> apprenticeship. The kind where someone gets to see how decisions are made. The kind where someone is trusted with responsibility and then coached through what happened. The kind where leaders explain the &#8220;why,&#8221; not just the &#8220;what.&#8221; The kind where future leaders see not only polished outcomes, but unfinished thinking. The kind where they witness failure, correction, adjustment, and reflection.</span></p><p><span>Because leadership is not learned only by watching people succeed. Sometimes leadership is learned by watching people recover. Watching them apologize. Watching them reconsider. Watching them hold a line. Watching them change their mind when wisdom requires it. Watching them stay steady when pressure comes.</span></p><p><span>That is formation. That is apprenticeship. That is the work behind the work. And if we are honest, many of us need more of that.</span></p><p><span>Not because people are incapable. But because responsibility deserves more than assumption.</span></p><p><span>Children deserve more than assumption. Teachers deserve more than assumption. Communities deserve more than assumption. Organizations deserve leaders who have been formed, not just selected.</span></p><p><span>And formation takes </span><em><span>time.</span></em></p><h2><strong><span>The Responsibility We Share</span></strong></h2><p><span>I do not want this reflection to become a criticism of our profession. That is not the spirit of the milk crate.</span></p><p><span>The milk crate was never a place where people gathered simply to complain. It was a place where people told the truth because they cared enough to see the work improve.</span></p><p><span>And the truth is, leadership development belongs to all of us.</span></p><p><span>Not just districts. Not just universities. Not just certification programs. Not just human resources. Not just interview committees. All of us.</span></p><p><span>If we are already sitting in leadership, then someone is learning from us whether we are intentional about it or not.</span></p><p><span>They are learning how we respond to pressure. They are learning how we talk about people when those people are not in the room. They are learning whether we avoid hard conversations or step into them. They are learning whether we blame others or accept responsibility. They are learning whether we protect children or protect comfort. They are learning whether we hoard knowledge or share it. They are learning whether our leadership is about stewardship or status.</span></p><p><span>That should humble us. Because whether we mean to or not, we are always teaching leadership.</span></p><p><span>The question is what lesson others are learning from us. And if we are aspiring to lead, then we cannot sit passively waiting for someone to invite us into development. We have a responsibility too.</span></p><p><span>Ask questions. Request feedback. Volunteer for the work that does not come with applause. Learn the systems no one else wants to learn. Sit quietly in rooms where you have more to absorb than contribute. Pay attention to how leaders think, not simply what they decide. Study the burden, not just the authority. And perhaps most importantly, become faithful where you already are.</span></p><p><span>Because leadership begins in stewardship of the present assignment. Not the future one.</span></p><p><span>This is where I think we sometimes get impatient. We want the next thing. The next role. The next opportunity. The next title. The next salary step. The next seat.</span></p><p><span>I understand that. Ambition is not always wrong. </span></p><blockquote><p><em><strong><span>But ambition that outruns formation becomes dangerous.</span></strong></em></p></blockquote><p><span>There is nothing wrong with wanting to grow. </span></p><blockquote><p><em><strong><span>There is something wrong with refusing to develop or be developed while demanding or expecting to be promoted.</span></strong></em></p></blockquote><p><span>There is nothing wrong with believing you have more to offer. </span></p><blockquote><p><em><strong><span>There is something wrong with neglecting the responsibility already in your hands because your eyes are fixed only on what comes next.</span></strong></em></p></blockquote><p><span>And this is where current leaders and aspiring leaders meet in the same responsibility:</span></p><ul><li><p><span>Current leaders must open doors for formation. Aspiring leaders must walk through those doors with humility.</span></p></li><li><p><span>Current leaders must create opportunities to learn. Aspiring leaders must treat those opportunities as sacred, not as stepping stones for visibility.</span></p></li><li><p><span>Current leaders must mentor. Aspiring leaders must remain teachable.</span></p></li></ul><p><span>Both matter.</span></p><p><span>Because if leadership is stewardship before it is authority, then preparation cannot be accidental. It must be intentional.</span></p><p><span>And it must begin long before the interview.</span></p><h2><strong><span>The Heart of the Lesson</span></strong></h2><p><span>The interview may open the door. But formation prepares us to walk through it. That is the lesson I keep returning to.</span></p><p><span>A strong interview may earn an opportunity. But character determines what we do with that opportunity once it arrives. A polished answer may impress a committee. But humility will determine whether we keep learning after the title is ours. A r&#233;sum&#233; may tell people where we have been. But our habits reveal who we have become.</span></p><p><strong><span>And leadership will eventually reveal all of it. That is what the chair does. It reveals.</span></strong></p><p><span>It reveals our discipline. It reveals our motives. It reveals our patience. It reveals our ego. It reveals our preparation. It reveals whether we were becoming a steward or simply pursuing a seat.</span></p><p><span>And maybe that is why </span><em><span>Doc</span></em><span>&#8217;s words still matter to me.</span></p><p><span>&#8220;You interview every day for the job you don&#8217;t even know you want.&#8221;</span></p><p><span>Because every day is forming us. Every day is revealing us. Every day is preparing us. Or exposing what we have refused to prepare. Leadership is formed long before it is recognized.</span></p><p><span>And when recognition finally comes, the title does not create the leader.</span></p><p><span>It simply reveals the formation that was already there.</span></p><h2><strong><span>The Commission</span></strong></h2><h3><strong><span>For Those Already Sitting in the Chair</span></strong></h3><p><span>If we are already sitting in the chair, then we have to ask ourselves a hard question:</span></p><p><span>Who is learning leadership by watching us?</span></p><p><span>Not who have we officially mentored. Not who has been assigned to shadow us. Not who is enrolled in a leadership program.</span></p><ul><li><p><span>Who is watching?</span></p></li><li><p><span>Who is listening?</span></p></li><li><p><span>Who is picking up our habits without us realizing it?</span></p></li><li><p><span>Who is learning how to handle conflict because they watched us handle it?</span></p></li><li><p><span>Who is learning how to treat staff because they listened to how we spoke about them?</span></p></li><li><p><span>Who is learning whether children come first because they watched what we protected when decisions got difficult?</span></p></li></ul><p><span>That is a sobering thought. Because our leadership is forming someone even when we are not trying to form them. So let us become intentional.</span></p><p><span>Invite someone closer. Not to perform mentorship. To actually develop them. Let them see the work behind the work. Do not just tell them what decision was made. Explain why. Explain what you considered. Explain what kept you up. Explain what you got wrong. Explain what you would do differently.</span></p><p><span>Let them see your humanity. Let them see that leadership is not confidence all the time. It is often uncertainty carried with courage. Let them see that good leaders ask questions. Let them see that strong leaders apologize. Let them see that accountability and compassion can live in the same room. Let them see how stewardship thinks.</span></p><p><span>And maybe most importantly, do not wait until you are leaving to start preparing someone else. Leadership that only protects the present but fails to prepare the future is incomplete stewardship.</span></p><p><span>If we have been blessed to sit in the chair, then part of our responsibility is making sure someone else is better prepared because they stood beside us.</span></p><h3><strong><span>For Those Standing Beside the Chair</span></strong></h3><p><span>If you are standing beside the chair, hoping one day to lead, do not despise the season of preparation.</span></p><p><span>Do not rush past it. Do not treat it as wasted time. Do not assume that because you are capable, you are finished being formed.</span></p><p><span>There is a difference between being gifted and being ready. There is a difference between having potential and having preparation. There is a difference between wanting leadership and being willing to be shaped by what leadership requires.</span></p><p><span>So use this season well.</span></p><p><span>Ask to learn the things no one sees. Ask to sit in on the work that does not look impressive. Ask someone to explain how budgets work. Ask how schedules are built. Ask why discipline decisions are made the way they are. Ask how leaders prepare for difficult conversations. Ask what mistakes they made early on. Ask what they wish they had known sooner. And then listen. Really listen. Not so you can repeat the language in an interview. Listen so it changes how you think.</span></p><p><span>Volunteer for the difficult assignment. Take the responsibility that does not come with recognition. Be dependable when the work is boring. Be teachable when correction comes. Be honest when you make mistakes. Become someone others trust before you ask to be placed in charge. Because when the interview finally comes, you will want more than polished answers.</span></p><p><span>You will want evidence that leadership has already been forming in you. Not performative evidence. Real evidence.</span></p><p><span>The kind that shows up in how you work.</span></p><p><span>How you serve. How you respond. How you grow. How you carry what has already been entrusted to you.</span></p><p><span>Do not wait for the chair to begin becoming a leader.</span></p><p><span>Start with what is already in your hands.</span></p><h2><strong><span>Reflection for the Week</span></strong></h2><p><span>As I sit with this week&#8217;s lesson, I find myself returning to questions that are not easy, but necessary.</span></p><p><em><strong><span>For those already sitting in the chair</span></strong></em><span>:</span></p><ul><li><p><span>Who is learning leadership from me right now, whether I realize it or not?</span></p></li><li><p><span>What invisible parts of leadership have I kept invisible because I was too busy carrying them alone?</span></p></li><li><p><span>Have I created space for others to understand how decisions are made, or have I only allowed them to see the final decision?</span></p></li><li><p><span>Am I developing successors, or am I simply managing responsibilities?</span></p></li><li><p><span>If someone led one day the way they currently see me lead, would I be proud of what they learned?</span></p></li></ul><p><em><strong><span>For those standing beside the chair</span></strong></em><span>:</span></p><ul><li><p><span>Am I more focused on preparing for an interview than becoming the kind of person leadership will require me to be?</span></p></li><li><p><span>What responsibility can I carry well right now without needing a title to validate it?</span></p></li><li><p><span>Am I teachable enough to learn from correction, or only eager enough to learn what helps me advance?</span></p></li><li><p><span>Whose leadership am I studying closely, and am I paying attention to their burden as much as their authority?</span></p></li><li><p><span>What ordinary habits are forming me right now, for better or worse?</span></p></li></ul><p><span>And for all of us: </span></p><ul><li><p><span>Are we treating leadership as something to obtain or something to become worthy of carrying?</span></p></li></ul><p><span>That question may be worth sitting with for a while.</span></p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong><span>Recognition</span></strong></h2><p><span>This week I find myself grateful for those </span><a href="https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters"><span>milk crate leaders</span></a><span> who did more than supervise me. They formed me.</span></p><p><span>And for this particular lesson, I think especially of Doc. Not simply because she said something memorable, though she certainly did. But because she lived the lesson behind the words. When she said, &#8220;You interview every day for the job you don&#8217;t even know you want,&#8221; she was not merely warning me to behave professionally.</span></p><p><span>She was inviting me to pay attention to who I was becoming. She gave me access before I had earned authority. She trusted me with learning before I fully understood the lesson. She allowed me close enough to see the work behind the work.</span></p><p><span>And now, years later, I understand the gift more clearly.</span></p><p><span>The greatest mentors do not simply prepare us to answer questions. They prepare us to carry responsibility. That is the kind of leadership I hope to practice. That is the kind of leadership I hope to pass on. And that is the kind of leadership our schools, organizations, churches, families, and communities still desperately need.</span></p><p><span>Leadership that forms others. Leadership that shares wisdom. Leadership that understands the future is being shaped long before the next interview ever begins.</span></p><p><span>Pull up a milk crate with us again next Saturday.</span></p><p><span>We will continue our journey through </span><strong><span>Before You Sit In The Chair: Why Leadership Is Bigger Than You Think</span></strong><span>, as we reflect on another lesson I wish someone had slowed down long enough to explain before I ever carried the weight myself.</span></p><p><strong>Until then, don&#8217;t spend this week thinking about your next interview. Spend it thinking about your next opportunity to learn or your next opportunity to teach. Somewhere around you is a future leader who needs someone willing to slow down long enough to explain the work behind the work. Be that person. Or find that person.</strong></p><p>Because wanting leadership and being prepared for leadership have never been the same thing.</p><p><strong>And that matters more than we know.</strong></p>]]></content:encoded></item><item><title><![CDATA[The Chair Was Always Bigger Than I Thought]]></title><description><![CDATA[Stories and Encouragement for School Leaders]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/before-you-sit-in-the-chair-why-leadership</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/before-you-sit-in-the-chair-why-leadership</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 04 Jul 2026 13:04:06 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/abcfd655-d07e-4898-9287-c84f35e83851_1122x1402.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Long before I ever sat in a principal&#8217;s chair, I learned some of the most important lessons about leadership in a place no leadership program would ever think to look.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!Z5cs!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!Z5cs!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!Z5cs!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!Z5cs!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!Z5cs!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!Z5cs!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg" width="1122" height="1402" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/a9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1402,&quot;width&quot;:1122,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:109795,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/202439188?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!Z5cs!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!Z5cs!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!Z5cs!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!Z5cs!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fa9b16446-5a5c-4d34-abf3-a26ce09e1410_1122x1402.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>It usually happened behind the school building. Near the bus loop. Sometimes beside the cafeteria loading dock. Usually sometime after four o&#8217;clock (though on bad transportation days, it might be closer to seven-thirty).</p><p>The workday was technically over, but anyone who has worked in education long enough knows contracts have very little to do with reality. Ties were loosened. Dress shoes had long since lost their shine from twenty thousand steps. Radios clipped to our hips had already gone silent a dozen times. Somewhere in the distance, another delayed route was inevitably running twenty minutes behind schedule.</p><p>And then someone would grab one of those <a href="https://lessonsfromthemilkcrate.substack.com/">old plastic milk crates</a> stacked against the wall, flip it over, and sit down.</p><p>Without anyone formally saying it, the debriefing would begin. Sometimes we laughed. Sometimes we complained. Sometimes we sat there quietly replaying the day.</p><p>Sometimes the conversation drifted toward students who worried us, teachers we were trying to help, frustrations with district decisions, or simply the quiet exhaustion that comes from spending your entire day carrying the emotions and needs of hundreds of other people.</p><p>At the time, I thought I was simply sharing space with experienced administrators at the end of long workdays. Looking back now, I realize I was receiving an education far more valuable than anything graduate school would eventually offer me.</p><p>Because around that milk crate, I was learning leadership. Or at least I thought I was.</p><p>Today, sitting in a principal&#8217;s chair myself, I have come to understand something uncomfortable. I was watching leadership. But I was not yet understanding leadership. Not even close.</p><p>Because some things only reveal themselves once the weight becomes yours to carry.</p><p>And some chairs always look much smaller when you&#8217;re standing beside them.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!w9EC!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!w9EC!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!w9EC!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!w9EC!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!w9EC!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!w9EC!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/e0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/202439188?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!w9EC!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!w9EC!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!w9EC!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!w9EC!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe0a28853-7b14-4f5f-911b-b6bbaf08c5b6_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>What This Week Understands</h2><p>This week understands something I have been quietly wrestling with for some time now:</p><p><em><strong>There is a dangerous difference between wanting leadership and understanding leadership.</strong></em></p><p>I want to be careful here because this is not a criticism of ambition. Ambition can be healthy.Growth is healthy. Professional aspiration is healthy.</p><p>Organizations need people willing to prepare themselves for greater responsibility and step forward when the moment requires it.</p><p>Every exceptional leader once stood exactly where someone else stands today-learning, growing, and preparing for responsibilities they did not yet fully understand.</p><p>Leadership has always required greater stewardship. And I&#8217;m not convinced we&#8217;ve been honest enough about that reality. And perhaps that&#8217;s where my concern begins.</p><p>Somewhere along the way, we&#8217;ve become remarkably good at preparing people to obtain leadership while spending far less time helping them understand what leadership will eventually cost them.</p><p>We teach interviews. We teach strategic planning. We teach data analysis. We teach organizational structures. We teach people how to sound like leaders.</p><p>But I&#8217;m not convinced we&#8217;ve spent enough time teaching people what leadership quietly asks them to surrender once the interview is over.</p><p>That isn&#8217;t a criticism. It&#8217;s simply a reality we need to acknowledge if we&#8217;re serious about preparing the next generation well.</p><p>And that requires that we stop and ask a much harder question:</p><p><strong>Do they understand what the chair is going to demand once they finally sit in it?</strong></p><p>Because leadership was never simply about earning greater authority.</p><h2>A Lesson Along the Way</h2><p>When I first entered administration, I honestly believed I had a pretty good understanding of what school leaders did.</p><p>After all, I had spent years watching them. I had watched difficult parent meetings. I had watched discipline hearings. I had attended leadership meetings, faculty meetings, and professional development sessions. I had seen master schedules come together, watched teachers celebrated and corrected, and listened as difficult decisions were communicated to faculty and staff.</p><p>From where I stood, it felt as though I had a front-row seat to leadership.</p><p>I was fortunate in ways I didn&#8217;t fully appreciate at the time. Very early in my career, I found myself surrounded by extraordinary leaders. Not average administrators. Not placeholders. Not people simply occupying offices.</p><p>These were leaders who understood children deeply. They protected culture fiercely. They held adults accountable without humiliating them. They navigated impossible expectations with remarkable steadiness. They made extraordinarily difficult work appear remarkably ordinary.</p><p>Because I watched them every day, I convinced myself I understood leadership.</p><p>I thought I understood decision-making. I thought I understood pressure. I thought proximity had somehow given me understanding. It hadn&#8217;t.</p><p>The truth is, I was seeing only the visible parts.</p><p>I saw confident conversations. I didn&#8217;t see the sleepless nights that often came before those conversations. I saw decisive leadership. I didn&#8217;t see the internal wrestling that preceded difficult decisions. I saw authority. I didn&#8217;t yet recognize stewardship. I saw confidence. I didn&#8217;t yet recognize sacrifice. Most of all, I saw leaders who carried enormous responsibility so faithfully that they made leadership appear almost effortless.</p><p>Looking back now, I realize that may have been one of the greatest gifts they ever gave me. They were quietly absorbing burdens I wasn&#8217;t yet mature enough to carry. The better they led the easier leadership appeared to those standing beside them.</p><p>Perhaps that&#8217;s one of leadership&#8217;s greatest ironies:</p><p><em><strong>The better someone carries the burden the less visible the burden becomes.</strong></em></p><p>Then there is another truth I&#8217;ve reflected on often: I never aggressively pursued becoming a principal. That wasn&#8217;t some lifelong ambition carefully mapped out years in advance. Truthfully, I had convinced myself I needed much more time.</p><p>I enjoyed being an assistant principal. I loved learning under people I respected. I wanted more years making mistakes while someone wiser than me still occupied the chair. I wanted more afternoons around the milk crate. More conversations. More opportunities to quietly observe. More years learning before the final responsibility became mine. And if I&#8217;m truly honest with myself, I was completely comfortable and confident in that role. </p><p>But leadership has a way of arriving before we ever feel completely ready.</p><p>Circumstances changed. Leadership transitions happened. Responsibilities grew. Trusted voices encouraged me toward opportunities I wasn&#8217;t actively pursuing. Eventually, though not immediately, I found myself sitting in a chair I had spent years admiring from a distance.</p><p>Yet almost immediately, I began understanding how little I had actually understood.</p><p>The chair hadn&#8217;t changed. I had.</p><p>The conversations felt different when I was responsible for the outcome. The decisions felt heavier when my name was attached to them. The victories became sweeter because I now understood what they had cost. The disappointments lingered longer because there was no longer someone else&#8217;s shoulders carrying the final responsibility.</p><p>For the first time, I began understanding what those leaders around the milk crate had quietly protected me from:</p><p>They hadn&#8217;t hidden leadership from me. They had simply carried it so well that I only saw its visible side.</p><p>There are lessons that can be explained. There are lessons that can be observed. And then there are lessons that only reveal themselves once the weight becomes yours to carry.</p><p>That realization has stayed with me every day since.</p><h2>Let&#8217;s Sit With That for a Moment</h2><p>There is something about leadership that I think we have quietly misunderstood:</p><p>Somewhere along the way, we&#8217;ve begun talking about leadership almost entirely as though it were a destination.</p><p><em>Become</em> a principal. <em>Become</em> a superintendent. <em>Become</em> a director. <em>Become</em> a CEO. <em>Become</em> the leader.</p><p>Notice how often we describe leadership using nouns.</p><p>Titles. Positions. Offices. Chairs.</p><p>But leadership has never primarily been a noun. Leadership is a verb.</p><p>It is <em>serving</em> when service is inconvenient. It is <em>sacrificing</em> when no one notices. It is <em>protecting</em> people who may never know what you protected them from. It is <em>correcting</em> because you care-not because you enjoy confrontation.</p><p>It is <em>choosing</em> what is right over what is popular. It is <em>investing</em> in people who may one day surpass you. It is <em>carrying</em> responsibility on behalf of others. The chair simply gives those verbs a different address.</p><p><strong>Leadership is not a noun. Leadership is a verb.</strong></p><p>That&#8217;s why titles change so little.</p><p>The chair does not suddenly make someone humble. Or courageous. Or disciplined. Or compassionate.</p><p>It simply magnifies whatever has already been forming inside them.</p><p>That, I believe, is why leadership often surprises us.</p><p>We think the chair will change us. More often than not, the chair simply reveals us.</p><p>It reveals our habits. Our convictions. Our insecurities. Our character. Our preparation. Or our lack of it. And perhaps that is why the best leaders I have known never seemed obsessed with obtaining the chair. They were too busy becoming the kind of people capable of carrying it well.</p><p>This is essential in <em>formation</em> because there are sacrifices attached to leadership that no interview committee discusses. No certification program can fully prepare you for them. Leadership follows you home. Leadership sits with you at dinner. Leadership wakes you up at two in the morning replaying conversations from the day before. Leadership teaches you that vacations are rarely complete vacations. Leadership introduces a kind of loneliness that isn&#8217;t created by isolation but by responsibility.</p><p>I don&#8217;t say that to discourage anyone from leadership. I say it because someone once loved me enough to let me discover the truth instead of selling me the title.</p><p>Leadership isn&#8217;t simply something we <em><strong>do</strong></em>. Eventually, it becomes something we <em><strong>carry</strong></em>.</p><p>Maybe that&#8217;s the conversation we&#8217;ve been missing. Because if leadership is formed long before the title arrives, then perhaps preparation has far less to do with getting the job and far more to do with becoming the person the responsibility deserves.</p><h2>The Responsibility We Share</h2><p>If what we&#8217;ve reflected on so far is true, then I think it leaves all of us with a responsibility:</p><p>It would be easy to conclude that leadership development belongs to universities, certification programs, school districts, or organizations. Certainly, each of those plays an important role. We need strong preparation programs. We need thoughtful mentorship. We need systems that identify and develop future leaders.</p><p>But I don&#8217;t believe leadership formation has ever belonged exclusively to institutions. It has always belonged to people.</p><p>Long before there were graduate programs, there were apprentices. Long before there were leadership academies, there were seasoned leaders willing to let someone walk beside them. Long before there were certifications, there were conversations.</p><p>Someone opened a door. Someone stayed after the meeting. Someone explained not only <em>what</em> they had decided, but <em>why</em> they had decided it. Someone allowed another person to see the work behind the work.</p><p>That responsibility still belongs to us.</p><p>And if I&#8217;m honest, I worry that we&#8217;ve unintentionally created a culture that celebrates ambition before mastery. Confidence before competence. Certification before apprenticeship. Visibility before preparation.</p><p>Please don&#8217;t misunderstand me. Education matters. Degrees matter. Professional learning matters. Preparation matters. This isn&#8217;t an argument against any of those things. It is an argument for something deeper-</p><p><em>Character. Formation. Stewardship.</em></p><p>Because I&#8217;ve known leaders with impressive r&#233;sum&#233;s who struggled to steward people well. And I&#8217;ve known quiet, sometimes overlooked, professionals who possessed remarkable wisdom simply because they had faithfully mastered the work in front of them long before anyone handed them a title.</p><p>Perhaps the greatest danger isn&#8217;t that people aspire to leadership. We need aspiring leaders. </p><p>The danger is when we mistake being selected for being prepared. Those are not the same thing. The interview may open the door. The title may assign responsibility.But neither can substitute for the formation that should have already been taking place long before either one arrived.</p><p>Perhaps nowhere is this more consequential than education. Poor leadership decisions don&#8217;t simply affect organizations. They affect children. And children don&#8217;t get those years back. They don&#8217;t get fourth grade back. They don&#8217;t get eighth grade back. They don&#8217;t get senior year back.</p><p>Over the years, I&#8217;ve watched people pursue leadership for many different reasons. Some wanted greater influence. Some wanted new challenges. Some wanted higher salaries. Some wanted recognition. Some simply wanted to leave the classroom. Others believed their years of service alone entitled them to the next opportunity. Some of those motivations become dangerous when they become bigger than the desire to faithfully steward people (that&#8217;s another milk crate conversation for another day).</p><p>Leadership is most dangerous not only when the wrong people pursue it. It is dangerous when well-intentioned people inherit responsibility they were never truly prepared to carry. </p><p><strong>That reality ought to humble every one of us entrusted with leading schools and remind us that formation is a responsibility that belongs to all of us.</strong></p><p>If you&#8217;re already sitting in the chair, someone is learning leadership simply by watching you. Whether you intend to teach them or not.</p><ul><li><p>They&#8217;re watching how you respond when you&#8217;re criticized.</p></li><li><p>They&#8217;re watching how you treat people who disagree with you.</p></li><li><p>They&#8217;re watching whether you protect children or protect comfort.</p></li><li><p>They&#8217;re watching how you admit mistakes.</p></li><li><p>They&#8217;re watching how you celebrate others.</p></li><li><p>They&#8217;re watching whether your leadership is rooted in service or status.</p></li></ul><p>Conversely, if you&#8217;re standing beside the chair, don&#8217;t spend your days only asking how to get there. Ask how to become worthy of carrying it.</p><ul><li><p>Volunteer for difficult work.</p></li><li><p>Ask thoughtful questions.</p></li><li><p>Seek opportunities to learn the work no one applauds.</p></li><li><p>Find leaders who challenge your thinking more than they affirm your ambitions.</p></li></ul><p>Leadership has never been passed from one title to another. It has always been entrusted from one steward to another.</p><p>That responsibility belongs to all of us.</p><h2>The Heart of the Lesson</h2><p>For years, I admired the chair from a distance. Then one day, I sat in it.</p><p>The chair had not changed. I had.</p><p>What once looked like authority became stewardship. What once looked like recognition became responsibility. What once looked like influence became sacrifice. What once looked manageable revealed a weight I had never fully appreciated because extraordinary leaders had quietly carried it before me.</p><p>The better someone carries the burden, the less visible the burden becomes.</p><p>I understand now why the leaders who shaped me made leadership look so natural. It was never easy. They were simply carrying it well. And sitting here today, I realize something I could never have understood while standing beside them.</p><p>The chair was always bigger than I thought.</p><p>Truthfully, it still is.</p><h2>The Commission</h2><h3><em>For Those Already Sitting in the Chair</em></h3><p>If you&#8217;re already entrusted with leadership, I want to encourage you to do something that many of my mentors quietly did for me.</p><p>Invite someone closer. Don&#8217;t simply let them see the polished moments. Let them see the thinking behind difficult decisions. Explain the &#8220;why.&#8221; Allow them to observe the conversations that shape the outcome-not because they need another meeting to attend, but because they need formation more than information.</p><p>Let them watch you wrestle with competing priorities. Let them hear you admit when you don&#8217;t have all the answers. Let them see that leadership isn&#8217;t pretending to be certain. It&#8217;s faithfully stewarding responsibility, even when certainty is impossible.</p><p>One day someone else will sit where you now sit. Let&#8217;s leave them more prepared than we were.</p><h3><em>For Those Standing Beside the Chair</em></h3><p>If you&#8217;re hoping to lead someday, resist the temptation to chase the title before mastering the work.</p><p>Become excellent where you already are. Be dependable. Be teachable. Ask to learn. Ask to help. Ask to understand.</p><p>Don&#8217;t simply study leadership. Study leaders. Watch how they think. Watch how they respond. Watch what they protect. Watch what they refuse to compromise.</p><p>Most importantly, don&#8217;t confuse visibility with preparation.</p><p>The chair will eventually reveal whatever has been forming inside you all along. Spend this season becoming the kind of person the responsibility deserves.</p><h2>Reflection for the Week</h2><p>As I sat down to write this first reflection, I realized these questions were first for me before they were ever for anyone else.</p><p>Perhaps they&#8217;ll serve you as they&#8217;ve continued to serve me.</p><ul><li><p>Have I spent more time preparing for opportunities than preparing my character?</p></li><li><p>Am I mastering the responsibility already entrusted to me, or am I distracted by the responsibility I hope to receive next?</p></li><li><p>When I think about the leaders who&#8217;ve shaped my life, what burdens were they quietly carrying that I never stopped to appreciate?</p></li><li><p>If leadership found me tomorrow, what parts of my character would it magnify?</p></li><li><p>Am I becoming the kind of person people can trust with greater responsibility, even if no new title ever comes?</p></li><li><p>Finally, am I preparing to sit in the chair or preparing to carry its weight?</p></li></ul><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2>Recognition</h2><p>As this new journey begins, I find myself especially grateful for <a href="https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters">the people </a>who unknowingly shaped my understanding of leadership long before I was capable of fully appreciating it.</p><p>They never sat me down and handed me a blueprint for leadership.</p><p>They did something much more valuable. They let me watch. They trusted me enough to stand close. They invited me into conversations. They exposed me to the work behind the work. And perhaps most importantly, they quietly carried burdens I wasn&#8217;t yet ready to understand.</p><p>Looking back now, I realize those afternoons around an upside-down milk crate were never simply conversations after work. They were an apprenticeship. I just didn&#8217;t know it yet.</p><p>If I carry this chair with any measure of wisdom today, it is because others carried theirs with integrity long before I ever occupied one.</p><p>For that, I will always be grateful.</p><h2>Before Next Saturday</h2><p>Before next Saturday, I want to leave you with one simple challenge::</p><p><strong>If you&#8217;re already sitting in the chair</strong>, intentionally invite someone into a part of your work they wouldn&#8217;t normally see. Explain your thinking. Let them observe not only the decision, but the stewardship behind it.</p><p><strong>If you&#8217;re standing beside the chair</strong>, find a leader you genuinely respect and ask to learn-not because you&#8217;re chasing the next title, but because you&#8217;re committed to becoming the kind of leader others can trust when your opportunity comes.</p><p>Leadership has always been more than a position. It has always been a calling to steward people well.</p><p>Next week, we&#8217;ll explore one of the simplest yet most profound leadership lessons I ever received-a lesson from Doc that has echoed through every season of my career since.</p><p>She would often remind me:</p><div class="callout-block" data-callout="true"><p><strong>&#8220;You interview every day for the job you don&#8217;t even know you want.&#8221;</strong></p></div><p>At the time, I thought she was talking about professionalism. Years later, I realized she was talking about formation.</p><p>We&#8217;ll sit with that together next Saturday. Until then, pull up a milk crate. Find a quiet place to reflect. And ask yourself not what chair you&#8217;re hoping to sit in next but who you&#8217;re becoming before you ever get there.</p><p>Because wanting leadership and being prepared for leadership have never been the same thing.</p><p><strong>And that matters more than we know.</strong></p>]]></content:encoded></item><item><title><![CDATA[When the Door Finally Opens]]></title><description><![CDATA[Why Arrival Is Often Only the Beginning]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/when-the-door-finally-opens</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/when-the-door-finally-opens</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Thu, 02 Jul 2026 01:25:14 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/363f91da-a27d-40e8-8a1a-d39b0b2b1c34_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Over the past year of writing these <a href="https://lessonsfromthemilkcrate.substack.com/">milk crate </a>reflections, I have found myself increasingly aware of something I perhaps understood long before I had words for it:</p><p>Some of life&#8217;s greatest lessons begin teaching us quietly long before we fully recognize what we are learning.</p><p>Sometimes those lessons come during difficult seasons. Sometimes they come through people who see something in us that we have not yet learned to see in ourselves. And sometimes, they arrive on days like today.</p><p>July first.</p><p>For many people across education and countless other professions, today marks the beginning of something new.</p><p>New opportunities. New responsibilities. New teams. New offices. New chapters in careers that, for many, have taken years of preparation, sacrifice, and quiet perseverance to reach.</p><p>And I think there is something profoundly beautiful about that.</p><p>Because days like today remind us that sometimes the opportunities we step into publicly are often the result of years spent growing privately.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!r8Pm!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!r8Pm!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!r8Pm!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!r8Pm!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!r8Pm!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!r8Pm!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg" width="1024" height="1024" 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srcset="https://substackcdn.com/image/fetch/$s_!r8Pm!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!r8Pm!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!r8Pm!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!r8Pm!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb1837fc2-f03f-496e-b677-fb9c635cfb2b_1024x1024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>What This Week Understands</strong></h3><p>This week is not about questioning whether people are ready for leadership.</p><p>In fact, quite the opposite-today deserves celebration.</p><p>Across schools, organizations, churches, businesses, and communities everywhere, men and women are stepping into opportunities they have worked incredibly hard to earn.</p><p>For many, this moment represents years (sometimes decades) of preparation that few others ever truly saw.</p><p>Long nights. Professional sacrifice. Hard seasons. Quiet persistence. The kind of work that often happens far away from recognition.</p><p>And I think moments like this deserve our respect. Because for many, today is not simply the beginning of something new.</p><p>It is the culmination of years spent becoming the person someone believed was worthy of carrying new responsibility.</p><p>That matters. And it should be celebrated.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!JEMJ!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!JEMJ!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 424w, https://substackcdn.com/image/fetch/$s_!JEMJ!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 848w, https://substackcdn.com/image/fetch/$s_!JEMJ!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 1272w, https://substackcdn.com/image/fetch/$s_!JEMJ!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!JEMJ!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png" width="1456" height="971" 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srcset="https://substackcdn.com/image/fetch/$s_!JEMJ!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 424w, https://substackcdn.com/image/fetch/$s_!JEMJ!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 848w, https://substackcdn.com/image/fetch/$s_!JEMJ!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 1272w, https://substackcdn.com/image/fetch/$s_!JEMJ!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fcd432ef1-7b5e-4ba4-b4d0-63656f87e51c_1536x1024.png 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>A Lesson Learned Along the Way</strong></h3><p>One of the things leadership has slowly taught me over time is that preparation and responsibility often teach us entirely different lessons.</p><p>We spend years preparing ourselves for opportunities.</p><p>We pursue degrees. We complete certifications. We develop professionally. We learn how to interview well. We learn how to position ourselves for growth.</p><p>And all of that matters deeply.</p><p>But I have come to believe that many of us first encounter leadership as a <em><strong>noun</strong></em>.</p><p>A title. A position. A destination we hope to eventually reach.</p><p>But somewhere along the way we begin realizing leadership was never meant to remain a noun.</p><p>Because leadership, at its very core, is a <em><strong>verb</strong></em><strong>.</strong></p><p>It is lived long before it is given.</p><p>And often, the most important lessons about leadership begin teaching us long before anyone ever places responsibility in our hands.</p><h3><strong>The Weight I Understand Now</strong></h3><p>What fascinates me about leadership is that no amount of preparation can fully teach us what leadership will feel like once responsibility finally becomes ours.</p><p>We can spend years learning how to prepare for opportunity.</p><p>But opportunity itself often begins teaching entirely new lessons the moment it arrives. Because eventually leadership stops being about what we hoped to gain from it and begins becoming about what others now need from us.</p><p>This is why I have come to believe so deeply that leadership cannot simply be viewed as a title. Titles are nouns.</p><p>Leadership is action. Leadership is sacrifice. Leadership is stewardship. Leadership is waking up each day understanding that people now depend on the quality of your decisions.</p><p>And that reality humbles all of us.</p><p>Even those who have prepared themselves well.</p><h3><strong>The Heart of the Lesson</strong></h3><p>Perhaps that is what makes leadership such sacred work.</p><p>The day we finally arrive somewhere new is often the very day we begin discovering how much there still is left to learn.</p><p>Not because we were unprepared. Not because we are incapable. But because some lessons simply cannot be taught until responsibility finally becomes ours.</p><p>I think one of the great realizations leaders eventually discover is this:</p><p>Leadership was never about arriving. It was never simply about the title. It was never about finally reaching some destination we worked so hard to attain.</p><p>Leadership remains a daily act of service.</p><p>A commitment renewed every day through humility, sacrifice, discipline, reflection, and stewardship.</p><p>And perhaps the most beautiful part of leadership is recognizing that even after years of preparation the learning never truly stops.</p><h3><strong>What This Means For Us</strong></h3><p>Today, we celebrate those beginning new journeys.</p><p>We celebrate those stepping courageously into new responsibilities. We celebrate those who spent years quietly preparing for opportunities they hoped would one day come. And we celebrate the fact that for so many people, today represents the fulfillment of prayers they have likely carried for a very long time.</p><p>But I also think days like today remind all of us of something worth carrying forward:</p><p>Leadership is never a destination. It is never something we simply achieve and possess.</p><p>For many stepping into new opportunities today, the journey is not ending. In many ways, it is just beginning. Because leadership asks something beautiful of us:</p><p><em><strong>It asks us to become better tomorrow than we were yesterday for the sake of the people who now depend on us.</strong></em></p><p>And that is sacred work.</p><h3><strong>Reflection for the Week</strong></h3><p>As we reflect on the significance of days like today, let&#8217;s commit to sit with a few thoughts worth carrying forward this week.</p><ul><li><p>What seasons of preparation in my own life have quietly shaped me for responsibilities I did not yet know were coming?</p></li><li><p>How can I approach new opportunities with both confidence in what I know and humility about what I still have left to learn?</p></li><li><p>Who helped prepare me for the responsibilities I now carry, and how can I honor their investment through the way I lead others?</p></li><li><p>How do I remind myself that leadership is not found in the title itself, but in the daily work of serving people well?</p></li><li><p>How can I embrace every opportunity I receive not as an arrival point but as the beginning of continued growth and new responsibility?</p></li></ul><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h3><strong>Recognition</strong></h3><p>To those beginning new journeys today, congratulations.</p><p>Someone saw enough in your work, your preparation, your growth, and your potential to entrust you with something meaningful. Carry it well.</p><p>And remember that no degree, certification, interview, or professional accomplishment can fully prepare us for every lesson leadership begins teaching once responsibility finally belongs to us.</p><p>This Saturday at 10, we begin a new journey together <a href="https://bit.ly/4eUHsg7">here</a>.</p><div class="callout-block" data-callout="true"><p style="text-align: center;"><strong>Before You Sit In The Chair</strong><br><em>Why Leadership Is Bigger Than You Think</em></p></div><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!iUpk!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!iUpk!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!iUpk!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!iUpk!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!iUpk!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!iUpk!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg" width="1122" height="1402" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1402,&quot;width&quot;:1122,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:109795,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/204555205?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!iUpk!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!iUpk!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!iUpk!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!iUpk!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4249a480-5ff1-40ab-a8db-7b60582f0c1b_1122x1402.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Because sometimes we spend years preparing ourselves for an opportunity only to discover that the journey of leadership continues long after the opportunity finally arrives.</p><p>Because leadership was never meant to be a noun we chase, it was always meant to be a verb we live.</p><p><strong>And that matters more than we know.</strong></p>]]></content:encoded></item><item><title><![CDATA[Why The Milk Crate Still Matters]]></title><description><![CDATA[Six Months Later, Returning to Sacred Ground]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/why-the-milk-crate-still-matters</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 27 Jun 2026 14:02:24 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!A6vv!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Six months ago, on a quiet Saturday morning much like this one, I found myself writing about something most people would never give a second thought: <a href="https://lessonsfromthemilkcrate.substack.com/">an old milk crate</a>.</p><p>Now honestly, there is nothing particularly inspirational about a milk crate. It is not the kind of object anyone imagines carrying symbolic meaning. You do not frame it and hang it on the wall. You certainly do not imagine it becoming the foundation for a body of writing that would slowly begin connecting with people week after week.</p><p>And yet, somehow, here we are.</p><p>What began as a simple reflection about leadership, memory, and an old plastic crate sitting near the cafeteria loading dock on a school bus yard has quietly become something far more meaningful than I originally intended.</p><p>Every Saturday morning for the last six months, many of you have chosen to pull up a crate beside me. Together, we have reflected on leadership, sacrifice, family, grief, legacy, responsibility, purpose, integrity, and all of those quiet lessons life teaches us when we finally slow down long enough to listen.</p><p>And somewhere over these past six months, I have come to understand something I did not fully grasp when I wrote that very first reflection.</p><p>The milk crate was never the story-the people sitting around it were.</p><p>And before we begin the next chapter together next week, I believe it is only right that we return to where this journey first began.</p><p>Because before we move forward,, sometimes we owe it to ourselves to remember what first built us.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!A6vv!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!A6vv!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!A6vv!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!A6vv!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!A6vv!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!A6vv!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:234022,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/202335292?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!A6vv!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!A6vv!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!A6vv!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!A6vv!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F11cb57ac-daa7-4269-ab0c-f4f730f1b868_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>Disclaimer: What This Week Is Not</h2><p>Now before we go much further, I think it is important to be clear about something.</p><p>This week is not simply nostalgia for nostalgia&#8217;s sake. It is not a celebration of six months of writing. And perhaps most importantly-this reflection is not about me.</p><p>The older I become, the more uncomfortable I grow with society&#8217;s obsession with celebrating individual accomplishment as though any of us arrive at success independently.</p><p>We applaud promotions. We celebrate titles. We recognize awards. We elevate people who appear successful.</p><p>And yet we rarely pause long enough to acknowledge the invisible fingerprints left behind by those who shaped us long before anyone knew our names.</p><p>I find that troubling. Because I have yet to meet a truly exceptional leader who became exceptional alone.</p><p>Someone always came before them. Someone corrected them. Someone challenged them. Someone invested enough belief in them long before there was evidence that investment would pay off.</p><p>And if I have learned anything these last several years, it is this: whatever good exists within me, much of it belongs to someone else first.</p><p>This week is about remembering those people.</p><p>Because none of us arrive anywhere alone.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!csne!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffdc766be-c08f-4061-89c7-5fce847c653a_2000x1392.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!csne!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffdc766be-c08f-4061-89c7-5fce847c653a_2000x1392.png 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srcset="https://substackcdn.com/image/fetch/$s_!csne!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffdc766be-c08f-4061-89c7-5fce847c653a_2000x1392.png 424w, https://substackcdn.com/image/fetch/$s_!csne!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffdc766be-c08f-4061-89c7-5fce847c653a_2000x1392.png 848w, https://substackcdn.com/image/fetch/$s_!csne!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffdc766be-c08f-4061-89c7-5fce847c653a_2000x1392.png 1272w, https://substackcdn.com/image/fetch/$s_!csne!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffdc766be-c08f-4061-89c7-5fce847c653a_2000x1392.png 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>The Story We Need to Start With</h2><p>I still laugh when I think about that old milk crate.</p><p>It was faded. A little cracked. Sometimes stacked on top of another one because after walking twenty-five thousand steps inside a school building all day, nobody particularly wanted to bend too far just to sit down.</p><p>Hardly what anyone would picture when imagining leadership development.</p><p>There were no conference rooms. No professional development sessions. No strategic planning retreats. No polished presentations. No carefully curated leadership seminars.</p><p>Just exhausted administrators surviving another impossibly long day.</p><p>School had technically ended hours earlier. But buses (as they often did in those years) were running hopelessly behind schedule-past dinner time. The football team might already be heading to the locker room after practice. Someone was locking up the gym. The radio clipped awkwardly on my belt had long since stopped holding a charge. Dress shirts were wrinkled. Feet ached. Everyone was tired.</p><p>And somehow in the middle of that exhaustion, we found ourselves drifting toward the cafeteria loading dock near the bus yard.</p><p>No agenda. No formal meeting. No pretending to be anything other than tired human beings trying to survive a difficult profession.</p><p>And there sat those crates.</p><p>Some evenings we laughed until our stomachs hurt. Some evenings we vented about the impossible things leadership had asked of us that day. Some evenings someone told a story that would stay with me for years. And some evenings we sat completely silent. But not alone.</p><p>Yet somehow, even in silence-I was learning.</p><p>Looking back now, I understand that some of life&#8217;s greatest lessons never arrive in formal settings.</p><p>Leadership formation rarely happens in polished environments. Sometimes wisdom shows up in ordinary places long before we recognize how deeply those moments are shaping us.</p><p>That crate was never furniture.</p><p>It was sacred ground.</p><h2>Lessons From the Milk Crate</h2><p>Long before anyone ever entrusted me with an opportunity to lead, I had the extraordinary privilege of being surrounded by extraordinary leaders.</p><p>And I say privilege intentionally because now that I have lived long enough to lead on my own I realize just how rare that experience truly was.</p><p>I think often of those voices. I hear them even now.</p><p><em><strong>Doc.</strong></em></p><p>There are very few people in life I can honestly say changed the trajectory of who I would become.</p><p>She is one of them-the woman who hired a young teacher who thought he understood far more than he actually did. The woman who extended grace in moments where youthful arrogance probably should have cost me dearly. The woman who taught me that leadership means standing firmly between children and everything that threatens what they deserve. The woman who showed me what fearless leadership looks like when standards are non-negotiable and children remain the center of every decision.</p><p>She taught me that leadership is not popularity.</p><p>It is stewardship.</p><p><em><strong>S.W.</strong></em></p><p>Calm where others were emotional. Measured where others were reactive.</p><p>The man who taught me that leadership often requires quiet strength more than loud authority. The man who showed me how to remain steady when conflict arrives. Who taught me that doing right by children matters more than public perception.</p><p>He taught me professionalism. Presence. Dignity.</p><p>How to walk softly while carrying conviction strong enough to stand against pressure.</p><p><em><strong>Bert.</strong></em></p><p>Relentless in pursuit of excellence. Never satisfied with surface level understanding.</p><p>Always learning. Always growing. Always pushing people beyond their comfort zones.</p><p>She taught me that excellence is never accidental. That mastery of our craft requires constant refinement.</p><p>And perhaps most importantly that growth is not optional.</p><p><em><strong>D.W.</strong></em></p><p>The relationship builder.</p><p>The reminder that systems, policies, procedures, and organizational structures only work when trust exists first.</p><p>He taught me the value of people. The importance of presence. And that leadership is often measured less by what you enforce and more by whether people believe you genuinely care for them.</p><p><em><strong>Rose.</strong></em></p><p>Precision. Structure. Order.</p><p>The reminder that compassion without standards eventually harms everyone.</p><p>She taught me that some aspects of leadership demand rigidity. That legal responsibilities, accountability, and organizational excellence require discipline.</p><p>And sometimes love requires firmness.</p><p><em><strong>Dwayne.</strong></em></p><p>Joy. Humor. Humanity.</p><p>The reminder that serious work does not mean we must lose ourselves in seriousness. He taught me that leadership is not meant to consume every ounce of joy within us.</p><p>That laughter is necessary.</p><p>That the work is serious but we do not always have to take ourselves so seriously.</p><p><em><strong>Jermaine.</strong></em></p><p>Brotherhood. Proof that leadership does not have to be lonely. The reminder that some of our deepest friendships are born through shared responsibility and shared sacrifice.</p><p>He taught me that sometimes leadership places people in our lives who walk alongside us in seasons of growth neither of us fully understands at the time.</p><p><em><strong>Fred.</strong></em></p><p>Strength through suffering. A man who understood grief in ways most people never will. Yet somehow still showed up every single day committed to protecting children and helping guide them toward better decisions.</p><p>He taught me that loving children sometimes requires being hard enough to save them from themselves. And that accountability and compassion are not opposites. Sometimes one exists because of the other.</p><p>These people shaped me and I carry pieces of all of them into every decision I make today.</p><h2>The Collision</h2><p>And perhaps this is where I find myself increasingly concerned with modern leadership. Because somewhere along the way I fear we stopped valuing formation and started worshipping elevation.</p><p>We have become obsessed with certifications. Titles. Promotions. Status. Recognition. Visibility.</p><p>We teach people how to interview. We teach people how to answer hypothetical leadership questions. We teach people how to collect credentials. We teach people how to pursue advancement.</p><p>But I wonder sometimes have we stopped teaching people how to become worthy of leadership itself?</p><p>Because leadership is not learned through PowerPoint presentations. It is not developed through collecting graduate degrees. You can&#8217;t social media like, post or share your way into it. And it is not earned simply because someone survived a certification program.</p><p>Leadership is formed through observation. Humility. Failure. Sacrifice. Consistency. Watching extraordinary people quietly do difficult work long enough that their habits slowly become our habits.</p><p>The world teaches people to chase titles. The milk crate taught us to chase wisdom.</p><p>And there is a tremendous difference between the two.</p><h2>The Weight I Understand Now</h2><p>There is a strange thing that happens as we grow older in leadership: the people we once admired slowly begin making more sense to us. </p><p>When we are young in this work, we often see only the parts of leadership that are visible. We notice the confidence. We notice the decision-making. We notice the authority. We notice the outcomes. </p><p>But time has a way of teaching us what observation alone never could. Because eventually, if we stay in the work long enough, we begin carrying weight of our own. And suddenly, the people who once seemed larger than life begin to look different. Not smaller. But somehow greater. Because now we understand what they were carrying all along. </p><p>I understand Doc differently now. When I first worked under her, I saw fearlessness. I saw decisiveness. I saw impossibly high standards and a woman who never seemed shaken no matter how difficult the conflict standing before her. What I could not see then was the emotional weight she was carrying every single day trying to protect an entire school community while shielding those of us under her from burdens we were not yet prepared to carry ourselves. </p><p>Now I understand why she stood so firmly-because children needed someone willing to stand between them and everything working against their future. </p><p>I understand S.W. differently now. At the time, I simply admired how calm he always remained. Nothing seemed to shake him. Angry parents. Conflict. Crisis. Difficult conversations. He never moved emotionally. What I did not understand then was how much discipline it takes to constantly choose professionalism over reaction. </p><p>I understand now that his calmness was not personality-it was discipline. It was restraint. It was a daily commitment to doing what was right rather than what was emotionally satisfying. </p><p>I understand Bert differently now. At times, I thought her relentless pursuit of instructional excellence felt exhausting. She pushed constantly. Always refining. Always asking more. Always demanding deeper thought. What I failed to appreciate then was that excellence is not accidental.</p><p>She understood something I understand much better now: children cannot afford adults who become comfortable. The moment educators stop learning, children begin losing opportunities they can never recover. </p><p>I understand D.W. differently now. There were moments I questioned whether relationships could truly solve as much as he believed they could. I sometimes found myself leaning more heavily toward accountability than connection. </p><p>But now I understand something he knew better than I did then: People do not follow systems, people follow trust. And sometimes leadership requires slowing down long enough to see the humanity sitting in front of you before rushing toward correction. </p><p>I understand Rose differently now. I saw her precision. I saw her structure. I saw the rigidity she brought to systems that required absolute attention to detail. </p><p>But now I understand that some responsibilities simply do not allow flexibility. Leadership sometimes requires carrying burdens where one overlooked detail can create consequences for countless others. She taught me something I now live every day. Standards matter most in the places where mistakes carry the greatest cost. </p><p>I understand Dwayne differently now. At the time, I simply appreciated the laughter he brought into hard days. He knew how to make difficult work feel lighter. He reminded us not to take ourselves too seriously. </p><p>But I now recognize something deeper-joy is not separate from leadership. It sustains leadership. Because no one can carry serious work forever without moments that remind them they are still human. </p><p>I understand Jermaine differently now. At the time, I simply appreciated partnership. Shared responsibility. Brotherhood. The comfort of knowing difficult work did not have to be carried alone. </p><p>But now I understand how rare it is to find people who are willing to carry weight alongside you without competing with you. Leadership can become incredibly lonely and I understand now why having someone beside you who shares the burden matters more than titles ever will. </p><p>I understand Fred differently now. I watched him hold children accountable with remarkable firmness while somehow still caring deeply for them. At times I simply admired his toughness. </p><p>But now I understand that what I was witnessing was love. Real love. The kind of love that understands consequences today may save someone from destruction tomorrow. He understood better than most of us that protecting children does not always look gentle. Sometimes the deepest form of care is refusing to excuse behavior that will one day destroy them. </p><blockquote><p><strong>So perhaps that is what growing older in leadership teaches us most: the people who shaped us were often carrying burdens we could not yet recognize. </strong></p></blockquote><p>They were shielding us. Absorbing pressure. Sacrificing pieces of themselves so we could grow without carrying weight we were not yet ready to understand. </p><p>Now as I sit in a chair heavy and large enough to understand some of those same burdens, I find myself humbled. Because I realize now that much of what made these people extraordinary had very little to do with what they accomplished publicly. Their greatness was not in what they did. It was in what they quietly carried for others. </p><p>And perhaps the strangest realization of all is this:</p><div class="callout-block" data-callout="true"><p>I no longer admire them simply because of what they taught me. I admire them because now I understand what it cost them to teach it. </p></div><p>And I am forever grateful that before leadership ever formally belonged to me I had the privilege of learning from people strong enough to carry weight I could not yet see.</p><h2>The Heart of the Lesson</h2><p>Six months later, I finally understand something I could not fully articulate when I first began writing these reflections:</p><p>The milk crate was never simply a place where exhausted leaders sat down after difficult days.</p><p>It represented the place where leadership first found me long before leadership formally belonged to me. It taught me that leadership is stewardship. It taught me that sacrifice often precedes recognition. It taught me that wisdom is rarely loud. It taught me that no title can ever replace the discipline of listening long enough to learn. It taught me that leadership begins long before anyone hands us authority.</p><p>And perhaps most importantly it taught me that the people around us are quietly shaping who we are becoming whether we realize it or not.</p><p>Long before I ever sat in the principal&#8217;s chair I first sat on a faded old milk crate.</p><p>And I am better because I did.</p><h2>The Commission</h2><p>I have come to believe something deeply these last few years:</p><p>The greatest tragedy in leadership is not failure. It is forgetting the people who first prepared us to carry responsibility we had not yet imagined.</p><p>Every one of us is sitting in chairs today built by someone else&#8217;s sacrifice.</p><p>Someone taught us. Someone corrected us. Someone challenged us. Someone believed enough in us to invest before we had earned their confidence.</p><p>But eventually the responsibility shifts.</p><p>Because one day we become the people sitting around someone else&#8217;s milk crate. And what we pour into others will determine far more than anything we ever accomplish ourselves.</p><p>Leadership was never meant to end <em>with</em> us.</p><p>It was always meant to multiply <em>through</em> us.</p><h2>Reflection for the Week</h2><p>As I sit here six months into this writing journey, I find myself wrestling with a few questions.</p><ul><li><p>Who first shaped the professional standards I now carry with me every day?</p></li><li><p>Have I properly acknowledged those who invested in me before I understood their impact?</p></li><li><p>Am I spending enough time learning from those who have gone further than I have?</p></li><li><p>Have I become too focused on advancement instead of development?</p></li><li><p>Whose milk crate mentor am I becoming for someone else right now?</p></li></ul><p>And perhaps most importantly have I sat long enough to listen before trying to lead?</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong>A Continued Invitation</strong></h2><p><span>As we continue this journey, we invite you again to engage with our new devotional, </span><strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p><span>Take a moment this week to read, reflect, and share </span><a href="https://returningtothemilkcrate.substack.com/">here</a><span>.</span></p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h2>Recognition</h2><p>As I reflect on six months of these Saturday morning conversations I know these words have never truly belonged to me.</p><p>Every lesson I have shared first belonged to someone who invested in me long before I understood how deeply their wisdom would remain with me.</p><p>To Doc. To S.W. To Bert. To D.W. To Rose. To Dwayne. To Jermaine. To Fred.</p><p>Thank you. You are woven into every lesson I carry forward.</p><p>And to every reader who has joined me each week-thank you.</p><p>What began as a simple reflection has quietly become something much bigger than I ever intended.</p><p>And I am grateful for every person who has chosen to sit beside me here.</p><h2>Leave Something on the Crate</h2><p>Next week we begin a new journey together.</p><p>A new 8-week reflection series I have been carrying quietly for quite some time:</p><div class="callout-block" data-callout="true"><h5 style="text-align: center;"><em><strong>Before You Sit in the Chair: Why Leadership Is Bigger Than You Think.</strong></em></h5></div><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!7nEN!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!7nEN!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!7nEN!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!7nEN!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!7nEN!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!7nEN!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg" width="1122" height="1402" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/f10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1402,&quot;width&quot;:1122,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:109795,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/202335292?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!7nEN!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 424w, https://substackcdn.com/image/fetch/$s_!7nEN!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 848w, https://substackcdn.com/image/fetch/$s_!7nEN!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!7nEN!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff10a6f93-044d-439e-a9e4-4c281f9f83a0_1122x1402.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Together, we are going to wrestle with a truth I believe far too many people discover far too late:</p><p><strong>Everybody wants the chair. Very few people understand what sitting there will require them to surrender.</strong></p><p>So before we begin, take a moment this week.</p><p>Reach out to someone who helped shape you. Thank the people who invested in you before you understood what they were preparing you for. Become that voice for someone else.</p><p>Because I have learned something sitting around that old milk crate:</p><p>The quietest conversations, the smallest moments, and the people who choose to invest in us often shape the rest of our lives.</p><p>And I promise you this-</p><p><strong>It matters more than you know.</strong></p>]]></content:encoded></item><item><title><![CDATA[Long After We Leave the Room]]></title><description><![CDATA[Lessons from the Leaders Who Never Needed the Spotlight, Part V]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/long-after-we-leave-the-room</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/long-after-we-leave-the-room</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 20 Jun 2026 14:01:31 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/1fe7fd12-c560-4d1d-9d30-cbdfc716feff_1535x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<div class="pullquote"><h4><em>&#8220;Don&#8217;t try to fill my shoes. Fill your own. And that&#8217;s enough.&#8221; - &#8220;</em>Doc&#8221;</h4></div><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!_Vst!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!_Vst!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 424w, https://substackcdn.com/image/fetch/$s_!_Vst!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 848w, https://substackcdn.com/image/fetch/$s_!_Vst!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!_Vst!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!_Vst!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg" width="1080" height="1350" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1350,&quot;width&quot;:1080,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:584651,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/201895030?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!_Vst!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 424w, https://substackcdn.com/image/fetch/$s_!_Vst!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 848w, https://substackcdn.com/image/fetch/$s_!_Vst!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!_Vst!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F2c986f1c-cd9a-4747-95b5-64398b4f011c_1080x1350.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>The <a href="https://lessonsfromthemilkcrate.substack.com/p/lessons-from-the-milk-crate">milk crate</a> was never simply a place where stories were shared.</p><p>It was where wisdom slowed down long enough to be heard. A place where ordinary conversations somehow carried extraordinary lessons. Where laughter softened hard truths. Where life experience quietly taught lessons no textbook ever could. It was where people who had already carried life&#8217;s burdens sat long enough to help prepare those coming behind them to carry burdens of their own.</p><p>And perhaps that is what makes the milk crate the perfect place to end this journey through <em><a href="https://lessonsfromthemilkcrate.substack.com/p/the-legacy-you-leave-behind">Legacy: Lessons from the Leaders Who Never Needed the Spotlight.</a></em></p><p>For five weeks now, we have sat together reflecting on legacy.</p><p>Not the kind attached to plaques hanging on walls. Not the kind connected to promotions, titles, applause, recognition ceremonies, or carefully curated reputations.</p><p>But the kind of legacy quietly built through service.</p><p><a href="https://lessonsfromthemilkcrate.substack.com/p/the-legacy-you-leave-behind">Week One</a> reminded us that legacy is not something great leaders chase. The best leaders are too busy pursuing purpose to waste time pursuing remembrance.</p><p><a href="https://lessonsfromthemilkcrate.substack.com/p/the-things-we-leave-in-people">Week Two</a> forced us to confront the truth that legacy is not what we leave <em>for</em> people. It is what we leave <em>in</em> people. Confidence. Courage. Wisdom. Opportunity. Belief.</p><p><a href="https://lessonsfromthemilkcrate.substack.com/p/the-cost-of-legacy">Week Three</a> reminded us that meaningful legacy costs something. The sacrifices nobody applauds. The early mornings. The late nights. The burdens carried when nobody is watching.</p><p><a href="https://lessonsfromthemilkcrate.substack.com/p/legacies-to-carry-legacies-to-bury">Last week</a> we wrestled with one of the hardest truths of all: not everything inherited deserves continuation. Some lessons deserve carrying. Some patterns deserve burial. Wisdom should travel. Wounds should stop with us.</p><p>And now we arrive at the final lesson:</p><p style="text-align: center;"><strong>What remains long after we leave the room?</strong></p><p>The truth is somewhere over these last five weeks I realized this series was never really about legacy-it was gratitude disguised as reflection.</p><p>Because this month, two of my milk crate mentors - &#8220;Doc&#8221; and S.W. - enter retirement. And I found myself wrestling with something I do not think we acknowledge enough:   There is grief in transition.</p><p>There is grief when extraordinary leaders begin laying down burdens they have carried for decades. And perhaps one of the strangest parts of maturity is realizing something profoundly humbling -we rarely understand what others were carrying for us while they are carrying it.</p><p>Oftetimes, we only understand their sacrifices once we begin carrying burdens of our own.</p><p>Wisdom has a strange way of aging well. The older we become, the more expensive old lessons begin to look.</p><p>And perhaps that brings us to what this week understands.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!M8f6!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!M8f6!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!M8f6!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!M8f6!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!M8f6!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!M8f6!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:234022,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/201895030?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!M8f6!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!M8f6!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!M8f6!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!M8f6!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F883cd5c1-6a08-4f43-b1c7-36aae75e8e91_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>What This Week Understands</h2><p>We approach this week without a disclaimer. But with understanding.</p><p>This week understands grief. Not grief born from death. But grief born from transition.</p><p>A quiet grief. The kind that arrives when extraordinary people begin stepping away from spaces where we somehow convinced ourselves they would always remain.</p><p>There is a grief attached to watching good leaders leave that few people ever acknowledge.</p><p>Not because the work stops. The work continues. Schools continue. Organizations continue. Children still arrive every morning. Problems still demand solving. Meetings still happen. Responsibilities still exist.</p><p>The grief comes from realizing that the people who carried extraordinary burdens for years are no longer carrying them.</p><p>The office door that was always open. The seasoned voice in difficult moments. The person who quietly absorbed pressure so others could continue functioning. The leader who protected culture. Protected children. Protected people. Protected standards.</p><p>And then one day they begin stepping away.</p><p>And suddenly the room feels different before they have even left.</p><p>We grieve because something valuable existed. We do not grieve what did not matter.</p><p>But this week also understands something equally important: grief becomes dangerous when admiration turns passive.</p><p>We dishonor legacy when we spend more time missing great leaders than becoming responsible for what they prepared us to carry.</p><p>Because the greatest way to honor those who shaped us is not remembering them. It is continuing the work they spent decades preparing us to do.</p><p>And perhaps nowhere is that lesson more evident than in the giants who helped build us.</p><h2>The Giants Who Built Us</h2><p>There are leaders who improve organizations. Then there are rare leaders who permanently alter the trajectory of every life they encounter.</p><p>Those leaders become impossible to forget.</p><p>That is how I think about <em>Doc.</em></p><p>What made her extraordinary was never simply what she accomplished institutionally.</p><p>Plenty of leaders improve schools. Plenty of leaders improve outcomes. Plenty of leaders can point to successful metrics.</p><p>That was never what made her exceptional.</p><p>What made <em>Doc</em> unforgettable was that she understood leadership beyond outcomes. She understood stewardship of people. She believed deeply that leadership was never about collecting followers. Leadership was about building future leaders. And that is rare.</p><p>Because insecure leaders often fear strong people. Weak leaders hoard opportunity. Weak leaders protect visibility. Weak leaders become uncomfortable when those around them begin growing beyond their own limitations.</p><p>But strong leaders intentionally develop people capable of surpassing them.</p><p>And <em>Doc</em> never feared strong people. She created them.</p><p>She believed children belonged at the center of every decision. She believed leadership meant developing those entrusted to you. She believed responsibility extended far beyond your own position. She saw future leaders long before others recognized it themselves.</p><p>And she developed people fearlessly. Not because it benefited her. Because she understood stewardship.</p><p>And then there is <em>S.W.</em></p><p>Forty-six years. Can we sit with that for just a minute?</p><p>Because forty-six years is not longevity. Forty-six years is a covenant.</p><p>The truth is somewhere along the way I think I convinced myself men like him simply belonged in schools forever. Certain people become so woven into institutions that we stop imagining what those institutions look like without them.</p><p>You do not accidentally spend nearly half a century serving children.</p><p>Forty-six years means thousands of mornings choosing responsibility before comfort. Thousands of early arrivals. Thousands of late evenings. Thousands of athletic events. Thousands of weekends surrendered. Thousands of unseen sacrifices nobody applauded.</p><p>I watched him arrive before everyone else. Walking classrooms. Checking facilities. Preparing contingency plans. Making sure children entered spaces prepared to serve them well.</p><p>Then staying long after everyone else had gone home.</p><p>Long days. Long weeks. Long seasons.</p><p>But responsibility remained. And he honored it every single time.</p><p>Leadership was never something S.W. performed. Responsibility was simply his way of life.</p><p>And people like this do not retire quietly-they leave vacancies organizations often do not know how to measure.</p><p>And suddenly I realize something painful.</p><p>People like this are leaving the room. An era is ending.</p><p>And naturally, there is grief in that.</p><p>Not because the work stops.</p><p>Because we finally understand what they carried.</p><h2>The Final Gift Great Leaders Leave Behind</h2><p>For years I carried one lesson from Doc that I understand very differently now than when she first said it.</p><p>I remember her stopping me once and saying:</p><p><strong>&#8220;Stop trying to be me. I don&#8217;t need ten of me. I need you to be you. Don&#8217;t try to fill my shoes. Fill your own. And that&#8217;s enough.&#8221;</strong></p><p>At the time I thought it was humility. Years later I realize it was instruction.</p><p>Great leaders are not trying to create copies of themselves.</p><p>They are preparing successors. The shoes were never the point-the mission was.</p><p>Great leaders understand something insecure leaders never learn. Leadership is not proven by how indispensable you become. Leadership is proven by how prepared others are when you leave.</p><p>Doc was never preparing people to become Doc. S.W. was never sacrificing so people would admire his work ethic.</p><p>They were preparing others. Preparing <em>us.</em></p><p>And perhaps the greatest gift mentors leave behind is not memory. <em>I</em>t&#8217;s preparation.</p><p>And the greatest tribute we can offer is not admiration.It is stewardship.</p><p>Because admiration inspires.But sacrifice sustains.</p><p>And eventually admiration alone becomes insufficient.</p><h2>What This Means For Us</h2><p>And perhaps watching leaders like this step away has forced me to confront something increasingly uncomfortable.</p><p>I find myself looking around organizations everywhere and realizing that while one generation quietly lays down burdens they have carried faithfully for decades yet too often the generation coming behind them is far more interested in inheriting authority than understanding responsibility.</p><p>And that should concern all of us.</p><p>Because one of the greatest dangers facing organizations today is not poor leadership.</p><p>It is <strong>premature leadership.</strong></p><p>Too many people are pursuing seats they have done absolutely nothing to prepare themselves to occupy.</p><p>There are people who admire authority but have never studied burden. People who want leadership because titles make them feel important. People who pursue visibility because recognition satisfies ego. People who enjoy proximity to power but have absolutely no understanding of responsibility.</p><p>Organizations everywhere are suffering because of it.</p><p>Leadership is not romantic. Leadership is not exciting. Leadership is not a reward for ambition. Leadership is burden. Leadership is sacrifice. Leadership is accountability. Leadership is loneliness. Leadership is responsibility carried on behalf of others.</p><p>Far too many people admire leadership because they have only observed position. They have never studied burden.</p><p>And by the time people realize someone was unprepared, they are sometimes already sitting in the chair.</p><p>That should concern all of us.</p><h2>The Heart Of The Lesson</h2><p>Every day we leave something behind.</p><p>A habit. A standard. A fear. A courage. A wound. A kindness. An expectation. An example. And every day people are learning from how we lead.</p><p>Children are learning. Teachers are learning. Future leaders are learning.</p><p>They are watching how we respond under pressure. Watching how we treat people after promotion. Watching whether authority changed our humility. Watching what we tolerate. Watching what we celebrate. Watching what we quietly permit.</p><p>Because leadership is always teaching. Even when we do not realize we are teaching.</p><p>Perhaps one of the greatest misunderstandings about legacy is believing legacy begins at retirement. It does not.</p><p>Legacy begins the moment people start adjusting behavior because of our influence. Legacy begins the moment children begin believing in themselves because someone believed in them first. Legacy begins the moment culture shifts because someone had courage enough to protect what mattered.</p><p>Legacy is never created when we leave. Leaving simply reveals what we were building all along.</p><p>And the true measure of leadership is not whether people miss us when we are gone. It is whether people were stronger because we were there.</p><p>That is legacy.</p><h2>Reflection For The Week</h2><p>As we close this series, I find myself sitting with a few difficult questions.</p><ul><li><p>Who helped shape the leader I am becoming and have I truly honored what they poured into me?</p></li><li><p>Am I preparing myself for responsibility or simply admiring positions I have not yet earned?</p></li><li><p>If those who mentored me observed how I lead today, would they recognize their fingerprints in my work?</p></li><li><p>Have I confused ambition with readiness?</p></li><li><p>What burdens am I willing to carry for others long before anyone notices what I sacrifice?</p></li></ul><p>Because eventually our turn comes.</p><p>And when it does, preparation cannot begin that day.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2>Recognition</h2><p>This series on legacy was never simply writing. It was gratitude placed on paper.</p><p>It was my own quiet attempt to make sure two extraordinary people were honored while they could still hear how deeply their work mattered.</p><p><em><strong>Doc</strong>&#8230; thank you.</em></p><p>Thank you for showing me that leadership was never about standing in the spotlight. Thank you for putting children first without compromise. Thank you for fearlessly developing people. Thank you for teaching me that leadership means building future leaders.</p><p>And thank you for one lesson I suspect I will carry forever: </p><p><strong>&#8220;Don&#8217;t try to fill my shoes. Fill your own. And that&#8217;s enough.&#8221;</strong></p><p>I understand now what you were teaching me. You were never asking me to replace you. You were preparing me to carry responsibility myself.</p><p>And to my first partner, <em><strong>S.W. </strong></em>Forty-six years is more than a career. It is a life poured out in service. Thank you for showing what stewardship looks like. What discipline looks like. What consistency looks like. What responsibility looks like when honored every single day.</p><p>You both leave behind far more than memory. You leave behind standards. And perhaps that is why this month mattered so much to me. Because this five-week journey has quietly been my final act of gratitude.</p><p>Flowers should be given while extraordinary people can still smell them.</p><p>You both helped shape the leader so many of us continue becoming.</p><p>And for that, we thank you.</p><h2>The Final Lesson</h2><p>And perhaps that is the lesson I leave this series carrying most heavily:</p><p>The generation before us spent decades showing us what stewardship looks like. They taught us how to serve without applause. How to sacrifice without demanding recognition. How to carry responsibility long before anyone noticed the burden.</p><p>And now-whether we realize it or not-our turn is coming. Soon enough, someone will ask us to carry what others once carried for us.</p><p>The question is not whether we want leadership. The question is whether we have prepared ourselves to deserve it.</p><p>And perhaps that is exactly where our next conversation on the milk crate begins.</p><p>So in two weeks, we begin a new journey together&#8230;.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!fMvl!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!fMvl!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 424w, https://substackcdn.com/image/fetch/$s_!fMvl!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 848w, https://substackcdn.com/image/fetch/$s_!fMvl!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!fMvl!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!fMvl!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg" width="1080" height="1350" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/b11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1350,&quot;width&quot;:1080,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:511747,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/201895030?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!fMvl!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 424w, https://substackcdn.com/image/fetch/$s_!fMvl!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 848w, https://substackcdn.com/image/fetch/$s_!fMvl!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!fMvl!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fb11f3d37-8745-478e-8137-9e833650f749_1080x1350.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Because wanting leadership and being prepared for leadership have never been the same thing.</p><p><strong>And that matters more than we know.</strong></p>]]></content:encoded></item><item><title><![CDATA[Legacies to Carry, Legacies to Bury]]></title><description><![CDATA[Lessons from the Leaders Who Never Needed the Spotlight, Part IV]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/legacies-to-carry-legacies-to-bury</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/legacies-to-carry-legacies-to-bury</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 13 Jun 2026 14:01:35 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/0a194a4c-af9a-4553-bd45-8c34c65bd22f_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>The <a href="https://lessonsfromthemilkcrate.substack.com/p/lessons-from-the-milk-crate">milk crate</a> was never just a place where lessons were taught. It was also a place where lessons were tested.</p><p>Over the past several weeks, we have been sitting together on the milk crate reflecting on legacy-not as something we chase, but as something we leave behind through faithful service.</p><p>In <a href="https://lessonsfromthemilkcrate.substack.com/p/the-legacy-you-leave-behind">Week One</a>, we reflected on the truth that legacy is not something we pursue for ourselves. The best leaders are rarely the ones chasing recognition. More often, they are the ones quietly standing behind the spotlight while helping others shine.</p><p>In Week Two, we reflected on <em><a href="https://lessonsfromthemilkcrate.substack.com/p/the-things-we-leave-in-people">The Things We Leave in People</a></em>. We explored how meaningful legacy is found not in buildings named after us or plaques hanging on walls, but in the courage we build, the opportunities we create, and the lives we help shape.</p><p>Last week, we reflected on <em><a href="https://lessonsfromthemilkcrate.substack.com/p/the-cost-of-legacy">The Cost of Legacy</a></em>. We honored the sacrifices attached to meaningful influence-the early mornings, the late nights, the unseen preparation, and the consistency required to leave something worth leaving.</p><p>But this week brings us to perhaps the most difficult question of the entire series: Not everything we inherit deserves continuation. Not every lesson should travel. Not every tradition should survive another generation. Not every leadership pattern deserves preservation.</p><p>Because if legacy is what gets passed forward, then every leader eventually faces the same responsibility: <strong>What do I carry? And what do I bury?</strong></p><p>The milk crate taught us both. It taught us what to hold onto. And sometimes it taught us what to leave behind.</p><p>Because some people inherit titles. Others inherit wounds. And the wisest leaders learn the difference between the lessons they should carry and the lessons they should bury.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!wqlO!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!wqlO!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!wqlO!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!wqlO!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!wqlO!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!wqlO!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/201528214?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!wqlO!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!wqlO!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!wqlO!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!wqlO!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F143e1adf-03c9-448f-9c01-4f8d2ced1acd_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong>Disclaimer: What This Week Is Not</strong></h2><p>This week is not about blame. It is not about revisiting old wounds. It is not about criticizing former supervisors. And it is certainly not about complaining.</p><p>Because if we are not careful, we can become so focused on what happened to us that we lose sight of what is supposed to happen through us.</p><p>The truth is that every leader inherits something. Some inherit healthy cultures. Some inherit broken cultures. Some inherit extraordinary mentors. Some inherit difficult experiences. Some inherit encouragement. Some inherit criticism. Some inherit confidence. Some inherit insecurity.</p><p>And while we may not choose what we inherit, we are responsible for what we do with it.</p><p>That is why this week is not about blame. Because healing rarely begins with assigning fault. Healing begins with discernment. We cannot become the face of progress while remaining trapped inside the wound.</p><p>Nor is this week about criticizing the leaders who came before us. Leadership requires grace. Every leader has blind spots. Every leader has seasons of growth. Every leader makes mistakes. And if we are fortunate enough to lead long enough, we eventually discover that many of the decisions we once judged from a distance become far more complicated once we sit in the chair ourselves.</p><p>Yet grace does not require blindness. To grow, we must be willing to learn both what to do and what not to do. Some leaders teach us through their strengths. Others teach us through their shortcomings. Some seasons are filled with lessons we eagerly carry forward. Other seasons are filled with lessons we quietly bury. Both are valuable. Both shape us. And both become part of our leadership inheritance.</p><p>This week is also not about mere complaining. Complaining keeps us focused on the problem. Discernment helps us become part of the solution. Because not everything that was done before us should continue through us. Not every tradition deserves continuation. Not every pattern deserves preservation. Not every wound deserves another generation.</p><p>The question is not what happened. The question is what we choose to do with what happened.</p><p>And perhaps one of the earliest lessons I learned about carrying and improving what we inherit came from something far simpler than leadership.</p><p>It came from a peanut butter and jelly sandwich.</p><h2><strong>The &#8216;95 Peanut Butter and Jelly Conflict</strong></h2><p>When I was a child, a cousin came to visit and was introduced to what I still believe is the superior way to make a peanut butter and jelly sandwich: my mother would mix the peanut butter and jelly together in a bowl before spreading it on the bread. Simple. Effective. Life-changing. At least according to my cousin (although I agree). The sandwich was richer. Sweeter. More balanced. And apparently memorable enough that when he returned home, a minor family controversy followed.</p><p>Suddenly, the traditional method no longer measured up. Nor was he satisfied with the convenience of pre-mixed <em>Goober</em> by Smucker&#8217;s.</p><p>His mother jokingly accused my mother of being &#8220;extra.&#8221; To be fair, she is. And somehow the treats are always sweeter because of it.</p><p>As children, we thought the disagreement was about sandwiches. Looking back, I think it was really about inheritance. My mother did not throw away the sandwich. She<em> improved</em> the process. The bread remained. The peanut butter remained. The jelly remained. The foundation remained. She simply found a way to make it better.</p><p>And perhaps that is one of the most important lessons leadership ever teaches us: not all change requires destruction. Sometimes improvement honors what came before it. Sometimes stewardship means preserving the best parts while making room for growth. Sometimes leadership is not about replacing a tradition. It is about refining it.</p><p>And unfortunately, I later experienced a season that taught me the opposite lesson.</p><h2><strong>When Different Wasn&#8217;t Better</strong></h2><p>Several years later, I found myself working under a newer leader who inherited a remarkably healthy culture. The previous leader had built a strong foundation. The staff was well prepared. The culture was positive. People felt valued. Business was great. The organization was healthy. Yet almost immediately, the new leader became fixated on the comparison of their predecessor.</p><p>&#8220;We are like oil and water,&#8221; they would often say&#8230;&#8221;Anything she did, I&#8217;ll do the opposite.&#8221;</p><p>At first, those comments seemed harmless. Eventually, they became philosophy. And unfortunately, that philosophy was put into practice. It didn&#8217;t lead to a single success&#8230;</p><p>This reflection is not about that leader. Every leader deserves grace. Every leader deserves room to grow. Every leader learns difficult lessons along the way.</p><p>This reflection is about the season itself. Because that season taught me something I have never forgotten: Different is not automatically better. Sometimes leaders become so determined to establish their own identity that they reject wisdom simply because it belonged to someone else. They mistake contrast for progress. Opposition for innovation. Distance for leadership.</p><p>But healthy leadership is rarely found at either extreme. Healthy leadership requires discernment. The ability to recognize what deserves preservation. The humility to recognize what deserves improvement. And the courage to recognize what deserves retirement.</p><p>Looking back now, I realize that season taught me two equally important lessons.</p><p>Some seasons teach us what to do. Some seasons teach us what not to do.</p><p>Both have value. Both leave fingerprints. Both become part of our leadership inheritance. The responsibility is determining which lessons should continue traveling with us.</p><p>And years later, I found myself sitting in a leadership role where that very question became unavoidable.</p><h2><strong>The Loneliness of Discernment</strong></h2><p>One of the loneliest responsibilities in leadership is deciding what should survive you.</p><p>Not because leadership itself is lonely. But because discernment often is.</p><p>When I assumed a new leadership role, I inherited a culture rich with history, strengths, traditions, and stories. The school already possessed a deeply held belief that students could grow regardless of where they started. That mattered. It was more than a slogan. It was part of the school&#8217;s identity. Teachers believed in growth. They believed in possibility. They believed that achievement was not determined solely by starting point.</p><p>That legacy deserved preservation. That legacy deserved protection. That legacy deserved to travel.</p><p>But alongside those strengths existed challenges. Work often happened in silos. Grade levels operated independently. Departments functioned separately. Leadership decisions were sometimes disconnected from teacher voice. People worked hard, but too often they worked alone. And it led to division. Division led to toxicity.</p><p>And while those patterns may have developed for understandable reasons, they were not producing the kind of collaboration needed for future success.</p><p>Those patterns deserved interruption. Not because they were malicious. Because they had become limiting.</p><p>That is where leadership becomes difficult. Because carrying forward the best parts of a culture while burying the unhealthy parts requires discernment. And discernment is rarely applauded in the moment.</p><p>Some people want everything preserved. Others want everything changed. The leader stands in the middle. Listening. Evaluating. Learning. Carrying. Burying.</p><p>That work is difficult because somebody always disagrees. Yet it is necessary because healthy leadership is not about protecting every inheritance. It is about stewarding the right ones.</p><p>And that responsibility brings us to the heart of the lesson.</p><h2><strong>The Heart of the Lesson</strong></h2><p>Every leader inherits two things. The lessons they should carry. And the lessons they should bury.</p><p>Wisdom should travel. Wounds should heal. Service should travel. Ego should heal. Stewardship should travel. Control should heal. Mentorship should travel. Insecurity should heal. Collaboration should travel. Isolation should heal. Compassion should travel. Bitterness should heal.</p><p>Because legacy is not merely measured by what survives us. Sometimes it is measured by what finally ends with us. That may be one of the most sacred responsibilities leadership gives us:</p><p>The opportunity to become a cycle breaker. To interrupt dysfunction. To end unhealthy patterns. To refuse to pass along wounds disguised as traditions. To recognize that not everything inherited deserves preservation.</p><p>Some cycles deserve continuation. Some cycles deserve interruption. Some traditions deserve protection. Some wounds deserve healing.</p><p><strong>Some legacies deserve carrying. Some legacies deserve burying.</strong></p><p>And wisdom is knowing the difference.</p><h2><strong>What This Means for Us</strong></h2><p>For those of us entrusted with leadership, this week asks a difficult question:</p><ul><li><p>What are we passing forward?</p></li></ul><p>Not what are we experiencing. Not what happened to us. Not what frustrated us.</p><ul><li><p>What are we choosing to pass forward?</p></li><li><p>Are we carrying wisdom?</p></li><li><p>Or simply carrying wounds?</p></li><li><p>Are we developing people the way we wish we had been developed?</p></li><li><p>Are we creating cultures where collaboration replaces isolation?</p></li><li><p>Are we preserving what is healthy while improving what is not?</p></li><li><p>Are we willing to honor the leaders who came before us without becoming imprisoned by every decision they made?</p></li></ul><p>Because leadership is not about choosing between preservation and change. Leadership is about discerning which deserves which. And that responsibility may be lonely. But it is also sacred.</p><p>Because every decision we make determines what the next generation inherits from us.</p><h2><strong>Reflection Questions</strong></h2><p>This week let&#8217;s hold a few questions near to our hearts:</p><ol><li><p>What leadership lessons have I inherited that deserve continuation?</p></li><li><p>What leadership patterns have I inherited that should end with me?</p></li><li><p>Have I confused being different with being better?</p></li><li><p>Am I carrying forward wisdom or merely reacting against past wounds?</p></li><li><p>What traditions within my organization deserve protection?</p></li><li><p>What patterns within my organization deserve interruption?</p></li><li><p>How can I become a better steward of both preservation and change?</p></li></ol><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong>A Continued Invitation</strong></h2><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h2><strong>Recognition</strong></h2><p>As this series continues, I find myself increasingly grateful for leaders like &#8220;Doc&#8221; and S.W. Not because they were perfect. No leader is. But because they left behind far more lessons worth carrying than lessons requiring burial.</p><p>They modeled stewardship over status. Service over self. Development over control. Preparation over performance. Children over ego. And as they enter these final weeks before retirement, I find myself appreciating one of the greatest gifts a leader can leave behind:</p><p>A legacy that requires very little correction from those who follow.</p><p>That is a remarkable achievement. It is also a remarkable responsibility.</p><p>Thank you both for the lessons worth carrying. Thank you for the examples worth preserving. Thank you for showing so many of us what healthy leadership can look like when practiced consistently over time.</p><p>And finally, thank you to each of you who continue pulling up a seat to the milk crate each week. Thank you for reading. Thank you for reflecting. Thank you for allowing these stories, lessons, and memories to become part of your own leadership journey.</p><p>As we move toward the final week of this series, I hope these reflections continue honoring the people who shaped us while challenging us to become thoughtful stewards of what we pass forward.</p><p>This week, remember: the future will inherit something from all of us. The question is whether we are passing along wisdom...or simply passing along wounds.</p><p>Identify one lesson worth carrying. Identify one pattern worth burying.</p><p><strong>It matters more than you know.</strong></p>]]></content:encoded></item><item><title><![CDATA[The Cost of Legacy]]></title><description><![CDATA[Lessons from the Leaders Who Never Needed the Spotlight, Part III]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/the-cost-of-legacy</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/the-cost-of-legacy</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 06 Jun 2026 14:01:05 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/5bb3c338-294a-422e-82e7-03a9b3503ada_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>The <a href="https://lessonsfromthemilkcrate.substack.com/p/lessons-from-the-milk-crate">milk crate</a> was never a place where people talked much about success.</p><p>They talked about responsibility. About showing up. About doing what needed to be done whether anyone noticed or not.</p><p>The people who shaped many of us understood something that becomes clearer with age: the things that matter most often require sacrifice.</p><p><a href="https://lessonsfromthemilkcrate.substack.com/p/the-things-we-leave-in-people">Last week</a>, we reflected about legacy not as something we leave behind for ourselves, but as something we leave within others. The confidence we build. The wisdom we pass down. The opportunities we create. The lives we quietly shape through service.</p><p>But that reflection naturally raises another question: If meaningful legacy is what we leave in people, what does it cost to leave something worth leaving?</p><p>Because confidence does not build itself. Children do not develop themselves. Strong families do not happen accidentally. Healthy schools do not appear overnight. Meaningful leadership does not emerge without investment.</p><p>Somebody sacrifices.. Somebody stays late. Somebody arrives early. Somebody carries burdens others never see. Somebody gives more than what is required because they understand that responsibility often extends beyond convenience.</p><p>Yet sacrifice is one of the least celebrated parts of leadership. We celebrate outcomes. We celebrate achievement. We celebrate success. But we rarely celebrate the early mornings, the missed evenings, the difficult decisions, the lonely responsibilities, and the countless unseen moments that made those successes possible. And perhaps that is because everybody wants impact. Few people want the cost attached to it.</p><p>Or as one of my milk crate mentors demonstrated every day through the way he lived:</p><p><strong>Everybody wants the harvest. Few people volunteer for the plowing.</strong></p><p>As I write this week, another one of those milk crate mentors is preparing to close an extraordinary chapter. After forty-six years in educational leadership-S.W. is retiring.</p><p>Forty-six years. Let&#8217;s think about that for a moment-entire generations of students passed through schools during those years. Educational trends came and went. Standards changed (countless times). Technology changed. Buildings changed. Leadership changed. The world changed. And through it all, he kept showing up. Not for a season. Not for a contract. Not for recognition. For forty-six years.</p><p>Because meaningful legacy is rarely built through moments. It is built through consistency.</p><p>And consistency always costs something.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!vpiU!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!vpiU!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!vpiU!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!vpiU!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!vpiU!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!vpiU!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/200888718?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!vpiU!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!vpiU!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!vpiU!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!vpiU!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7d92e989-c185-4d19-9c2e-654016f549b7_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong>Disclaimer: What This Week Is Not</strong></h2><p>This week is not a celebration of performative sacrifice.</p><p>It is not about staying late because we spent the day avoiding the work that needed to be done. Most of us have encountered someone who somehow always appears to be the last one in the building, yet spent much of the day chasing what was enjoyable while postponing what was necessary. They lingered in conversations, gravitated toward the work they preferred, and delayed the responsibilities that required discipline. Then, when everyone else had gone home, they finished what should have already been completed and called it sacrifice.</p><p>That is not sacrifice-that is procrastination wearing a name tag. Real sacrifice begins after responsibility has already been honored.</p><p>This week is also not permission to disengage during the workday because of work completed before sunrise or after sunset. We have all known people who wanted credit for the extra hours while forgetting the responsibility attached to the hours everyone could see.</p><p>The children still need us. The team still needs us. The mission still needs us. Sacrifice does not excuse absence. It deepens responsibility.</p><p>And perhaps most importantly, this week is not about showcasing sacrifice. The people who shaped many of us rarely announced what they were giving up. They simply gave it. They did not post every extra hour. They did not turn every inconvenience into a story. They did not need applause for doing what responsibility required.</p><p>We have all encountered leaders who seemed more interested in making sure everyone knew how hard they worked than in actually serving the people around them. Every sacrifice became a performance. Every extra effort became a headline. Every contribution came attached to a reminder.</p><p>But true sacrifice is usually quiet. The best leaders often carry burdens silently. The best parents rarely keep score. The best mentors often make investments that are never publicly acknowledged.</p><p>And finally, this week is not an invitation to sacrifice the people who matter most. Leadership is a family affair. Whether we realize it or not, our families experience our leadership every day. They experience the long hours. The difficult seasons. The emotional weight. The celebrations. The disappointments. The sacrifices. And while meaningful leadership often requires giving more than what is comfortable, it should never become an excuse to neglect the people who walk beside us. Because one day the title will be gone. The office will belong to someone else. The meetings will continue without us. The opportunities will pass. But family remains.</p><p>Meaningful sacrifice is not about choosing leadership over the people we love. It is about stewarding both well.</p><p>And when I think about responsibility carried with that kind of quiet dignity, my thoughts always return to my father.</p><h2><strong>What Responsibility Looked Like First</strong></h2><p>Growing up, I watched responsibility wear a military uniform.I watched it leave before sunrise. I watched it come home tired. And I watched it go back out again.</p><p>There were seasons when my father would leave for work before daylight. He would spend nearly ten hours at his primary job, come home, eat dinner, change clothes, and head immediately to a second job that often kept him working past midnight. Then he would wake up and do it all again. Not because he enjoyed being tired. Not because someone was applauding him. Not because he wanted recognition. Because his family needed him. Because that was his responsibility.</p><p>What stands out to me now is not simply how hard he worked. It is how little he complained. No speeches. No dramatic reminders. No running tally of sacrifices made. Just consistency.</p><p>Years later, the pattern remained. Five o&#8217;clock mornings. An hour-and-a-half drive to work. A full day on the job. An hour-and-a-half drive home. And somehow, despite all of it, he still found time for family.</p><p>Looking back, I realize he was teaching us something without ever sitting us down for a lesson. Responsibility is not always convenient. Duty is not always comfortable. Love is not always easy. But honorable people carry those responsibilities anyway.</p><p>To this day, I cannot remember hearing him complain about the obligations attached to caring for his family. That is honorable. Because sacrifice attached to purpose becomes service.</p><p>And perhaps that is why the older I get, the more I appreciate the difference between people who talk about commitment and those who quietly demonstrate it.</p><p>Which brings me to another milk crate mentor whose life taught me that lesson every single day.</p><h2><strong>A Milk Crate Lesson Lived</strong></h2><p>Some people teach leadership through presentations. Others teach leadership through presence. S.W. taught it through presence. He was my first administrative partner. The person who helped train me. The leader who gave me a front-row seat to what stewardship actually looks like.</p><p>One lesson he repeated often has stayed with me for years: <em>&#8220;Give 110% every day because any day they can take it from you.&#8221;</em></p><p>At first, it sounded like a work ethic statement. Over time, I realized it was really a stewardship statement. Tomorrow is not guaranteed. The opportunity is not guaranteed. The position is not guaranteed. So while you have the responsibility, honor it fully. And nobody embodied that lesson more consistently than S.W.</p><p>Every morning he arrived long before anyone expected him to. Long before teachers. Long before staff. Long before students. While most of the community was still waking up, he was already walking the building. Checking classrooms. Inspecting facilities. Following up on maintenance concerns. Making sure repairs had been requested. Adjusting plans. Preparing for unexpected changes. Ensuring teachers and students would walk into a building ready for learning.</p><p>Most people never saw those hours. Students certainly didn&#8217;t. Parents rarely knew they existed. Even many staff members benefited from them without realizing how much preparation had already happened before they arrived.</p><p>But S.W. understood something many leaders miss. The experience people have during the day is often built upon preparation they never witness. And preparation was his discipline.</p><p>In those early years together, twenty thousand steps in a day was not unusual. We were constantly moving. Walking classrooms. Checking facilities. Supporting teachers. Meeting with parents. Addressing problems. Solving issues before they became larger issues. Handling the unexpected. And then handling whatever unexpected thing followed that.</p><p>School leadership is not a desk job. At least not when it is done well. And S.W. was always moving. Always preparing. Always anticipating. Always serving.</p><p>What impressed me most, however, was not the activity. It was the consistency. Anyone can work hard occasionally. Few people sustain it year after year. Decade after decade. For forty-six years.</p><p>When the school day ended, he often kept going. Athletic events. Band performances. Community activities. Road games. Saturday competitions. School functions. If students were involved, there was a good chance S.W. would be there. Not because someone required it. Because he believed showing up mattered. And perhaps that is the lesson that stays with me most.</p><p>He understood that leadership is not merely about managing responsibilities. It is about honoring them. There is a difference. One views work as obligation. The other views it as stewardship. And stewardship changes everything. It changes how we arrive. It changes how we prepare. It changes how we serve. It changes how we show up when nobody is watching.</p><p>Looking back now, I realize S.W. was leaving something behind in all of us.</p><p>Not just lessons. Standards. Expectations. Examples. Proof that meaningful leadership requires more than good intentions. It requires commitment. And commitment sustained over forty-six years becomes something remarkable.</p><p>It becomes legacy.</p><p>Which brings us to an important question for leaders today.</p><h2><strong>The Leadership Responsibility We Carry Now</strong></h2><p>The challenge facing leadership today is not a shortage of ambition. It is a shortage of leaders willing to consistently pay the price attached to meaningful influence.</p><p>Many people want impact. Fewer want preparation. Many want authority. Fewer want responsibility. Many want recognition. Fewer want the sacrifices recognition often requires.</p><p>Yet every healthy school, organization, team, and family is built on people willing to do the unseen work. The preparation. The follow-through. The consistency. The difficult conversations. The accountability. The extra effort that never appears on a r&#233;sum&#233;. The reality is that our children deserve leaders who are willing to do more than what is convenient.</p><p>Our teachers deserve leaders who prepare before problems arrive. Our communities deserve leaders who understand that stewardship is not measured by visibility. It is measured by responsibility. And perhaps the greatest challenge facing us today is whether we are willing to embrace the sacrifices attached to the influence we say we want.</p><p>Because meaningful legacy always costs something.</p><h2><strong>The Heart of the Lesson</strong></h2><p>Meaningful legacy is expensive. Not financially. Personally. It costs comfort. It costs convenience. It costs time.It costs energy. It costs discipline. It costs consistency.</p><p>The people who leave the deepest marks on our lives are rarely the people who simply held positions. They are the people who sacrificed something to make our lives better. Parents who worked another shift. Teachers who stayed another hour. Mentors who made another phone call. Veterans who missed another holiday. Leaders who carried another burden. Everybody wants the harvest.</p><p><em>Few people volunteer for the plowing. Yet the harvest never appears without it.</em></p><p>And perhaps that is the lesson S.W. modeled so powerfully over forty-six years. Legacy is not built by what we accomplish once. It is built by what we faithfully do over and over again. Long after motivation fades. Long after excitement disappears. Long after nobody is watching.</p><p>That is where legacy lives.</p><h2><strong>What This Means for Us</strong></h2><p>This week asks us to examine not only what we want from leadership, but what we are willing to give to it:</p><ul><li><p>Are we willing to prepare before others arrive?</p></li><li><p>Are we willing to do work that may never receive recognition?</p></li><li><p>Are we willing to carry responsibilities that nobody else sees?</p></li><li><p>Are we willing to remain faithful when consistency becomes difficult?</p></li></ul><p>Because meaningful legacy is not built through occasional excellence. It is built through daily faithfulness. And daily faithfulness is rarely glamorous. But it changes lives. The question is not whether sacrifice will be required.</p><p>The question is whether what we are sacrificing for is worthy of the cost.</p><h2><strong>Reflection Questions</strong></h2><p>This week I am compelled to hold a few questions near to my heart:</p><ol><li><p>What responsibilities in my life require greater consistency rather than greater recognition?</p></li><li><p>Am I sacrificing for the mission, or am I seeking credit for the sacrifice?</p></li><li><p>What unseen work am I neglecting because nobody else notices it?</p></li><li><p>How do I respond when commitment becomes inconvenient?</p></li><li><p>Have I confused being busy with being responsible?</p></li><li><p>Who modeled quiet sacrifice for me growing up?</p></li><li><p>What kind of legacy is my consistency building today?</p></li></ol><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong>A Continued Invitation</strong></h2><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h2><strong>Recognition</strong></h2><p>This week, I honor my father. Thank you for showing me what responsibility looks like. Thank you for the early mornings, the late nights, the second jobs, the long commutes, and the countless sacrifices that made opportunities possible for our family. Thank you for carrying burdens without complaint. Thank you for teaching us that honorable people fulfill their responsibilities even when doing so is difficult.</p><p>And this week, I especially honor S.W. Forty-six years. Forty-six years of showing up. Forty-six years of preparation. Forty-six years of service. Forty-six years of putting children, schools, educators, and communities first. Thank you for teaching me that leadership begins long before the first meeting and often continues long after everyone else has gone home. Thank you for modeling stewardship instead of status. Preparation instead of performance. Consistency instead of convenience. Thank you for showing a young administrator what it means to honor the responsibility attached to leadership. The schools you served will remember your work. The educators you developed will carry your lessons. The students you impacted will benefit from decisions they may never know you helped make. And generations of leaders will continue walking through doors made possible by your faithfulness.</p><p>That is legacy. Not a title. Not a position. Not a retirement announcement. But forty-six years of quietly making things better for others.</p><p>And finally, thank you to each of you who continue pulling up a seat to the milk crate each week.</p><p>Thank you for reading, reflecting, sharing, and allowing these stories, lessons, and memories to become part of your own leadership journey. </p><p>As we continue this series on legacy, I am grateful that you have chosen to sit on the milk crate with me. I hope these reflections honor the people who shaped us, challenge us to lead with greater intention, and remind us that the most meaningful work we do is often the work nobody else sees.</p><p>This week, do one thing that nobody may ever thank you for. Prepare a little more. Serve a little better. Show up a little earlier. Stay faithful a little longer.</p><p>Because the harvest we hope to leave behind is often growing in work nobody else can see.</p><p><strong>That matters more than you know.</strong></p>]]></content:encoded></item><item><title><![CDATA[The Things We Leave in People]]></title><description><![CDATA[The Legacy You Leave Behind, Part II: Lessons from the Leaders Who Never Needed the Spotlight]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/the-things-we-leave-in-people</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/the-things-we-leave-in-people</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 30 May 2026 14:02:42 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/83595bd7-6854-453e-9de2-009834bf3b68_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>The <a href="https://lessonsfromthemilkcrate.substack.com/p/lessons-from-the-milk-crate">milk crate</a> was never much to look at.</p><p>Just a simple place to sit. A place to listen. A place where stories were passed down before we knew they were becoming lessons. Long before leadership books, professional development sessions, or administrative titles entered the conversation, the milk crate taught us that some of the most important things we inherit are not possessions.</p><p>They are values. They are phrases. They are habits. They are ways of seeing people. They are quiet convictions planted in us by folks who may never know how often we still hear their voices.</p><p>And that is where Week 2 of this legacy series finds us.</p><p><a href="https://lessonsfromthemilkcrate.substack.com/p/the-legacy-you-leave-behind">Last week</a>, we reflected on the truth that legacy is not something we chase. This week, we go a step deeper: <em>Legacy is what we leave in people</em>. Not what we collect. Not what we display. Not what we build around our own name. But what remains inside others because we loved, served, corrected, encouraged, protected, and poured into them well.</p><p>Because the milk crate was never just about who sat there.</p><p>It was about who got up from it carrying something they did not have before.</p><p>And that leads us to an important reminder about what this week is not.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!wwao!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!wwao!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!wwao!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!wwao!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!wwao!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!wwao!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg" width="1024" height="1024" 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srcset="https://substackcdn.com/image/fetch/$s_!wwao!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!wwao!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!wwao!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!wwao!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6ce5f14f-5d84-4b7b-90cc-7c99eb5529b9_1024x1024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong>Disclaimer: What This Week Is Not</strong></h2><p>This week is not about being remembered.</p><p>It is not about buildings named in our honor, hallways dedicated in our memory, conference rooms carrying our names, plaques placed on walls, or ceremonies where people speak kindly once we are no longer in the room.</p><p>Very few of us will ever have a school named after us. Most of us will not have a wing, a scholarship, a street sign, or even a framed photograph hanging permanently in a main office somewhere.</p><p>And that is okay. Because if our understanding of legacy depends on institutional remembrance, then we have already made legacy too small.</p><p>This week is also not about accumulation.</p><p>It is not about collecting successful people around us like trophies. It is not about claiming mentees after they have already become successful. It is not about attaching our names to people we did not develop, sacrifices we did not make, or growth we did not nurture.</p><p>We have all encountered people who want to be associated with success more than they want to invest in people. They want to point to talented individuals and say, &#8220;They were on my team,&#8221; or &#8220;I mentored them,&#8221; or &#8220;I helped shape them,&#8221; when the truth is they may have done very little to cultivate that growth.</p><p>Sometimes they did not water the seed. They simply showed up when the flower bloomed.</p><p>And sometimes, if we are honest, the only leadership lesson some people leave behind is a clear understanding of what not to do.</p><p>What not to become. How not to treat people. How not to lead children. How not to confuse authority with wisdom. How not to mistake control for development.</p><p>Even those lessons matter, though they come with a cost. They remind us that legacy is not neutral. We are always leaving something in people-confidence or insecurity, courage or caution, healing or wounds, clarity or confusion.</p><p>This week is not about remembrance for our own sake. It is about responsibility for the sake of others.</p><p>Because legacy is not left <em>for us</em>. Legacy is what we leave <em>in them</em>.</p><p>In the child who begins to believe they are capable. In the teacher who finds courage to lead. In the staff member who goes back to finish the degree because someone saw more in them than they saw in themselves. In the young leader who walks into a difficult room years later and still hears a mentor&#8217;s voice saying, &#8220;Stay steady. Do the right thing. Keep children first.&#8221;</p><p>That is legacy. Not recognition. Not reputation. <strong>Transformation</strong>.</p><p>And when I think about what it means to leave something meaningful in people, my mind first travels back to a woman who taught me sacrifice long before I had language for leadership.</p><h2><strong>What My Grandmother Left in Us</strong></h2><p>When I think about legacy living inside people, my mind goes back to my grandmother. Not because she accumulated wealth or recognition.</p><p>Quite the opposite.</p><p>By most worldly standards, she lived a very modest life. Hard work. Meager possessions. Quiet sacrifice. Yet somehow, even now, years later, her influence still lives inside the people she touched.</p><p>Because what she left behind was never really about things. It was about what people carried away from her presence.</p><p>She had a way of making people feel like they belonged. Her table was always full. Extended family. Strangers from church. Folks new to town. Children who were not hers by blood but became hers through love, consistency, and care. Nobody arrived wondering whether there was enough room for them. She simply made room.</p><p>And looking back now, I realize she was leaving something in people every time she did that.</p><p>She was teaching us generosity without announcing the lesson. She was teaching us hospitality without calling it ministry. She was teaching us that people mattered more than possessions long before many of us had language for servant leadership.</p><p>Birthdays and Christmases were often made from whatever she could stretch together. I am fairly certain there were Green Bax Stamps quietly exchanged at the Piggly Wiggly more than once just to make sure someone else felt loved. Prescription medications were sometimes beyond her budget. Yet somehow she still found ways to give.</p><p>Not because giving was easy. Because loving people mattered to her more than comfort did.</p><p>And perhaps the most powerful thing she left behind was not what she provided materially. It was what she modeled consistently.</p><p>Faith. Sacrifice. Steadiness. Compassion. The quiet understanding that people are not interruptions to our lives-they are the reason for it.</p><p>Even now, years later, pieces of her still surface in our family. In how we feed guests. In how we treat strangers. In how we show up for one another during difficult seasons. In the instinct to make room at the table even when resources feel limited.</p><p>That is legacy.</p><p>Not simply what someone leaves <em>to</em> us. <strong>But what they leave </strong><em><strong>in</strong></em><strong> us</strong>.</p><p>My grandmother did not leave behind a monument. She left behind a way of loving people that continues reproducing itself through generations.</p><p>And perhaps that is why the best leaders often remind us less of celebrities and more of caretakers-people whose greatest impact was not what they accumulated, but what they cultivated in others over time.</p><p>Which brings me back to one of my milk crate mentors, &#8220;Doc,&#8221; whose leadership carried that very same spirit of pouring into people for the sake of what might continue long after she was gone.</p><h2><strong>The Legacy Doc Lived</strong></h2><p>This week is still, in many ways, a recognition of &#8220;Doc.&#8221; Not only because she is retiring this month. But because her life and leadership help explain what this week&#8217;s message is really about.</p><p>Doc taught legacy without needing to announce that she was teaching it.</p><p>She lived it.</p><p>For years, I watched her put others first. Children first. Families first. Then the people she led. And she did it with a steadiness that made service feel less like an initiative and more like a conviction.</p><p>There was nothing performative about it. Nothing ornamental. Nothing designed for applause. She simply believed that if you were blessed to lead, then you were responsible for developing the people entrusted to your care.</p><p>Not using them. Not controlling them. Not keeping them small so you could remain comfortable. Developing them.</p><p>And that distinction matters.</p><p>Because some leaders are threatened when the people around them grow. They become uneasy when others develop strengths beyond their own. They guard information. They limit access. They quietly close doors because they are afraid someone else&#8217;s gift will expose their insecurity.</p><p>But Doc did not lead that way. </p><p>She poured into people without fear. She invested without hesitation. She developed others without needing to remain the most impressive person in the room. And more often than not, her investment was not simply about immediate impact on the school she was leading. It was bigger than that. She carried a deep sense of responsibility to the future of education itself.</p><p>She would remind us often that we would soon replace her.</p><p>&#8220;How many years do you have until retirement?&#8221; she would ask.</p><p>And some of us would answer with numbers that sounded almost impossible at the time.</p><p>&#8220;Fifteen.&#8221; &#8220;Twenty.&#8221; &#8220;Twenty-five.&#8221;</p><p>And she would laugh and say something like, &#8220;Twenty years? There&#8217;s no telling what education will look like in another twenty years. The children may be running the school and the parents might be running y&#8217;all. But I know one thing-we are going to make sure you all are ready to lead, because I&#8217;ll be at the house.&#8221;</p><p>Now, she said it jokingly. But there was so much truth tucked inside that humor.</p><p>That was Doc.</p><p>She could make you laugh and leave you carrying a leadership charge at the same time. Because beneath the joke was a sacred seriousness: she understood that leadership is temporary, but responsibility is generational.</p><p>She knew she would not always be in the chair. She knew the work would continue after her. She knew children yet unborn would one day walk into schools shaped by the people she was developing now.</p><p>That is legacy vision.</p><p>Not merely asking, &#8220;How well are we doing today?&#8221; But also asking, &#8220;Who is being prepared to lead tomorrow?&#8221;</p><p>I can recall countless times when she encouraged office staff or paraprofessionals to go back and finish their degrees because she saw something in them that they may not have fully seen in themselves. She could look at someone doing one job and already imagine the teacher, leader, advocate, or mentor they might become.</p><p>She pushed teachers to explore leadership experiences. She encouraged professional development opportunities. She opened doors when people were ready. And sometimes, just as importantly, she helped remove barriers that stood in the way.</p><p>She did not merely say, &#8220;You should grow.&#8221; She helped people find the path.</p><p>That is a different kind of leadership. Anybody can tell people to improve. Not everybody will help carry the obstacles out of the hallway.</p><p>Doc made it a regular practice to mentor teachers working on leadership degrees. She brought them into administrative meetings. She showed them how decisions were made. She taught them how to think through master schedules, organize events, plan systems, manage responsibilities, and understand the moving pieces of school leadership that many people never see from the outside.</p><p>She did not hoard knowledge. She handed it down.</p><p>And she did it not for self-promotion, not for recognition, not so people would one day stand and say, &#8220;Look what Doc did.&#8221;</p><p>She did it as an act of service to the field of education. She did it because children needed future leaders ready for the work. She did it because she understood that a leader&#8217;s influence should not end at their office door.</p><p>That is legacy. Leaving fingerprints on lives and careers that will transcend generations.</p><p>A child taught by someone she developed. A school strengthened by someone she encouraged. A future principal prepared because she made room at the table. A young educator still standing because she was steady enough to help them survive the early years. A leader making wiser decisions years later because somewhere in the back of their mind, they still hear Doc asking the right question at the right time.</p><p>That is not just mentorship. That is multiplication.</p><p>And as we look at leadership today, I believe that kind of multiplication is not simply admirable.</p><p>It is urgently needed.</p><h2><strong>The Leadership Responsibility We Carry Now</strong></h2><p>We are leading in a time that desperately needs people who are willing to leave something meaningful in others.</p><p>Education is changing quickly. Communities are changing. Families are carrying more. Children are bringing more into classrooms than many of us can fully comprehend. Teachers are navigating pressures that extend far beyond lesson plans. Leaders are being asked to manage systems, emotions, crises, policies, expectations, and human needs all at once.</p><p>And in moments like this, leadership cannot simply be about maintaining operations. It has to be about developing people. Because the work is too heavy for isolated leadership. The future is too uncertain for selfish leadership. The needs are too urgent for leaders who only want to be remembered.</p><p>Those of us blessed to lead in this season have a responsibility to ask better questions.</p><ul><li><p>Who are we preparing?</p></li><li><p>Who are we encouraging?</p></li><li><p>Who are we correcting with dignity?</p></li><li><p>Who are we giving access to rooms where learning happens?</p></li><li><p>Who are we helping see gifts in themselves that they have not yet named?</p></li><li><p>Who are we making stronger, wiser, steadier, and more courageous?</p></li></ul><p>Because there is a difference between supervising people and developing them.</p><p>Supervision watches performance. Development invests in potential. Supervision can manage today. Development prepares tomorrow. And if we are honest, our schools and organizations need more than managers of the moment. They need leaders with enough humility to recognize that the goal is not to be irreplaceable.</p><p>The goal is to prepare others so well that the mission remains strong long after we move on. That is not weakness. That is stewardship.</p><p>A leader who refuses to develop others may protect their position temporarily, but they weaken the future permanently.</p><p>A leader who pours into others may not always receive immediate credit, but they leave strength behind in places their name may never be mentioned.</p><p>That is the kind of leadership we need now. Leaders who are not afraid of gifted people. Leaders who do not shrink the room to protect their ego. Leaders who create access. Leaders who share wisdom. Leaders who make people better and then celebrate when they rise.</p><p>Because when leaders develop others well, they do more than improve a department, school, or organization. They influence people they may never meet.</p><p>A child ten years from now may benefit from a teacher developed today. A school twenty years from now may be led by someone encouraged today. A family tomorrow may be served better because someone was mentored, challenged, and prepared today.</p><p>That is the sacred math of legacy. What we pour into one person can multiply into the lives of many.</p><p>And that brings us to the heart of the lesson.</p><h2><strong>The Heart of the Lesson</strong></h2><p>Legacy is not what we leave behind with our name on it. Legacy is what we leave inside people.</p><p>The courage we give them. The confidence we help restore. The wisdom we pass down. The standards we model. The access we create. The prayers we whisper. The correction we offer with love. The belief we lend until they can believe for themselves.</p><p>True legacy is not built by collecting successful people around us. It is built by developing people before success is visible. It is built when we see the future teacher in the paraprofessional. The future leader in the quiet educator. The future advocate in the student who just needs one adult to notice. The future difference-maker in someone still unsure of their own capacity.</p><p>That is why legacy is not ownership. It is investment. It is not claiming people. It is cultivating them. It is not saying, &#8220;Look who I produced.&#8221; It is saying, &#8220;Thank God I had the chance to pour into someone who will go farther than I ever could.&#8221; And maybe that is the real mark of mature leadership.</p><p>We stop needing to be the final destination. We become part of someone else&#8217;s beginning. That is what my grandmother did at her table. That is what Doc did in her leadership. That is what the best educators do every day. They leave something in people that keeps feeding them long after the meal is over.</p><p>And if we take that seriously, then this week&#8217;s lesson cannot remain sentimental.</p><p>It has to become practical.</p><h2><strong>What This Means for Us</strong></h2><p>For those of us entrusted with leadership, this week asks us to examine what people are carrying away from us.</p><p>Not what they say about us publicly. Not whether they remember our title. Not whether they attach our name to their success. But what we leave in them.</p><ul><li><p>Do people leave our presence feeling smaller or stronger?</p></li><li><p>Do they leave with fear or clarity?</p></li><li><p>Do they leave more dependent on us or more prepared for what comes next?</p></li><li><p>Do they feel guarded around us or developed by us?</p></li><li><p>Do they become more courageous because we believed in them?</p></li><li><p>Do they understand the mission more deeply because we modeled it consistently?</p></li></ul><p>This matters because leadership is never confined to the present moment. Every interaction deposits something. Every decision teaches something. Every meeting, correction, encouragement, silence, opportunity, and response leaves residue.</p><p>We are always placing something in people. The question is whether it is worth carrying.</p><p>And for those of us in education, that responsibility becomes even more sacred because children are watching more than they are listening. Young educators are learning more than we realize. Staff members are interpreting what we truly value by what we consistently practice.</p><p>We cannot merely talk about development. We must make room for it. We must invite people to the table. We must explain the why behind decisions. We must correct without humiliation. We must celebrate without jealousy. We must prepare people for rooms we may never enter with them. We must be willing to say, &#8220;You are ready,&#8221; and then open the door. And one day, when we are no longer in the daily work, the hope is not that everyone remembers our name. </p><p>The hope is that someone leads better because we poured into them. Someone serves longer because we encouraged them. Someone treats children with more care because they watched us do it first. Someone believes they can because we believed they could before they had evidence.</p><p>That is legacy. Not remembrance. Residue. Not recognition. Responsibility. Not monuments. Multiplication.</p><p>And perhaps that is the question we carry with us this week from the milk crate into the work.</p><p>What are we leaving in people?</p><h2><strong>Reflection Questions</strong></h2><p>This week I feel compelled to hold a few questions near to my heart:</p><ol><li><p>What are people carrying away from my leadership-confidence, clarity, courage, fear, frustration, or uncertainty?</p></li><li><p>Am I developing people for their future, or simply using their gifts for my present needs?</p></li><li><p>Who around me may need encouragement, access, or opportunity to grow into what I already see in them?</p></li><li><p>Have I ever wanted to be associated with someone&#8217;s success without honestly investing in their development?</p></li><li><p>What lessons did I learn from leaders who showed me what not to do, and how am I making sure those patterns do not continue through me?</p></li><li><p>Do I celebrate when those I lead grow beyond me, or do I secretly feel threatened by their strength?</p></li><li><p>What is one practical way this week I can pour wisdom, access, encouragement, or belief into someone else?</p></li></ol><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong>A Continued Invitation</strong></h2><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h2><strong>Recognition</strong></h2><p>This week, I honor my grandmother, whose life taught me that legacy is not measured by what we keep, but by what we give away. She left no monument that I know of, no building bearing her name, no institutional recognition that could ever fully capture her worth. But she left a table. She left faith. She left generosity. She left family in people who were not related by blood. She left a way of loving that still teaches me.</p><p>And this week, I especially honor Doc. Doc, thank you for living the lesson before many of us fully understood it. Thank you for putting children first without hesitation. Thank you for seeing promise in people before they saw it in themselves. Thank you for encouraging staff members to finish degrees, teachers to pursue leadership, and future administrators to step closer to the work rather than simply admire it from a distance. Thank you for opening rooms, explaining systems, sharing knowledge, removing barriers, and reminding us that the work was never supposed to end with us. Thank you for developing people without fear that their strengths might one day exceed your own. Thank you for showing us that true leaders do not hoard wisdom. They hand it down. They multiply it. They trust it in the hands of the next generation. Your legacy will not only live in memories of your leadership. It will live in classrooms, offices, hallways, decisions, children, families, and leaders shaped by the people you poured into. Some of those lives will never know your name. But they will still be touched by what you left in us. And that may be one of the most beautiful legacies of all.</p><p>This week, pour into someone who may never be able to repay you. Encourage the person still becoming. Open a door. Share what you know. Leave something good in the people entrusted to your care.</p><p><strong>It matters more than you know.</strong></p>]]></content:encoded></item><item><title><![CDATA[The Legacy You Leave Behind]]></title><description><![CDATA[Part I: The Leaders Who Never Needed the Spotlight]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/the-legacy-you-leave-behind</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/the-legacy-you-leave-behind</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 23 May 2026 13:02:09 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/8af16b19-ee2f-44d8-892d-b9fe742ba034_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>The <a href="https://lessonsfromthemilkcrate.substack.com/p/lessons-from-the-milk-crate">milk crate</a> was never just a place to sit.</p><p>It was a classroom before we understood what leadership development was. A front porch before strategic plans and organizational charts. A gathering place where wisdom traveled through stories instead of PowerPoints. Long before many of us ever occupied offices, carried titles, or supervised anyone, there were people sitting on figurative milk crates teaching us what mattered most-not through speeches, but through how they lived.</p><p>And what I&#8217;ve come to realize as this school year closes is this: the people who shaped us most were rarely the people chasing influence.</p><p>They were the people carrying responsibility with humility.</p><p>This year feels bittersweet because two more of my milk crate mentors have retired this year. Two more individuals whose fingerprints rest quietly on generations of children, educators, leaders, and communities have stepped away from the daily work. And as I reflected on their transition this week, I found myself thinking deeply about one of them-my first mentor - &#8220;Doc&#8221;- and what she taught us about legacy.</p><p>Not the kind people manufacture. The kind people leave behind when they are too busy serving others to think about themselves. Because true legacy is rarely built by people obsessed with having one. And perhaps that is where this week&#8217;s reflection begins.</p><p><em>But before we talk about what legacy truly is, we probably need to address what legacy is not.</em></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!56Tn!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!56Tn!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!56Tn!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!56Tn!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!56Tn!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!56Tn!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg" width="1024" height="1024" 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srcset="https://substackcdn.com/image/fetch/$s_!56Tn!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!56Tn!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!56Tn!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!56Tn!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4b25c2b5-e935-4a20-9ac5-280b5cbcf51b_1024x1024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>Disclaimer: What This Week Is Not</strong></h3><p>This week is not about titles.</p><p>It is not about recognition. It is not about popularity, applause, plaques, social media visibility, branded clothing, organizational perks, or carefully curated leadership personas. Because if we are honest, many of the loudest pursuits of &#8220;legacy&#8221; are actually pursuits of ego dressed in professional language.</p><p>Too often, leadership culture confuses visibility with value. We sometimes celebrate charisma more quickly than character, position more quickly than preparation, and recognition more quickly than responsibility. And somewhere along the way, people begin believing legacy can be manufactured through politics, maneuvering, or self-promotion rather than earned through service, sacrifice, consistency, and stewardship.</p><p>There are environments where individuals aspire to lead yet invest very little in learning deeply about the work itself. Little curiosity about mastering their craft. Little hunger for growth. Little willingness to study, observe, sacrifice, or develop quietly before pursuing greater responsibility. Yet ambition alone can sometimes create the illusion of readiness.</p><p>And ambition itself is not the problem. Ambition can be healthy. The danger comes when aspiration outruns preparation.</p><p>Because leadership was never meant to be a race toward position. Leadership is stewardship. And stewardship requires humility, correction, patience, emotional maturity, and a willingness to keep learning long after titles arrive. Eventually the weight of responsibility exposes what recognition tried to conceal.</p><p>There are also seasons where organizations encounter leaders who contribute very little toward growth, vision, development, or stability, yet become deeply skilled in criticism. Every idea is flawed. Every system is broken. Everyone else becomes the problem. (Almost as if criticizing everyone else adds value to the leader&#8217;s place in the organization.)</p><p>And over time, it becomes evident that some leadership styles are not truly designed to strengthen people-but to diminish them. There are leaders who unintentionally minimize the value of others as a way of protecting fragile views of themselves.</p><p>But healthy leadership develops people. Insecure leadership diminishes them. One builds confidence. The other manufactures dependency.</p><p>And if we sit on the milk crate long enough, eventually we learn the difference between leaders who cultivate growth and leaders who quietly drain it from the room.</p><p>There are also moments where leadership becomes overly consumed with what can be gained from service rather than what can be given through it. More recognition. More visibility. More privileges. More affirmation. More personal benefit attached to professional responsibility.</p><p>And that posture becomes dangerous when the mission slowly shifts away from children, people, or purpose-and toward self. Because self-serving leadership rarely reveals itself all at once.</p><p>Usually it appears in smaller ways first.</p><p>The inability to celebrate others. The constant need for credit. The discomfort when someone else shines. The obsession with visibility.<br>The attachment of personal worth to public recognition.</p><p>And perhaps that is why leaders like &#8220;Doc&#8221; stand out so clearly in my memory now. Because she never spent energy trying to convince people she mattered.</p><p>You simply felt her impact everywhere.</p><p>In the confidence students carried. In the stability younger educators found around her. In the way people straightened up when she walked into a room-not out of fear, but respect. In the quiet trust she built over decades of consistency, compassion, wisdom, and integrity.</p><p>She was never chasing visibility. And ironically, that is exactly what made her unforgettable. There are people whose names become known because they demanded attention.</p><p>Then there are people whose names become revered because they changed lives.</p><p>Doc belonged to the second group.</p><p><em>And maybe that distinction is what carried my reflection toward the people who modeled legacy best in my own life.</em></p><h3><strong>Quiet Pride and Humble Service</strong></h3><p>As I reflected this week, my thoughts drifted toward my father.</p><p>A Navy and Army veteran. Quietly proud. The kind of proud that did not require an audience.</p><p>My father served more than two decades in uniform. Active duty assignments. Nuclear submarines in the 1980s. Deployments around the world. Missions, operations, and only a few stories he still only shares in pieces decades later. (And usually only when my mother is not within immediate hearing distance.)</p><p>He earned commendations we never knew about at the time. Served in places most people will never see. Sacrificed years of comfort, routine, and normalcy in service to something greater than himself. Yet if someone thanked him for his service or tried to celebrate him publicly, he almost always responded the same way:</p><p>&#8220;I&#8217;m just doing my job.&#8221;</p><p>Simple words. But profound posture. There was never arrogance attached to his service. Never performance. Never a hunger for validation. Yet there was still a quiet dignity about how he carried his responsibility.</p><p>His office shelves still hold reminders of those years-model ships, photographs, small pieces of memorabilia gathered across decades of service. Every now and then he reflects on stories from deployments long past, and in those moments you can hear both humility and honor existing side by side.</p><p>What shaped me most was not merely what he accomplished. It was what he valued. As part of a multigenerational military family whose lineage stretches across nearly every major American conflict over the last 250 years, he instilled in us a simple but grounded patriotism. Not performative. Not loud. Not attention-seeking. Just faithful.</p><p>And now, looking back, I realize the greatest thing he passed down was not stories. It was posture. The understanding that dignity does not require spectacle.</p><p>That lesson would eventually follow me far beyond home and into the work of leadership itself.</p><h3><strong>The Mentors Who Led From Behind</strong></h3><p>One of my mentors-&#8220;Doc&#8221;-once told me: &#8220;Be careful who you allow to mentor you. Some people want to <em>be called</em> mentors more than they actually want to mentor others. And some simply have no idea how to do the job but think they do.&#8221;</p><p>At the time, I understood the words academically. Years later, I understand them spiritually.</p><p>Because Doc was never interested in collecting followers, building personal platforms, or attaching herself to successful people for visibility. She genuinely believed leadership was an act of stewardship. She believed developing people mattered more than controlling them. And perhaps most importantly, she understood that real leadership requires enough security within yourself to help others shine without feeling threatened by their growth. That is increasingly rare.</p><p>What always stood out about her was not simply what she accomplished professionally-though she accomplished a great deal. It was <em>how</em> she carried people.</p><p>Young educators felt protected around her. Students felt seen. Veteran staff members felt respected. She had the rare ability to correct people without crushing them. Even difficult conversations somehow carried dignity attached to them. And she carried herself with the kind of authority that never needed performance attached to it.</p><p>No unnecessary speeches. No constant reminders about titles. No obsession with recognition. Just steady leadership. Consistent leadership. The kind of leadership that quietly becomes part of the foundation holding an organization together.</p><p>And one thing she reminded many of us constantly was this: &#8220;This is not our time in the spotlight. We&#8217;ve had our turn. This is the children&#8217;s time.&#8221;</p><p>She did not just say that. She lived it.</p><p>She celebrated students loudly while remaining personally humble. She pushed younger educators forward instead of guarding territory. She believed children deserved the front of the stage while adults learned to find joy in standing behind the curtain helping them succeed.</p><p>That lesson feels especially sacred to me now. Because in a world where so many leaders are fighting to remain center stage, Doc taught many of us the beauty of stepping aside so somebody else could grow.</p><p>And perhaps that is why her retirement feels emotional for so many people. Not because a position changed. But because people like that leave fingerprints on lives.</p><p>You cannot measure their impact by organizational charts or plaques on walls. Their legacy lives in the people they steadied, the children they encouraged, the educators they protected, and the leaders they quietly shaped long before those individuals even realized they were being shaped.</p><p>Looking back now, I realize something profound: &#8220;Doc&#8221; never chased legacy.</p><p>She simply lived in service long enough for legacy to grow naturally around her.</p><p><em>And if we are honest, that lesson feels especially urgent in today&#8217;s professional climate.</em></p><h3><strong>A Culture That Confuses Visibility With Value</strong></h3><p>We are living in a professional culture increasingly obsessed with visibility.</p><p>Everyone wants the microphone. Everyone wants the title. Everyone wants influence, authority, branding, recognition, and rapid advancement. Yet fewer people seem interested in the hidden disciplines that sustain meaningful leadership over time.</p><p>Patience feels outdated. Apprenticeship feels inconvenient. Humility feels undervalued.</p><p>There are individuals pursuing leadership who have never truly learned how to serve. People demanding authority without demonstrating accountability. Professionals seeking elevation while resisting correction, reflection, or growth.</p><p>And sadly, organizations sometimes reward charisma faster than character. (I can recall several times sitting on interview panels where credit was given to candidates who spoke eloquently but said very little, while those who were highly capable paled in comparison.)  But charisma cannot sustain children. Performance cannot nurture communities. And titles cannot replace integrity.</p><p>The leaders leaving the deepest impact right now are often not the loudest ones in the room. They are the consistent ones. The steady ones. The people quietly mentoring younger staff members after hours. The custodians who know every child&#8217;s name. The cafeteria workers offering encouragement. The teachers staying late to help struggling students. The assistant principals de-escalating difficult situations with compassion. The veteran educators protecting young teachers from burnout.</p><p>Most of them will never trend online. Most will never receive major recognition. Yet every healthy organization is standing on the shoulders of people like that.</p><p>Quiet leaders. Steady leaders. Faithful leaders. The kind of leaders many of us were fortunate enough to encounter through people like Doc.</p><p>Leaders who taught us that influence is not measured by how often your name is mentioned in meetings, but by how many people walk stronger because you poured into them.</p><p>And maybe that is why so many transformational leaders become emotional landmarks in our lives. Long after policies change and buildings empty, we still hear their lessons echoing in our decisions, our leadership, and even the way we carry ourselves professionally.</p><p>And perhaps history will remember them far longer than the individuals who spent all their energy trying to be noticed.</p><p><em>Because eventually we all discover the same truth: legacy is not determined by how loudly people saw us, but by how deeply people were changed because we were there.</em></p><h3><strong>The Heart of the Lesson</strong></h3><p>Legacy is not something you chase. It is something you leave behind while serving faithfully.</p><p>The people who impacted many of us most were rarely obsessed with becoming unforgettable. They were simply committed to doing the right thing consistently, humbly, and well.</p><p>That is why the greatest leaders often do not look like celebrities. They look like servants. They look like mentors staying late. Parents sacrificing quietly. Veterans carrying duty with humility. Educators protecting children. Leaders correcting with compassion. People choosing integrity when shortcuts would be easier. And perhaps the deepest legacies are built in moments nobody applauds.</p><p>Because true leadership does not constantly ask: &#8220;Are people noticing me?&#8221;</p><p>True leadership asks: &#8220;Are people becoming better because I was here?&#8221;</p><p>That is the difference. One seeks attention. The other leaves transformation.</p><p>And only one of those survives long after the spotlight fades.</p><h3><strong>What This Means for Us</strong></h3><p>For many of us, this reflection demands an honest examination of motive.</p><ul><li><p>Why do we want influence?</p></li><li><p>Why do we pursue leadership?</p></li><li><p>Why do we desire recognition?</p></li></ul><p>Because eventually leadership exposes the difference between those who want to serve and those who simply want to be seen serving.</p><p>This week reminds us that legacy is built slowly.</p><p>In ordinary moments. In unseen sacrifices. In consistent character. In how we treat people who cannot advance our careers. In whether children become stronger, safer, wiser, and more hopeful because we entered their lives.</p><p>And perhaps the question we should all wrestle with is not whether people will remember our names.</p><p>But whether people were genuinely better because we carried the responsibility we were given with humility and care.</p><h3><strong>Reflection Questions</strong></h3><p>This will as I reflect on legacy, I will be holding a few questions near to my heart:</p><ol><li><p>Are we more focused on being recognized, or being useful?</p></li><li><p>Have we confused visibility with value?</p></li><li><p>In what ways are we investing in growth rather than simply pursuing position?</p></li><li><p>Do the people we lead feel developed or diminished under our leadership?</p></li><li><p>Are we building a legacy rooted in service-or a reputation rooted in self?</p></li><li><p>Who modeled quiet, faithful leadership for us long before we understood its value?</p></li><li><p>What unseen habits are shaping the legacy we will eventually leave behind?</p></li></ol><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong>A Continued Invitation</strong></h2><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h3><strong>Recognitions</strong></h3><p>This week I honor the mentors who taught many of us how to lead without demanding applause. The ones who quietly stayed late, guided students, protected staff, corrected us with grace, and reminded us that leadership was never about ego.</p><p>I honor the educators and support staff who continue showing up daily not for recognition, but because children deserve consistency, compassion, and care.</p><p>I honor my father, whose service taught me that humility and honor can coexist beautifully.</p><p>I especially honor &#8220;Doc,&#8221; whose leadership shaped far more people than she will probably ever fully know. Thank you for modeling strength without arrogance. Correction without humiliation. Leadership without performance.<br>Service without self-promotion.</p><p>Thank you for reminding many of us that children belong in the spotlight while adults learn the sacred work of standing faithfully behind the curtain.</p><p>Thank you for showing us that legacy is not built through chasing attention, but through quietly carrying responsibility with integrity year after year after year.</p><p>And thank you for proving that some of the most transformational leaders rarely ask for recognition at all.</p><p>Yet somehow leave pieces of themselves in every life they touch. </p><p>And I honor those other milk crate leaders who never chased legacy at all. Yet somehow left it everywhere they went.</p><p>This week, choose service over spotlight, growth over applause, and stewardship over status.</p><p>Because the legacy we leave behind is often being built in the moments nobody notices.</p><p><strong>And that matters more than we know.</strong></p>]]></content:encoded></item><item><title><![CDATA[Love Enough to Correct]]></title><description><![CDATA[Why Leaders Must Address What Harms the Mission]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/love-enough-to-correct</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/love-enough-to-correct</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 16 May 2026 14:03:00 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/f79499f6-01a0-43ce-9e1d-885703ddb63f_1536x1024.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>There are some lessons you don&#8217;t learn in a leadership conference. You learn them sitting still.</p><p>Long before the titles, the meetings, the strategic plans, and the difficult conversations, there was a <a href="https://lessonsfromthemilkcrate.substack.com/?utm_campaign=profile_chips">milk crate</a>. Turned upside down in a bus lot. Resting beside a few garbage cans and an old water hose, with stains that had stories attached to them. A place where listening happened before speaking. A place where observation became wisdom.</p><p>The milk crate reminds me that leadership was never first about authority. It was about discernment. Knowing when to speak. Knowing when to stay silent. Knowing when to laugh something off. And knowing when the moment demanded that somebody draw a line.</p><p>Because healthy leadership is not passive. And silence is not always peace.</p><p>Sometimes love requires interruption.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!y1ry!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!y1ry!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!y1ry!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!y1ry!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!y1ry!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!y1ry!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/197994677?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!y1ry!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!y1ry!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!y1ry!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!y1ry!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F212e0412-0031-4986-bcd6-da377613356b_1024x1024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong>Disclaimer: What This Week Is </strong><em><strong>Not</strong></em></h2><p>Before we go further, let&#8217;s be clear about something.</p><p>This reflection is not about becoming combative leaders. It is not permission to become cynical, reactive, hypercritical, or exhausting to the people we lead.</p><p>Every frustration does not deserve a microphone. Every disagreement does not require confrontation. And every negative comment does not deserve our emotional energy. (Read more <a href="https://lessonsfromthemilkcrate.substack.com/p/listen-to-the-wind-not-just-the-weather">here</a> about "Listening to the Wind&#8221;)</p><p>Discernment matters.</p><p>Part of mature leadership is learning the difference between what is irritating and what is dangerous. Some things are simply personality differences. Some things are rooted in misunderstanding. Some things are temporary growing pains. And some things-if left unchecked-become poison to culture, morale, and ultimately to children.</p><p>We cannot respond to everything. But we must address what matters. And when we do address difficult things, we must do so consistently and in love.</p><p>Not retaliation. Not humiliation. Not emotional venting disguised as &#8220;honesty.&#8221;</p><p>We lead people. We are not called to wound them.</p><p>Too many leaders confuse correction with punishment. But the best leaders understand that accountability is stewardship. We correct because we care. We confront because we are protecting something sacred. And if we are honest, sometimes people simply do not know better yet. (Yet, we also have to recognize that some people are not ready to receive accountability, and will simply remix it and publish it as victimhood - but that is another blog for another week&#8230;)</p><p>Every shortcoming is not intentional. Every inconsistency is not rooted in malice. Every misstep is not rebellion.</p><p>Sometimes people are tired. Sometimes they are immature. Sometimes they are carrying burdens we cannot see. Sometimes they are simply untrained. So we must resist the temptation to assign evil motives to human imperfection.</p><p>Still&#8230; there are moments when leadership requires us to lovingly say: &#8220;This cannot continue.&#8221;</p><p>And amen, somebody, <em>that</em> is the uncomfortable work of leadership.</p><h2><strong>Drawing the Line</strong></h2><p>My father has always been a man of few words. The older I get, the more I realize how much power there is in that kind of restraint. He never felt the need to dominate a room with noise. He did not argue for sport. He did not engage in endless back-and-forth debates trying to prove himself right. In fact, one of the things he often taught us growing up was simple:</p><p>&#8220;You don&#8217;t try to reason with crazy people.&#8221;</p><p>And another favorite:</p><p>&#8220;You don&#8217;t respond to the ramblings of fools.&#8221;</p><p>Now, as a child, I thought those statements were mostly about avoiding drama (and honestly, they probably were). But over time, I realized there was deeper wisdom underneath them. Dad understood that not every battle deserves your energy. Not every comment deserves your response.</p><p>But he also taught us something equally important: There comes a moment where you draw the line.</p><p>And when my father drew the line, everybody knew it. What fascinated me was how rarely it involved yelling. Rarely involved insults. Rarely involved theatrics. He had a way of resetting structure and boundaries with calm, undeniable truth. Simple statements. Clear expectations. Facts nobody could really argue with.</p><p>No character assassination. No emotional spirals. No need to embarrass anybody publicly. Just clarity. And somehow, everywhere we went, people respected him. Even now, they still do.</p><p>I believe it was because people trust his consistency. They know he is fair. They know he is not driven by ego. And they know he holds himself to the same standard he expected from others.</p><p>That kind of leadership leaves an imprint on people. We watched him carefully. And without realizing it, we were learning how grown leaders carry responsibility without losing dignity.</p><h2><strong>The Day My Principal Interrupted Me</strong></h2><p>Nearly ten years ago, I found myself drifting from the standard I had set for myself. I was tired. Burned out before I even fully understood what burnout was. Morale felt low. Resistance felt constant. And if I am honest, frustration had started leaking into my attitude.</p><p>One day, during a conversation with my principal, I caught myself doing something I had always prided myself on avoiding. I stooped into negativity. Not screaming. Not raging. Just enough cynical commentary to sound justified. Enough irritation to feel validated in the moment.</p><p>And before I could continue, she stopped me. Calmly. Quickly. Lovingly.</p><p>&#8220;Stop that. You&#8217;re better than that. As leaders, we don&#8217;t do negativity. We have enough of it in this building that we fight daily.&#8221;</p><p>I still remember how quiet the room felt after she said it.</p><p>Because she did not accuse me.  She did not embarrass me.  She did not question my heart. She reminded me of who she knew me to be.</p><p>And in that moment, she reminded me that leadership demands more from us than simply being &#8220;understandably frustrated.&#8221; Leadership requires emotional discipline. It requires maturity. It requires protecting the climate even when we ourselves are tired of fighting for it.</p><p>That conversation changed me. Not because she was harsh.  But because she cared enough to lovingly interrupt me before negativity became normal.</p><p><em>That</em> is leadership.</p><h2><strong>When the Roles Change</strong></h2><p>Years later, as a building leader, I found myself watching something beautiful happen in our school culture.</p><p>The negativity that once lingered in corners and conversations had slowly started fading year after year. Progress became visible. Systems improved. Morale strengthened. And, if we are honest, a few changes in scenery among key negative voices helped too. (A mentor of mine once described certain people this way: &#8220;They wouldn&#8217;t be happy if you gave them a hundred-dollar check because they&#8217;d have to spend gas money to cash it.&#8221; I laughed then. I still laugh now.)</p><p>But eventually we reached a point where most concerns being voiced were actually healthy ones. Real problems with real solutions.</p><p>We needed more copy paper.  We needed better systems for covering classes when substitutes were unavailable.  We needed operational adjustments-not emotional chaos.</p><p>And then I found myself facing something harder. A staff member I had hired.  Someone I had believed in.  Someone I had advocated for. Over time, they had soured. And in what little &#8220;messiness&#8221; remained in our building-as my grandmother would have called it-their fingerprints seemed connected to nearly every piece of gossip and negativity circulating through recent months. And other members of our staff were being hurt by it.</p><p>And suddenly, I was standing where my principal once stood with me. I was reminded that leaders are called to safeguard culture.</p><p>Not control people.  Not micromanage personalities.  But protect the emotional and professional climate where children and adults are supposed to flourish. That responsibility means we must discern carefully.</p><p>Some concerns are valid and solvable.  Those deserve attention and action. But toxicity? Toxicity spreads. Left unchecked, it poisons trust. It weakens morale. It exhausts good people. And eventually, children feel the weight of adult dysfunction even when we think they cannot see it.</p><p>So the conversation had to happen. And just like the leaders before me, I discovered that the goal was not accusation. It was restoration.</p><p>I reminded this person who they were. Their value. Their gifts. Their future. I reminded them that we are on the same team and working toward the same mission. But I also lovingly drew the line. Because if we are going to lead together, we cannot abandon the responsibility that leadership requires.</p><p>Not for comfort.  Not for popularity.  Not to avoid awkwardness.</p><p>Sometimes love sounds like encouragement.  And sometimes love sounds like accountability.</p><p>Both matter.</p><h2><strong>What This Means for Us</strong></h2><p>As leaders, we cannot become so uncomfortable with conflict that we tolerate what harms culture.</p><p>Children deserve healthy adults.  Schools deserve healthy climates.  And organizations deserve leaders courageous enough to address what threatens both.</p><p>That does not mean becoming harsh. It means becoming honest.</p><p>It means learning how to confront without humiliating.  Correct without condemning.  Lead without retaliating.</p><p>It means understanding that leadership is not measured by how many people like us in easy moments, but by whether we are willing to protect what matters in difficult ones. And perhaps most importantly, it means remembering that accountability begins with us.</p><p>Before we correct others, we must continually examine ourselves.</p><p>Our tone.  Our consistency.  Our integrity.  Our posture.</p><p>Because people can endure hard conversations when they trust the heart behind them.</p><h2><strong>The Heart of the Lesson</strong></h2><p>Healthy leadership requires both grace and boundaries.</p><p>Too much grace without accountability creates chaos.  Too many boundaries without love creates fear.</p><p>But when truth and love walk together, culture changes.</p><p>The strongest leaders are not the loudest people in the room. They are often the calmest. The clearest. The most consistent. The ones who can look at dysfunction without becoming dysfunctional themselves. That is the work.</p><p>To stand firm without becoming hard.  To correct without becoming cruel.  To protect culture without losing compassion. And maybe that is why the milk crate still matters.</p><p>Because somewhere along the way, many of us learned leadership by watching ordinary people quietly hold standards without losing their humanity.</p><p>That kind of leadership still builds lives.</p><h2><strong>Reflection for the Week</strong></h2><p>This week I&#8217;ll be holding a few reflection questions near to my heart. I hope you do too:</p><ol><li><p>What issues in our organization have I avoided addressing simply because the conversation feels uncomfortable?</p></li><li><p>Am I discerning the difference between temporary frustration and true toxicity?</p></li><li><p>When I correct others, do people experience my leadership as restorative or retaliatory?</p></li><li><p>Have I unintentionally allowed negativity to become normalized in spaces I lead?</p></li><li><p>How can I hold clearer boundaries while still leading with compassion and dignity?</p></li></ol><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong>A Continued Invitation</strong></h2><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h2><strong>Recognition</strong></h2><p>This week&#8217;s reflection belongs first to the quiet leaders who taught us that strength does not always raise its voice.</p><p>To my father, thank you for teaching us that integrity speaks loudest through consistency. Thank you for showing us how to draw lines without losing composure, and how to stand firm without becoming unkind.</p><p>To the principal who interrupted my negativity years ago, thank you for loving me enough to correct me quickly. Your words still echo in my leadership today.</p><p>To the mentors, teachers, administrators, custodians, secretaries, coaches, bus drivers, and support staff who protect school culture every single day-often through unseen conversations and uncomfortable moments-thank you for choosing courage over convenience.</p><p>And to the milk crate, thank you for reminding us that leadership was never about power.</p><p>It was always about responsibility.</p>]]></content:encoded></item><item><title><![CDATA[The Sacrifices We Don't Always Fully Understand]]></title><description><![CDATA[A Mother's Day Reflection]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/the-sacrifices-we-dont-always-fully</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/the-sacrifices-we-dont-always-fully</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 09 May 2026 13:01:23 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/416cc3f5-315b-40a9-8a26-0de90ae00f9e_1448x1086.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>This week&#8217;s reflection did not begin on an old milk crate.</p><p>It did not rise from a lesson learned sitting in a school hallway, listening to elders tell stories between basketball games, or the ordinary traffic of school life.</p><p>This one found me standing quietly in the doorway of my own home. Watching and remembering.</p><p>Reflecting on the kind of sacrifice that was so present when I was a child, so constant, so woven into the rhythm of everyday life, that I did not have the maturity to recognize it for what it was. (Isn&#8217;t it funny how adulthood changes your eyesight-as children, we notice what our parents provide. As adults-especially after becoming parents ourselves-we finally begin to understand what it cost them to provide it.)</p><p>Some sacrifices are loud. Most are not.</p><p>Most come wrapped in grocery bags, doctor&#8217;s appointments, sleepless nights, unpaid bills, postponed dreams, and prayers whispered from tired bodies before the sun comes up.</p><p>And somewhere between raising children, paying bills, surviving difficult seasons, and trying to become decent human beings ourselves, we begin to recognize the sacred weight our mothers carried all along.</p><p>This reflection is for them.</p><p>For the mothers whose sacrifices rarely made announcements. For the women who quietly gave pieces of themselves so their children could become whole. For the mothers in our homes, in our schools, in our churches, and in our communities whose love has so often been measured not by what they received, but by what they were willing to give.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!MS-P!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!MS-P!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!MS-P!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!MS-P!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!MS-P!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!MS-P!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/197003328?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!MS-P!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!MS-P!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!MS-P!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!MS-P!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F7dc59a19-b591-42d5-9f87-eb5ead06df46_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2>Disclaimer: What This Week Is Not</h2><p>Before going further, let me offer a brief disclaimer about what this reflection is not:</p><p>This is not an attempt to romanticize suffering. It is not a declaration that motherhood only matters if it involves pain and sacrifice. And it is certainly not meant to overlook the many forms family takes or the many women who step into maternal roles through love, sacrifice, mentorship, adoption, fostering, teaching, coaching, and caregiving (this week is for all of you too). Because some of the most formative maternal voices in our lives never gave birth to us, but helped raise us just the same-professionally, spiritually, emotionally, and educationally.</p><p>This is simply an acknowledgment. An acknowledgment that many mothers carry burdens we do not fully understand until years later. Sometimes not until we are standing in their shoes ourselves.</p><p>Sometimes not until we are standing in our own kitchen, holding our own child, looking back through the front door of memory and realizing, &#8220;Wow&#8230;she carried more than I ever knew.&#8221;</p><h2>The First Sacrifice</h2><p>My mother&#8217;s sacrifice began long before I was born.</p><p>As a child, she was diagnosed with a degenerative musculoskeletal disease. For a season of her young life, she spent nearly a year alone in a Shriners Hospital several counties away from her family, recovering while most children her age were learning multiplication tables, riding bicycles, and running through the yard without thinking about the blessing of movement.</p><p>Doctors eventually told her something devastating: she would likely never have children. And if she attempted to, pregnancy could significantly worsen the progression of her disease and permanently impact her health.</p><p>But even then, before titles, careers, accomplishments, and adult responsibilities, her dream was simple: she wanted to be a <em>mother</em>.</p><p>Not for applause. Not for recognition. Not because motherhood looked easy. But because somewhere deep in her spirit, she believed nurturing a family was her purpose.</p><p>(As adults, we might call that life purpose. As a child, she probably just called it a dream.)</p><p>Years later, she made the decision to give me life, knowing full well what it might cost her physically. She chose motherhood knowing it could come at the expense of her own body, her own comfort, and her own quality of life.</p><p>And like so many great mothers, the sacrifice did not end in the delivery room. In many ways, it only began there.</p><p>There were vacations postponed. Wants shelved. Comforts delayed. Dreams rearranged.</p><p>She stayed home to raise her children when it would have been easier financially not to. She made the needs of her family the center of her daily work.</p><p>I still remember her taking odd jobs here and there to afford &#8220;<em>Hooked on Phonics</em>&#8221; cassette tapes because she wanted her son reading before I ever stepped into kindergarten. She found ways to pay for a strong preschool education even when resources were limited.</p><p>(At the time, I thought those things simply appeared. Children usually do.)</p><p>We do not always see the math our parents are doing behind the scenes. We do not see the sacrifices hidden between utility bills and grocery lists. We do not hear every quiet conversation about what can wait and what cannot. We do not understand the holy calculation of, &#8220;I can go without if it helps my child have more.&#8221;</p><p>Then, twelve years later, approaching forty years old and fully aware of what another pregnancy would mean physically, she made the sacrifice again and gave life to my younger brother.</p><p>The physical cost was real. The risk was real. The decline she knew might come faster was real.</p><p>But so was her love. And the giving never stopped. Years later, it still has not stopped.</p><p>Now the family is larger. A daughter-in-law. Three grandchildren. More birthdays. More school programs. More needs. More opportunities to give pieces of herself away in the name of love.</p><p>And she still does. Without complaint. Without keeping score. Without demanding repayment.</p><p>Just love. The kind of love children rarely understand in real time.</p><p>I truly believe one of the great awakenings of adulthood is this: a child often cannot fully appreciate the sacrifice of their parents until they become parents themselves. Because parenthood has a way of translating memories:</p><ul><li><p>What once looked like routine becomes sacrifice</p></li><li><p>What once looked like responsibility becomes love.</p></li><li><p>What once looked like &#8220;just what mothers do&#8221; becomes something sacred.</p></li></ul><h2>Watching Sacrifice Up Close</h2><p>Ten years ago, I witnessed motherhood from a different seat. Not as a son. But as a husband.</p><p>When my wife gave birth to our first son, I witnessed firsthand the physical and emotional sacrifices motherhood demands. I watched postpartum depression enter our home quietly, without warning, without an instruction manual, and without nearly enough conversation from the outside world about how heavy those moments can feel. </p><p>There are some battles mothers fight that nobody sees clearly from the outside. They may be holding a baby and still feel like they are trying to hold themselves together. They may be smiling in pictures while silently trying to find their way back to peace.</p><p>And I watched the woman I love sacrifice not only her body, but parts of her emotional strength, her rest, her sense of normalcy, and still continue to love our child with everything she had.</p><p>Two years later came our second son. Only this time, there were complications.</p><p>Early labor. An emergency C-section. Then months of recovery complicated by a MRSA infection in the surgical site.</p><p>I remember watching her attempt to heal while simultaneously nurturing a newborn who still needed his mother every hour of the day. That kind of grit humbles you as a man. (Do any of us men know what <em>real</em> pain really is?) Because mothers often do not get the luxury of recovering in silence.</p><p>Healing still has to happen while someone is crying. Pain still has to be managed while diapers need changing. Exhaustion still has to move over because a newborn does not understand that mama is hurting too.</p><p>Then came endometriosis. More pain. More procedures. More uncertainty. Doctors suggested another pregnancy would likely be difficult. But determined to have one more child, three years later our third son arrived.</p><p>And once again, the sacrifice continued.</p><p>Now, there is another layer to this story that mothers in education know all too well. My wife is a teacher. And teachers understand something many outside education never fully see: there is no pause button on responsibility simply because life changes.</p><p>So during each pregnancy, she worked right up until the final possible moment. Not because it was easy. Not because her body was not tired. Not because standing, walking, teaching, planning, grading, communicating, and managing a classroom while carrying life was simple. She did it because every day used before delivery meant one fewer day available afterward for recovery and bonding with our children.</p><p>No extended paid leave waiting in abundance. No magical reserve of extra time. No system that fully accounts for the physical, emotional, and financial reality of becoming a mother. Just sacrifice.</p><p>Working while exhausted. Standing while hurting. Teaching while carrying life. Smiling while counting days. Then recovering for months with reduced or absent pay because motherhood still costs women professionally in ways we rarely discuss honestly enough. And yet she kept showing up. For her students. For our children. For our family.</p><p>That kind of sacrifice deserves more than a social media post once a year. It deserves recognition. It deserves reflection.</p><p>And for those of us entrusted with leadership, it deserves a response.</p><h2>The Mothers Carrying Schools</h2><p>This Mother&#8217;s Day weekend, I want to especially recognize the mothers working in education. Because the work they carry is sacred in ways statistics can never fully measure.</p><p>Every day, mothers in schools pour maternal care not only into their own children, but into dozens, sometimes hundreds, of children who walk through their classrooms, offices, cafeterias, hallways, and buses carrying unseen burdens.</p><p>Some children arrive needing instruction. Others arrive needing stability.</p><p>Some need encouragement. Some need correction. Some need food. Some need patience. Some need grace. Some simply need one adult who sees them.</p><p>And so many educators, especially mothers, become far more than teachers.</p><p>They become caregivers. Nurses. Counselors. Protectors. Advocates. Safe places.</p><p>For some students, the teacher standing at the classroom door may be the closest thing to consistent maternal love they experience all day. That is not in the job description. But it is in the work.</p><p>And after carrying everyone else&#8217;s children emotionally for eight or ten hours, many mothers go home and begin another shift with their own families.</p><p>Homework. Dinner. Laundry. Practice. Baths. Bedtime prayers. Packing lunches. Signing folders. Answering emails after everyone else is asleep. </p><p>All while fighting exhaustion and wrestling with the quiet guilt so many working mothers carry-the feeling that no matter how much they give, they still wish they could give more.</p><p>Then there are the sacrifices unique to education itself. Working until the final days before delivery to preserve leave. Returning before fully healed because finances demand it. Missing moments with their own children because someone else&#8217;s child needed them. Pouring energy into classroom celebrations, field trips, graduations, testing seasons, parent conferences, and emotional student needs, then wondering whether they had enough left to give at home.</p><p>These are not small things. These are daily acts of love. And too often, society praises them without truly supporting them.</p><p>We call mothers strong, but sometimes we use their strength as an excuse not to lighten the load. We call educators heroes, but sometimes we rely on heroism to cover gaps that better systems should address. We celebrate resilience, but sometimes we forget that resilience should be honored, not exploited.</p><p>And that is where the reflection becomes more than personal. That is where it becomes professional. That is where it becomes leadership.</p><h2>What This Means for Us</h2><p>As leaders, Mother&#8217;s Day weekend should do more than move us emotionally.</p><p>It should examine us organizationally. Because appreciation without awareness can become shallow. Gratitude without action can become performance. And recognition without reflection can become just another paragraph in an email.</p><p>If we are going to honor mothers in education, then we must be willing to ask harder questions about the cultures we lead.</p><p>Do the mothers in our schools feel seen as whole people?</p><p>Do they feel supported when life changes?</p><p>Do they feel safe enough to name exhaustion without being judged as less committed?</p><p>Do they feel permission to care for their own families without guilt?</p><p>Do our systems honor the humanity of the people we ask to serve children every day?</p><p>Because leadership is not merely about producing outcomes. Leadership is stewardship.</p><p>Stewardship of students, yes. Stewardship of instruction, yes. Stewardship of mission, yes. But also stewardship of the adults who make the mission possible.</p><p>If we want educators to build lives of excellence, then we must build environments where they can serve with excellence without being emptied. If we want educators to live with purpose, then we must honor the full humanity of that purpose, including the sacred responsibilities they carry at home. If we want integrity, then we must be honest about the cost of the work and courageous enough to improve the systems around those who sacrifice most.</p><p>That is leadership. Not title. Not position. Not volume.</p><p>Leadership is the willingness to see what others are carrying and ask, &#8220;How can I help make the load lighter?&#8221;</p><h2>The Heart of the Lesson</h2><p>The older I become, the more I realize sacrifice is not only a family value. It is a leadership value.</p><p>In education, sacrifice shows up every day in ways that rarely make headlines. It appears in the teacher who stays late to call a parent. It appears in the administrator who absorbs criticism so a teacher can keep teaching with confidence. It appears in the staff member who notices a hungry child, a tired colleague, or a family quietly struggling and decides, without announcement, to do something about it.</p><p>That is leadership. Not the kind that needs a microphone. The kind that notices. The kind that serves. The kind that carries responsibility with love.</p><p>And on Mother&#8217;s Day weekend, I cannot help but think about the mothers in our schools who understand this kind of leadership deeply. They carry the sacred weight of their own families, then walk into classrooms and offices prepared to carry the weight of other people&#8217;s children too.</p><p>That kind of service should shape how we lead.</p><p>Because if we are honest, schools do not become excellent simply because of strategic plans, test scores, initiatives, or carefully written mission statements. Schools become excellent when people are willing to give of themselves for something larger than themselves.</p><p>But here is the responsibility for leaders: we cannot celebrate sacrifice while ignoring support. We cannot praise mothers for their endurance and fail to examine the systems that require so much of it. We cannot applaud resilience while overlooking exhaustion. We cannot honor commitment while pretending the cost is invisible.</p><p>Leadership must do more than admire sacrifice. Leadership must protect the people who are sacrificing.</p><p>That means creating schools where mothers are seen not only as professionals, but as whole people. It means building cultures where educators can serve with excellence without losing themselves in the process. It means recognizing that the strongest schools are not built by draining good people dry, but by sustaining them so they can keep pouring into children with joy, health, and purpose.</p><p>Because sacrifice without support eventually becomes depletion. And depletion is not the same as devotion.</p><p>So the lesson for us as leaders is clear:</p><ul><li><p>Honor the sacrifice, but do not exploit it.</p></li><li><p>Recognize the calling, but do not romanticize the cost.</p></li><li><p>Celebrate the mothers, teachers, caregivers, and servant-leaders among us, but also ask what we are doing to make their load lighter.</p></li></ul><p>That is how we build lives of excellence. That is how we lead with purpose. That is how we practice integrity. Not merely by saying thank you once a year, but by shaping schools and communities where the people who give the most are also cared for with intention, dignity, and grace.</p><p>And if that kind of leadership does not deserve an amen from the corner, I do not know what does.</p><h2>Reflection for the Week</h2><p>This week, I&#8217;m compelled to hold a few questions near to my heart:</p><ol><li><p>As leaders, where have we benefited from the quiet sacrifices of others without fully recognizing the cost?</p></li><li><p>How can we move beyond praising sacrifice and begin creating systems that better support the people who consistently give of themselves?</p></li><li><p>In what ways are the mothers and maternal figures in our schools carrying emotional, professional, and personal burdens that may go unseen?</p></li><li><p>Are we building a culture where educators can serve children with excellence without feeling guilty for also caring for their own families?</p></li><li><p>What practical step can we take this week to lighten the load for a mother, teacher, caregiver, or colleague who has been carrying more than we realized?</p></li></ol><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h3><strong>A Continued Invitation</strong></h3><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h2>Recognition</h2><p>This week, I honor my mother.</p><p>For every sacrifice seen and unseen. For every prayer whispered quietly. For every dream postponed so her children could pursue their own. For every moment she gave from a body already carrying pain, and every act of love that shaped me before I had the words to call it sacrifice.</p><p>I honor my wife.</p><p>For her strength, resilience, sacrifice, and unwavering devotion to our children, even in seasons that demanded more than words can properly capture. I honor the pregnancies, the recoveries, the complications, the pain, the teaching days that stretched beyond exhaustion, and the love that kept showing up anyway.</p><p>I also honor my mentor.</p><p>Who carried a mothering spirit into every space she led. In many ways, she helped raise many of us professionally. She corrected us, encouraged us, challenged us, covered us, and taught us how to carry ourselves with purpose and integrity. And across her career as a teacher and principal, she helped raise thousands of children-not only through instruction, but through presence, expectation, discipline, compassion, and love. (And those of us who have been shaped by that kind of leadership know the difference it makes.)</p><p>And I honor the mothers working in education.</p><p>The women carrying classrooms and households simultaneously. The women nurturing futures while often neglecting their own exhaustion. The women whose influence stretches far beyond lesson plans and report cards. The women who teach, comfort, correct, encourage, advocate, protect, and then go home and keep loving some more.</p><p>Your sacrifice matters. More importantly, your sacrifice is shaping lives.</p><p>And this week, before the noise of the world rushes back in, I simply wanted to say what many of us probably do not say enough:</p><p>Thank you.</p><p>Thank you for the love we saw. Thank you for the sacrifices we missed. Thank you for the strength we benefited from before we understood its cost.</p><p>And somewhere beyond these words, beyond these memories, beyond these reflections from the front door of home itself, I imagine the old milk crate sitting quietly in the corner, smiling in approval.</p><p>Because even there, long ago, the first lessons about sacrifice were already being taught.</p><p>This week, honor the sacrifice.</p><p>Notice the mother who is tired but still showing up. Thank the mentor who helped raise you professionally. Support the educator who is carrying both her classroom and her home. Lighten the load for someone who has spent years carrying more than most people ever saw.</p><p><strong>It matters more than you know.</strong></p>]]></content:encoded></item><item><title><![CDATA[Making Time to Celebrate]]></title><description><![CDATA[When the Weight Is Real But the Wins Are Too]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/making-time-to-celebrate</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/making-time-to-celebrate</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 02 May 2026 13:31:16 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/f2ed2bcb-5f85-46c6-a388-3cc8f0770239_1448x1086.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>There are some lessons that do not come to us in polished conference rooms, printed leadership manuals, or neatly packaged professional development slides.</p><p>Some lessons come while sitting on an <a href="https://lessonsfromthemilkcrate.substack.com/p/lessons-from-the-milk-crate">old milk crate</a>.</p><p>Not because the milk crate was impressive. It was not. It was ordinary. Scuffed up. Utilitarian. Probably holding more stories than it ever held milk. But that is often where leadership forms us best: not in the places designed to impress us, but in the places humble enough to teach us.</p><p>And this week, I find myself returning to that milk crate with a simple but necessary reminder:</p><p>We have to make time to celebrate. Not because the work is finished. Not because every problem is solved. Not because resistance has disappeared, criticism has quieted, or the weight of leadership has suddenly lifted.</p><p>But because celebration is not the denial of the weight.</p><p>Celebration is how we remember the work is not in vain.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!sMq4!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!sMq4!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!sMq4!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!sMq4!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!sMq4!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!sMq4!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/i/196215509?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F55cf8fc2-d782-41ea-b583-27f29575a061_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" 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class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3>Disclaimer: What This Week Is Not</h3><p>Let me say this carefully:</p><p>This week is not about pretending leadership is easy. </p><p>It is not about ignoring the emotional cost of carrying people, systems, expectations, disappointments, fears, conflict, grief, criticism, dysfunction, defiance, unease, and uncertainty.</p><p>It is not about acting as though leaders do not sometimes sit quietly in their cars before walking into the building, asking God for just enough strength to carry what they cannot say out loud.</p><p>Because leadership is heavy.</p><p>The buck stops with leaders. And while others may get to clock out, shut the laptop, silence the phone, and mentally step away, leadership rarely gives us that luxury. We may leave the building at 4:00, but the burden does not always leave with the building. We may wake up on Saturday morning, but the weight has a way of waking up with us.</p><p>We carry staff through seasons of joy and sorrow. We carry teams through uncertainty. We carry families through frustration. We carry the organization through moments when people cannot yet see what we are trying to build.</p><p>And, if we are honest, leadership may be one of the most emotionally draining responsibilities a person can carry.</p><p>So no, this week is not about minimizing the weight.</p><p>This week is about remembering that even while carrying the weight, we must not miss the wins.</p><h3>The Christmas Trash Bag</h3><p>Now, I know summer is nearly here. But as of this writing, we are only about 34 weeks away from Christmas, so I feel perfectly justified bringing up wrapping paper, Christmas lights, and the sacred calling of fathers everywhere: holding the trash bag beside the tree. (You know the scene.)</p><p>The children are opening gifts with wonder in their eyes. The Christmas music is playing. Somebody has coffee. Somebody has a camera. Somebody has already lost the instructions to a toy that requires batteries no one bought.</p><p>And there is Dad. Standing nearby. Trash bag in hand. Waiting. Not watching the gift. Not watching the joy. Watching the wrapping paper hit the floor.</p><p>I became that dad. But before I became that dad, I was a child who experienced Christmas very differently.</p><p>As a child, my mother kept an immaculate home - the kind of house where people said, &#8220;You could eat off the floor,&#8221; and in her case, you probably could have (she still keeps it this way). I do not remember the smell of fancy candles or plug-ins. I remember <em>Comet</em>. That was the fragrance of order in our house. </p><p>Christmas mornings were slow. Unhurried. My parents and I would exchange gifts, have breakfast, and spend time together. Yes, there were grandparents to visit and cousins to see, but the morning itself was not rushed. My parents allowed me to experience the fullness of the holiday.</p><p>They gave me presence more presents. Presence. They let me play. They watched. They laughed. They made room for joy to settle in the room before we hurried off to the next place.</p><p>Then my wife and I had children of our own.</p><p>Our first son came, and then our second just two years later, and like many young parents, we tried to make Christmas magical by making sure we did not miss anything. We woke up at 5:00 or 6:00 in the morning. Coffee. Breakfast. Gifts. Christmas movies. A few minutes to play. Then hurry up and get dressed because we had to make it to the grandparents by brunch. Then play quickly. Then pack up. Then on to the next house.</p><p>We were trying to give our children everything. But in trying to give them everything, we were rushing them through the very thing that mattered most.</p><p>By the time our boys were old enough to notice (maybe four or five years old ) my wife and I began reflecting on our own childhood experiences. And somewhere in that reflection, we realized we had become so focused on moving to the next thing that we were barely making time to celebrate the thing right in front of us.</p><p>So we pivoted. We slowed the holiday down. We stopped rushing the morning. We made space for joy. We made time for presence. (Now, let me be clear. That did not mean the Christmas tree stayed up until April. There is a difference between celebrating a season and living in one past its purpose. We cannot stay so long in celebration that we become comfortable, and we cannot become so comfortable that we go stale.)</p><p>We have to stop long enough to let gratitude do its work.</p><p>We have to make time to celebrate.</p><h3>Back on the Milk Crate</h3><p>Years ago, I found myself sitting on the milk crate with a few teammates while we waited on late buses to pick up students.</p><p>It had been one of <em>those</em> seasons. The kind where the work was showing evidence of progress, but the atmosphere did not yet feel like progress. Preliminary data suggested we had turned a corner. Test scores were rising. Graduation rates had improved significantly. Disciplinary infractions were down compared to previous years.</p><p>On paper, we were better. In the data, we were better. By many measurable indicators, we were significantly better than what we had inherited.</p><p>And yet the climate in the building told another story. We were tired. Burnt out from the work. Worn down by conflict. Frustrated by resistance. Discouraged by the gap between what the evidence showed and what some people still perceived. (Sometimes data tells one story while perception tells another. And if we are not careful, misperception can become louder than truth.)</p><p>I remember sitting there, falling into that trap myself. &#8220;Yes, we doubled the pass rate,&#8221; I said, &#8220;but that is not good enough. We need to change&#8230;&#8221;</p><p>And before I could keep charging ahead into the next improvement plan, the next adjustment, the next strategy, a mentor kindly interrupted.</p><p>Not harshly. Not with accusation. But with wisdom.</p><p>She said, &#8220;If we do not take the time to slow down, recognize our wins, and actually celebrate them, then why should the people we lead?&#8221;</p><p>That sentence stayed with me.</p><p>Because she was right.</p><p>As an early leader, I was always thinking about what was next. The next gap. The next goal. The next problem. The next plan. The next hill to climb.</p><p>And without realizing it, I was teaching the culture to do the same. We were acknowledging progress, but we were not celebrating it. We were noting improvement, but we were not honoring the people who helped make it happen. We were so focused on the next mountain that we forgot to look back and celebrate the mountain we had already climbed.</p><p>That day, on the milk crate, I learned something leaders cannot afford to forget:</p><p>Uncelebrated progress eventually feels like invisible labor.</p><p>And invisible labor wears people down.</p><h3>The Lesson Revisited</h3><p>Years later, as a school leader, I found myself in a similar season.</p><p>We were three or four years into the work. New administrators were juggling the delicate balance of leading while learning, serving while assimilating, and carrying responsibility while still finding their footing.</p><p>By April, the weight was on all of us. The resistance to change. The unease. The unknown. The long days. The hard conversations. The pressure of state testing. The final push for review and fine-tuning. Promotion and retention decisions. End-of-year ceremonies. Staffing for the next year. Planning for the next season while still trying to survive the current one.</p><p>Everything came at once.</p><p>And in those moments, even strong leaders can find themselves asking quiet questions: Are we making a difference? Is this worth it? Why does it still feel so hard if things are actually getting better? Why are we still facing resistance when the evidence says progress is real?</p><p>And then, almost right on time, the data began to show what the daily emotions had made difficult to see.</p><p>Staffing was no longer the same problem it had been. We were nearly fully staffed for the next year, which suggested something important: people actually wanted to join the cause.</p><p>Discipline was improving. Attendance was in a better place. Achievement data was not just slightly better. It was remarkably better.</p><p>The work was working.</p><p>But we were so tired from carrying it that we almost missed the evidence right in front of us. And in that moment, I was called back to the milk crate.</p><p>Not physically, but spiritually. I went back to that old lesson. Back to that mentor&#8217;s voice. Back to the reminder that if leaders do not slow down and celebrate the wins, the people we lead may never know how much their effort mattered.</p><p>So I took my team back with me. Back to the milk crate. Not for a lecture. Not for another meeting. Not for another initiative. But simply to celebrate.</p><p>Even if only for a moment.</p><p>Because sometimes a moment is enough to remind weary people that the work is not wasted.</p><h3>What This Means for Us</h3><p>As leaders, we cannot live in celebration forever.</p><p>We cannot set up camp in yesterday&#8217;s success and expect tomorrow&#8217;s challenges to solve themselves. Getting too comfortable can lead to complacency. Complacency can lead to decline. And decline often begins quietly, while everyone is still admiring what used to be.</p><p>But the opposite danger is just as real. We can become so committed to improvement that we never let gratitude interrupt our urgency. We can become so disciplined about what is next that we fail to honor what has already been accomplished. We can become so focused on the people resisting change that we forget to celebrate the people carrying change.</p><p>That is dangerous.</p><p>Because people need to know their work matters. Teachers need to know their work matters. Staff need to know their work matters.</p><p>Assistant principals, counselors, secretaries, custodians, cafeteria workers, bus drivers, instructional assistants, coaches, mentors, and every person who contributes to the life of a school need to know their work matters.</p><p>Celebration is not fluff. Celebration is fuel.</p><p>It reminds the organization that progress is possible. It reminds weary people that their effort is seen. It reminds the team that while the work is not finished, the work is making a difference.</p><p>And sometimes, that reminder is the difference between burnout and renewed belief.</p><h3>The Heart of the Lesson</h3><p>Here is the heart of it.</p><p>Leadership will always carry weight. We carry what others cannot see. We carry what others do not know. We carry decisions, disappointments, tensions, transitions, and the emotional weather of the organization.</p><p>But carrying the weight does not mean we must ignore the wins.</p><p>In fact, because the weight is so real, the wins must be celebrated with intention.</p><p>We do not celebrate because everything is perfect. We celebrate because progress is sacred. We celebrate because people gave effort. We celebrate because teams endured. We celebrate because the data tells a story that fatigue sometimes tries to silence. We celebrate because the people who helped move the work forward deserve more than a passing acknowledgment.</p><p>They deserve a pause. A word. A moment. A thank you.</p><p>A reminder that their labor was not invisible.</p><p>Because if we never stop to celebrate, people may begin to believe that nothing is ever enough. And when people believe nothing is ever enough, discouragement starts dressing itself up as professionalism.</p><p>So we pause. Not forever. But faithfully.</p><p>We pause long enough to say, &#8220;Look how far this team has come.&#8221;</p><p>We pause long enough to say, &#8220;This mattered.&#8221;</p><p>Then we pick the work back up. Not because the work stopped being heavy.</p><p>But because celebration gave us enough strength to carry it again.</p><h3>Reflection Questions for the Week</h3><p>This week, as (still) an imperfect leader, I am compelled to hold a few questions near to my heart:</p><ol><li><p>What recent win have I acknowledged privately but failed to celebrate publicly?</p></li><li><p>Who helped make progress possible, and how can I intentionally honor their contribution?</p></li><li><p>Have I allowed resistance or misperception to become louder in my mind than the evidence of growth?</p></li><li><p>Where might my urgency for what is next be preventing my team from feeling gratitude for what has already been accomplished?</p></li><li><p>How can I create a rhythm of celebration that fuels the work without allowing us to become complacent?</p><p></p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p></li></ol><h3><strong>A Continued Invitation</strong></h3><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h3>Recognition</h3><p>This week, I am grateful for the mentors who loved me enough to interrupt my momentum with wisdom. I am grateful for the teammates who have sat beside me in weary seasons and reminded me that leadership was never meant to be carried alone. I am grateful for the staff members who keep showing up, keep serving children, keep believing in growth, and keep helping build lives of excellence, purpose, and integrity.</p><p>I am grateful for my wife and our children, who continue to teach me that presence is often the greatest gift we can give. And for my parents who taught me that lesson first. After all, the memories made outlast any material gift we can give.</p><p>And I am grateful for that old milk crate - that humble seat of reflection - where I learned that leadership is not only about carrying the weight.</p><p>It is also about making time to celebrate the grace that helped us carry it.</p><p><strong>This week, make time to intentionally celebrate.</strong></p><p><strong>It matters more than you know.</strong></p>]]></content:encoded></item><item><title><![CDATA[You Can't Drift Apart When It Matters Most]]></title><description><![CDATA[Why the Pressure to Perform Is the Exact Moment Teams Must Pull Together]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/you-cant-drift-apart-when-it-matters</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/you-cant-drift-apart-when-it-matters</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 25 Apr 2026 16:01:33 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/1938864c-3a59-4d45-9c19-1ff6429120d0_2000x1545.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>We&#8217;re back!</p><p>Spring break is long gone and Summer break is still out of reach. I hope you are well-rested. And if you&#8217;re not, testing season is here whether we&#8217;re ready or not. So let&#8217;s dig in for a final stretch. </p><p><em>This</em> is that stretch.</p><p>The stretch where everything matters. The stretch where the work intensifies. The stretch where everyone has a role to play, and the pressure to perform begins to rise.</p><p>And if we&#8217;re not careful, this is also the stretch where teams begin to drift.</p><p>Not because we don&#8217;t care. Not because we aren&#8217;t committed. But because we get busy-we focus on our part. We narrow our lane. We try to carry what&#8217;s ours as efficiently as possible. And slowly, quietly, we begin to separate.</p><p>That&#8217;s why we come back to the crate.</p><p>Not for nostalgia, but for alignment. Not to slow the work,but to steady how we carry it.</p><p>Because the milk crate has always been a place where we remember something simple, but essential:</p><p>We were never meant to do this alone.</p><p>And if there&#8217;s ever a time to hold onto that truth, it&#8217;s now.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!9XsA!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!9XsA!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!9XsA!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!9XsA!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!9XsA!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!9XsA!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg" width="1024" height="1024" 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srcset="https://substackcdn.com/image/fetch/$s_!9XsA!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!9XsA!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!9XsA!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!9XsA!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F80902dca-264b-4763-89ca-89d45a9e9c61_1024x1024.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>Disclaimer: What This Week Is Not</strong></h3><p>Let&#8217;s be clear about something:</p><p>This week is not about lowering expectations. It is not about excusing underperformance. It is not about avoiding accountability or simply &#8220;getting along.&#8221;</p><p>This is not a call to relax the standard. It is a call to protect the connection. Because in seasons like this, we often convince ourselves that the best way to get more done is to go at it alone.</p><p>We divide the work. We assign the roles. We spread out. And somewhere in that process, without intention, we begin to drift.</p><p>Now hear this clearly: there are always gaps to address. There are always areas for growth. And there are moments when we must speak directly to inconsistency with clarity and courage.</p><p>But this week is not about chasing every gap.</p><p>It&#8217;s about making sure that in the midst of the work, we don&#8217;t lose <em>each other</em>.</p><p>Because when teams drift apart, stress doesn&#8217;t decrease-it multiplies.</p><p>And that quiet drift is where this week&#8217;s lesson begins.</p><h3><strong>When Teamwork Comes Naturally</strong></h3><p>A few months ago, I found myself standing on the sideline of a youth soccer field, watching my seven year-old play for the first time.</p><p>Some of the kids knew the game. Some didn&#8217;t. My son had never played but he jumped right in. And what stood out to me wasn&#8217;t the skill.</p><p>It was the way they all played <em>together</em>.</p><p>These were children-most of them strangers to one another-and yet teamwork came naturally.</p><p>When someone fell, they rushed over to help them up.  When someone got hurt, they took a knee and bowed their heads. When that player stood back up, they cheered like it was the moment that mattered most.</p><p>They encouraged effort. They celebrated one another. They stayed connected.</p><p>And I found myself wondering: When did we (as in us-the grown-folks) lose that?</p><p>When did collaboration become something we had to intentionally <em>relearn</em>?</p><p>Because somewhere along the way, we didn&#8217;t lose the ability to work together, we just drifted away from it.</p><p>And that thought carried me back to a lesson I first learned on the milk crate.</p><h3><strong>A Milk Crate Reset</strong></h3><p>There was a season, much like this one, when everything was happening at once:</p><p>State testing. Finalizing Grades. Awards Programs. Prom. Class Day. Graduation. Preparations for the next year. </p><p>Our team was busy. Productive. Moving. But we were also <em>separate</em>.</p><p>Everyone was handling their responsibilities. Everyone was carrying their load. But we were doing it in isolation-working hard, but not necessarily working <em>together</em>.</p><p>Until one afternoon, something unplanned happened. We all ended up at the milk crate.</p><p>Bus duty. No agenda. No structure. Just presence.</p><p>And in that moment, we started talking-not about tasks, but about what we were carrying. And something shifted:</p><p>One person said, &#8220;I can help with that.&#8221;<br>Another said, &#8220;I&#8217;ve got something that might make that easier.&#8221;<br>Ideas turned into support. Support turned into shared responsibility.</p><p>What felt overwhelming alone became manageable together.</p><p>It wasn&#8217;t a new initiative. It was a reset: a return to each other.</p><p>And as I would later learn, that lesson doesn&#8217;t just belong to the past-it shows up right when we need it most.</p><h3><strong>When Leadership Feels Heavy</strong></h3><p>Recently, my team and I found ourselves in that same kind of season.</p><p>The work was clear. The goals were set. Everyone had a role to play. We were all playing our roles well.</p><p>So we did what leaders often do: we organized, delegated, and dispersed.</p><p>&#8220;Here&#8217;s your assignment. Here&#8217;s your lane. Let&#8217;s move.&#8221;</p><p>And on the surface, it worked. But underneath, something else was happening.</p><p>Stress levels rose. Communication slowed. And without realizing it, we began working around each other instead of with each other.</p><p>It wasn&#8217;t intentional. It was just&#8230;pressure.</p><p>Until we paused. Back in the data room, we reflected. And what we realized was simple, but significant: we weren&#8217;t alone but we were operating like we were.</p><p>So we reset. We reconnected. We talked-not just about tasks, but about capacity. We supported-not just in words, but in action.</p><p>Because even though responsibilities had been divided, the work was never meant to be disconnected.</p><p>And that realization reframed everything.</p><h3><strong>What This Means for Us</strong></h3><p>As we move through this season, especially as leaders, we have to be intentional.</p><p>Not just about what gets done but about how we stay connected while doing it. Because the truth is, pressure has a way of pulling teams apart if we let it.</p><p>People get focused. Time gets tight. Communication becomes transactional.</p><p>And before we know it, we&#8217;ve created distance in a moment that actually requires proximity.</p><p>So this is the work:</p><ul><li><p>Check in.</p></li><li><p>Slow down just enough to reconnect.</p></li><li><p>Create space (even briefly) for people to share what they&#8217;re carrying.</p></li></ul><p>Because sometimes the most effective move in a high-pressure season is not to push harder. It&#8217;s to pull closer.</p><h3><strong>The Heart of the Lesson</strong></h3><p>We assign tasks because the work is big. But we stay connected because the work is shared.</p><p>And when we forget that =, we don&#8217;t just lose efficiency, we lose alignment. We lose support. We lose each other.</p><p>The strongest teams are not the ones where everyone simply does their part. They are the ones where everyone knows that they don&#8217;t have to do it alone.</p><h3><strong>Reflection for the Week</strong></h3><p>This week let&#8217;s hold a few questions close to our hearts:</p><ul><li><p>Where have we unintentionally started working in isolation?</p></li><li><p>Who on our team might be carrying more than we realize?</p></li><li><p>When was the last time we paused&#8212;not to plan&#8212;but to reconnect?</p></li><li><p>Are we leading tasks&#8230; or are we leading people through the work?</p></li></ul><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h3><strong>A Continued Invitation</strong></h3><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share <a href="https://returningtothemilkcrate.substack.com/">here</a>.</p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><h3><strong>Recognition</strong></h3><p>This week, I am grateful for the teams who keep showing up-especially when the work is heavy.</p><p>For the educators who carry responsibility with care. For the leaders who recognize when it&#8217;s time to pause and bring people back together. For those who remind us through action that this work is better when it&#8217;s shared.</p><p>Find your team.<br>Reconnect.<br>Carry it together.</p><p>It matters more than you may know.</p><p></p>]]></content:encoded></item><item><title><![CDATA[Are You Listening to the Wind?]]></title><description><![CDATA[Heeding the Voices That Carry the Culture]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/listen-to-the-wind-not-just-the-weather</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/listen-to-the-wind-not-just-the-weather</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 18 Apr 2026 13:03:06 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/d97f1b16-afef-425e-a93b-5d17b38cf5e7_2000x1545.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>We&#8217;re back.</p><p>Spring break has come and gone, and I hope you are well-rested. And if you&#8217;re not: well&#8230;testing season has a way of finding us whether we&#8217;re ready or not. So go ahead and tighten your laces, take a deep breath, and prepare your mind.</p><p>But before the pace picks up, before the emails stack and the urgency returns:</p><p>Come on back. Sit with us for a moment on the milk crate.</p><p>There was a time when the old folks didn&#8217;t need dark clouds to tell them a storm was coming. They would step outside, pause, and say, <em>&#8220;You smell that? You feel that? Rain&#8217;s on the way.&#8221;</em></p><p>Clear skies above. Sun still rising. But something in the air had shifted.</p><p>They weren&#8217;t reacting to what they saw. They were discerning what they <em>felt</em>.</p><p>And in many ways, that&#8217;s the work before us now.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!2Zic!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F23ff7314-cc49-48db-a9ba-905051602be3_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!2Zic!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F23ff7314-cc49-48db-a9ba-905051602be3_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!2Zic!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F23ff7314-cc49-48db-a9ba-905051602be3_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!2Zic!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F23ff7314-cc49-48db-a9ba-905051602be3_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!2Zic!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F23ff7314-cc49-48db-a9ba-905051602be3_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!2Zic!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F23ff7314-cc49-48db-a9ba-905051602be3_1024x1024.jpeg" width="1024" height="1024" 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class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>A New Rhythm of Reflection</strong></h3><p>I want to take pause for a moment because we are excited to introduce a new devotional from <em>Lessons From The Milk Crate</em> titled <strong>Returning To The Milk Crate.</strong></p><p>Published every Sunday and Wednesday, these brief reflections are written for both teachers and school leaders who understand that education is more than a profession-it is our ministry.</p><p>Each devotional is rooted in faith and designed not only to encourage, but to empower educators to live out their faith through the work they do every day.</p><p>The inaugural devotional is now available, and we would be honored for you to read it and share it with someone who may need this reminder.</p><p>Read the first devotional here: <a href="https://bit.ly/47VI9TK">https://bit.ly/47VI9TK</a><br>And be sure to subscribe for free on Substack. </p><p>(There&#8217;s something about returning that steadies the soul.)</p><h3><strong>Disclaimer: What This Week Is </strong><em><strong>Not</strong></em></h3><p>Let&#8217;s be clear about something.</p><p>This week is not about reacting to everything. We already have enough fires to put out. But as my father used to say, <em>&#8220;You don&#8217;t respond to the ramblings of fools.&#8221;</em></p><p>Now, that doesn&#8217;t mean we dismiss people either. It doesn&#8217;t mean we ignore concerns or silence voices that need to be heard. But it does mean we must be discerning.</p><p>This is not about chasing every rumor. Not about untangling every piece of gossip. Not about exhausting ourselves trying to convince those who critique from the sidelines while refusing to carry weight in the work.</p><p>Because if we&#8217;re not careful, we will spend so much time reacting to noise that we stop listening to what actually moves the organization forward.</p><p>And here&#8217;s the tension:</p><p>The very people who <em>are</em> the wind in your organization-the high performers, the steady hands, the ones pulling the sails-they can grow weary too.</p><p>Weary of carrying more. Weary of overextension.</p><p>But just as likely: weary of watching energy poured into noise instead of progress.</p><p>And if the wind grows tired, the whole ship slows down.</p><p>And if we&#8217;re honest, there&#8217;s another layer to this:  My grandmother used to say, <em>&#8220;You can&#8217;t tell the doctor the medicine doesn&#8217;t work if you never take it.&#8221;</em></p><p>And sometimes, in our organizations, the loudest frustrations come from places where the prescribed supports-the structures, the systems, the expectations-haven&#8217;t been fully embraced, let alone consistently applied.</p><h3><strong>When Knowing Isn&#8217;t Doing</strong></h3><p>Have you ever encountered someone who seems to know everything but can&#8217;t quite <em>show</em> it?</p><p>I remember a relative bringing home a new partner once. She was kind, engaging, eager to connect. But she had one of those traits that made conversation&#8230;complicated.</p><p>She knew everything. And if she didn&#8217;t, her phone made sure she did within seconds.</p><p>Education. Politics. Finance. Religion. Healthcare. Sports. Personal development. You name it, she had a fact or opinion.</p><p>And yet, what quietly revealed itself over time was something else entirely.</p><p>Application was lacking.</p><p>(My grandmother had a way of saying things plain: <em>&#8220;I wouldn&#8217;t go to broke banker, a dying doctor or [an unhealthy] fitness trainer.&#8221;</em>)</p><p>There was a disconnect between what was said and what was lived.</p><p>Now, this isn&#8217;t about that individual. She was alright. She probably meant well.</p><p>But it <em>is</em> a reminder. We encounter this more and more-personally and professionally.</p><p>Voices that are loud with opinion but light on application or contribution.</p><p>And if we&#8217;re not careful, those voices can begin to shape our perception of reality more than the steady work happening all around us.</p><p>And if we bring that a little closer to home, we&#8217;ve seen this before.</p><p>The lessons that never quite planned ahead, but engagement is the concern.<br>The classroom where instruction takes a backseat to packets and worksheet, but rigor is the complaint. The expectations that aren&#8217;t reinforced-no calls home, no referrals, no requests for support, but behavior becomes the headline. The consistent absences or late arrivals&#8230;who feel the weight when asked to cover for others.</p><p>Not out of malice. Not always even out of neglect. But out of a disconnect between expectation and execution.</p><p>And over time, that disconnect can sound a lot like expertise even when it isn&#8217;t producing impact.</p><h3><strong>The Morning We Smelled the Rain</strong></h3><p>I remember a morning on the crate, waiting for buses to arrive. The sun was stretching over the horizon, sky clear, everything calm.</p><p>Then the wind shifted.</p><p>A mentor of mine paused and said, <em>&#8220;You smell that? I can hear the winds changing too. Rain is coming.&#8221;</em></p><p>I looked up. No clouds. No sign of a storm. But he wasn&#8217;t looking at the sky.</p><p>He was smelling the air and listening to the wind.</p><p>At the time, we were in a season of progress. Growth was evident. Systems improving. Culture strengthening.</p><p>And yet, there were pockets of negativity. (Reality check: there always will be.)</p><p>Voices insisting nothing was working. Concerns that, when unpacked, fell into different categories:</p><ul><li><p>Some valid and solvable</p></li><li><p>Many self-induced</p></li><li><p>Some isolated incidents that had grown through gossip into full organizational &#8220;failures&#8221;</p></li></ul><p>And if we told the whole truth, some of those concerns were rooted in something deeper-a reluctance to fully engage the very practices designed to support success. Because it&#8217;s difficult to measure the effectiveness of systems we haven&#8217;t consistently used.</p><p>And then my mentor said something that stayed with me:</p><p>&#8220;Every organization has problems. That&#8217;s your job security. But not every problem is a storm.&#8221;</p><p>Then he leaned in just a bit more, &#8220;Listen to your winds.&#8221;</p><p>Measure your progress with clarity. Heed the insight of those doing the work.</p><p>Yes, address concerns. Yes, solve what can be solved. Yes, have the hard conversations when needed. But don&#8217;t let the weakest links determine the forecast for the entire organization. Don&#8217;t let sideline commentary outweigh on-the-field performance.</p><p>Because sometimes it <em>looks</em> like a storm is coming&#8230;and it&#8217;s just overcast.</p><p>And other times, it&#8217;s raining while the sun is still shining. </p><p>Discernment matters.</p><h3><strong>A Return in the Middle of Leadership</strong></h3><p>Years later, I found myself sitting at a table, not a crate, but the lesson was the same.</p><p>As a principal, we had made real progress. Data supported it. Culture reflected it. Growth was undeniable. And yet, a handful of voices couldn&#8217;t see it.</p><p>Frustration had turned into misperception. Misperception into narrative. Narrative into urgency.</p><p>&#8220;What are we going to do?&#8221; my team asked.</p><p>Because two or three individuals were unhappy-and even considering leaving-the weight of their dissatisfaction began to distort our collective view.</p><p>So I asked a simple question:</p><p><em>&#8220;Are we listening to the wind&#8230;or are we making forecasts based on emotion?&#8221;</em></p><p>And in that moment, we realized we had allowed a few voices to shape our understanding more than the evidence and the experience of those carrying the work. We reset.</p><p>We listened carefully. We validated what needed validating. We offered support where it was needed. And we had honest conversations when the concerns pointed back to individual growth. Then we went to our wind - the hard workers, the lead teachers, the dedicated ones, and we checked their forecast.</p><p>We didn&#8217;t ignore the weather. But we followed the wind.</p><h3><strong>What This Means for Us</strong></h3><p>Now please know this clearly: this is not an invitation to dismiss critique.</p><p>It is not permission to lead with blinders on. It is not a call to create an &#8220;us vs. them&#8221; culture.</p><p>Healthy organizations <em>need</em> feedback. They require reflection. They grow through honest tension.</p><p>But wisdom is knowing the difference between feedback that builds and noise that distracts. Between concern that invites growth and criticism that avoids responsibility. </p><p>We must remain open but not easily shaken. Responsive but not reactive. Grounded enough to hear every voice, and discerning enough to know which voices are carrying the weight of the work.</p><p>There will be moments when we must say, with both clarity and care:</p><ul><li><p>We cannot allow inconsistent practice to dictate organizational reality.</p></li><li><p>We cannot treat unimplemented strategies as ineffective strategies.</p></li><li><p>And we cannot let frustration replace responsibility.</p></li></ul><p>Because when we do, we risk building narratives that feel true but aren&#8217;t rooted in the full picture.</p><p>All of this said, because leadership is not about ignoring the sky-it&#8217;s about correctly interpreting it.</p><h3><strong>The Heart of the Lesson</strong></h3><p>High performers don&#8217;t just produce results, they <em>carry direction</em>. They are the wind in your organization. But the wind is not found in intention alone-it&#8217;s revealed in their consistent, faithful execution.</p><p>And if we are going to lead well, we must:</p><ul><li><p>Listen closely</p></li><li><p>Discern wisely</p></li><li><p>Act faithfully</p></li></ul><p>Not every loud voice is a leading voice. Not every storm is a storm. And not every forecast deserves our full attention.</p><p>But the wind will always tell you where you&#8217;re really going and what&#8217;s coming.</p><h3><strong>Reflection for the Week</strong></h3><ol><li><p>Who are the &#8220;wind carriers&#8221; in our organization and how often do we intentionally listen to them?</p></li><li><p>Where might noise be distorting our perception of progress?</p></li><li><p>How are we balancing validation of concerns with accountability for growth?</p></li><li><p>Are we reacting to the sky or discerning the wind?</p></li></ol><h3><strong>A Continued Invitation</strong></h3><p>As we continue this journey, we invite you again to engage with our new devotional, <strong>Returning To The Milk Crate.</strong></p><p>These reflections are designed to ground us, challenge us, and remind us that this work is a sacred calling.</p><p>Take a moment this week to read, reflect, and share: <a href="https://bit.ly/47VI9TK">https://bit.ly/47VI9TK</a></p><p>Because sometimes the clarity we need in leadership is found in the quiet discipline of returning.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h3><strong>Recognition</strong></h3><p>This week, I am grateful for the steady ones.</p><p>The educators who show up early and stay late not for recognition, but for impact. The leaders who carry both vision and weight with quiet strength.<br>The colleagues who keep pulling the sails even when the winds feel uneven.</p><p>May we honor them-not just with words, but with our attention.</p><p>Listen to them.<br>Learn from them.<br>Lead with them.</p><p>Follow the wind.</p><p>It matters more than you know.</p>]]></content:encoded></item><item><title><![CDATA[Finishing Well]]></title><description><![CDATA[Using the Time We&#8217;re Given So We Can Truly Rest]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/finishing-well</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/finishing-well</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 04 Apr 2026 13:20:38 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/2d4d83ac-bfe0-4f5d-9a91-f5a70a8223a5_2000x1545.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I can still see that milk crate. Not polished. Not padded. Not something you&#8217;d ever put on display-but steady. Always steady. (And if you&#8217;re new here and wondering what the &#8220;milk crate&#8221; is, there&#8217;s a beginning to that story <a href="https://jtannercurry.substack.com/p/lessons-from-the-milk-crate">here</a>.)</p><p>It sat in places where conversations mattered more than appearances. Where wisdom didn&#8217;t rush. Where somebody-usually a step or two ahead of you-would lean back, take a breath, and say something that stayed with you longer than you expected.</p><p>The milk crate wasn&#8217;t about escape. It was about alignment.</p><p>It was where we remembered not just <em>why</em> we worked-but <em>how</em> to work in a way that could last.</p><p>Last week, we sat on that crate and talked about rest. About the truth that has followed many of us into late nights and early mornings: <a href="https://jtannercurry.substack.com/p/you-cant-pour-from-an-empty-cup">you cannot pour from an empty cup</a>.</p><p>This week, we stay seated-but we shift the conversation. Because rest doesn&#8217;t just happen. It must be prepared for.</p><p>And if we&#8217;re honest, many of us don&#8217;t struggle with the idea of rest. We struggle with <em>getting there well</em>.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!ZCwd!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!ZCwd!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!ZCwd!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!ZCwd!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!ZCwd!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!ZCwd!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://jtannercurry.substack.com/i/193161891?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!ZCwd!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!ZCwd!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!ZCwd!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!ZCwd!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F450d662e-561d-4b5d-83e6-52b464ed51a2_1024x1024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>Disclaimer: What This Is Not</strong></h3><p>Let me say this plainly-because clarity protects us. This is not about working until the work is done. Because the work will never be done.</p><p>There will always be another email. Another need. Another conversation waiting just beyond the one you just finished.</p><p>I once worked alongside a leader who gave everything-12 to 14 hours a day on campus, then more from home, then weekends that barely felt like weekends. Work had stopped being what she did. It had become who she was.</p><p>And if you watched closely, you could see it. The exhaustion. The edge. The quiet weight of always being &#8220;on.&#8221;</p><p>This isn&#8217;t that.</p><p>This also isn&#8217;t a call to disconnect so completely that we lose the relationships that make the work meaningful. We are not returning to an assembly-line version of leadership-clock in, clock out, keep your head down, and don&#8217;t engage.</p><p>We are relational leaders. Present leaders. Invested leaders. But rather:</p><p><strong>Presence without boundaries becomes depletion. And depletion cannot sustain purpose.</strong></p><p>So this week is not about doing less meaningful work. It&#8217;s about doing the work <em>within the time we&#8217;ve been given</em>-so that when it&#8217;s time to rest, we can actually be present enough to receive it.</p><h3><strong>A Lesson Learned Before the Crate</strong></h3><p>Before I ever sat on that milk crate, I learned this lesson in a much less reflective place&#8230;The teacher&#8217;s breakroom.</p><p>Now, if you&#8217;ve spent any time in education, you already know-that space can be many things. Community. Laughter. Support. Gossip (Yes, that too). (And occasionally a 90-minute coffee break disguised as collaboration.)</p><p>I found myself there often. Talking. Sitting. Lingering. And then, as the day ended, I found myself staying late.</p><p>Making copies. Planning lessons. Preparing for tomorrow-while wondering why tomorrow always felt so heavy before it even began. Until a mentor teacher-kind, steady, and just direct enough to be effective-pulled me aside.</p><p>No lecture. No embarrassment. Just an observation. And then she shared a phrase her husband often told his students:</p><p>&#8220;Do what you gotta do now so you can do what you wanna do later.&#8221;</p><p>Almost too simple. But it stayed. So I made a few adjustments. Nothing dramatic. Just intentional. Less drifting. More focus. Less delay. More decision.</p><p>And what I found surprised me-the work still got done. In fact, most days, it got done <em>better</em>. And I left earlier. Prepared. Clear. Ready for the next morning.</p><p>But more importantly, when I got home, I was actually <em>there</em>. With my family. In conversation. In rest. Not physically present and mentally elsewhere.</p><p>That was the beginning of understanding:</p><p><strong>Rest is not found at the end of chaos. It is created through intentional stewardship of the time we&#8217;re given.</strong></p><h3><strong>And Yet&#8230;The Lesson Returns</strong></h3><p>Now let me be honest. As a school leader, I still wrestle with this. Because leadership brings a different kind of demand.</p><p>Fires don&#8217;t schedule themselves. Needs don&#8217;t wait their turn. And just when you think you&#8217;ve cleared one thing, three more quietly step into its place. And if I&#8217;m not careful, I drift. Not in the breakroom anymore-but in responsibility.</p><p>Lingering too long in one place. Carrying things I should have delegated. Letting urgency dictate my pace instead of purpose. And recently, I saw the cost more clearly than I wanted to admit.</p><p>My mind was at work even when I wasn&#8217;t at work. In church-thinking through the coming week. At dinner-half-listening, half-planning. In sleep-dreaming about unfinished tasks then waking up to finish them at 2 a.m.</p><p>And here&#8217;s the tension that sat heavy: I was encouraging others to find balance but I wasn&#8217;t practicing it. (And people don&#8217;t learn from what we say nearly as much as they learn from what we live.)</p><p>So I had to do something simple-and difficult. I called time out. Not from the work. But from the <em>way</em> I was working.</p><p>I went back to the crate. Reflected on last week&#8217;s lesson. And then made a conscious decision:</p><p>Protect the time during the day. Handle what must be handled-<em>when it can be handled</em>. Be present where my feet are. And while it wasn&#8217;t perfect, something shifted.</p><p>For the first time in a while, I entered a break-not carrying everything with me. But laying some things down.</p><p>And there was peace there.</p><h3><strong>What This Means for Us</strong></h3><p>As we move toward Easter,  toward spring break,  toward a moment that invites rest, we have a choice.</p><p>We can stumble into rest exhausted, distracted, and still carrying everything we never set down or we can prepare for it.</p><p>By honoring the time we&#8217;ve been given now.</p><p>That means:</p><p>We work with intention-not just effort.<br>We prioritize-not just react.<br>We finish what we can-<em>when we can</em>.</p><p>Not because the work is ending but because <strong>we are creating space to be whole when we step away from it.</strong></p><p>Because rest isn&#8217;t just about stopping. It&#8217;s about <em>arriving</em>.</p><p>Fully present. Fully aware. Fully available to the people and moments that matter most.</p><h3><strong>The Heart of the Lesson</strong></h3><p>Let me say it plainly:</p><p><strong>Rest is not a reward for exhaustion. It is the result of intention.</strong></p><p>We don&#8217;t honor our calling by running ourselves into the ground.</p><p>We honor it by stewarding our time, our energy, and our focus in a way that allows us to keep showing up-whole.</p><p>So we do the work. We answer the call. We carry what&#8217;s ours to carry.</p><p>But we also remember:</p><p>&#8220;Do what you gotta do now so you can do what you wanna do later.&#8221;</p><p>And when that later comes-when the break arrives, when the holiday opens up we&#8217;re not just physically removed from work, we are <em>present in our rest</em>.</p><p>And that, in its own quiet way, is a form of leadership too.</p><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h3><strong>Reflection for the Week</strong></h3><p>As we move toward this season of rest, I&#8217;m holding these close:</p><ul><li><p>Where am I allowing time to slip away during the day that could be used with greater intention?</p></li><li><p>What is one adjustment I can make to better steward my work hours this week?</p></li><li><p>Am I finishing my days in a way that allows me to be present in my evenings?</p></li><li><p>Where has &#8220;being busy&#8221; replaced being purposeful?</p></li><li><p>What would it look like to enter this upcoming break with a clear mind and a settled spirit?</p></li></ul><h3><strong>Recognition</strong></h3><p>To the mentors who taught quiet lessons in passing moments-thank you for the wisdom that continues to return right on time.</p><p>To those early voices in classrooms and hallways who reminded me to use the time well-your words are still working.</p><p>To my colleagues and fellow leaders-walking this tension between responsibility and rest-we are learning together, even when we have to relearn.</p><p>And to my family-who receives what&#8217;s left at the end of the day-thank you for the grace to grow into giving you my best instead.</p><p>And somewhere, steady as ever that milk crate still sits. Reminding us that finishing well is not about doing everything. It&#8217;s about doing what matters-when we have the time to do it-so that when it&#8217;s time to rest we actually can.</p><p>So in the spirit of what we&#8217;ve just said-in the name of being fully present in our rest-we&#8217;re going to do something that doesn&#8217;t always come easy for us</p><p>We&#8217;re going to step away. No milk crate sit next week.</p><p>Not because the work isn&#8217;t there. Not because the lessons have stopped. But because we&#8217;re choosing to practice what we&#8217;ve just talked about-finishing well, setting things down, and actually entering into rest with intention.</p><p>So take the time. Be where your feet are. Laugh a little longer. Rest a little deeper. Be fully present in the moments that don&#8217;t come around often enough.</p><p>And then let&#8217;s come back together-clearer, fuller, and ready-for our next sit on April 18.</p><p>I&#8217;m already looking forward to it.</p><p>Take your rest.</p><p>It matters more than you know.</p>]]></content:encoded></item><item><title><![CDATA[You Can't Pour From An Empty Cup]]></title><description><![CDATA[The Work Requires Us...But So Does Our Well-Being]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/you-cant-pour-from-an-empty-cup</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/you-cant-pour-from-an-empty-cup</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 28 Mar 2026 13:02:55 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/9febb7bb-7307-44b0-99d6-342706feba9e_2000x1545.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I can still see my old <a href="https://jtannercurry.substack.com/p/lessons-from-the-milk-crate">milk crate</a>. Not polished. Not padded. Not impressive by any formal measure. But steady. Reliable. Always there. (And if you&#8217;re new here and wondering what the &#8220;milk crate&#8221; is, there&#8217;s a beginning to that story <a href="https://jtannercurry.substack.com/p/lessons-from-the-milk-crate">here</a>.)</p><p>It was where conversations slowed down just enough for truth to catch up. Where laughter and hard lessons shared the same space. Where somebody older, wiser, or simply more seasoned would lean back, take a breath, and remind you of something you didn&#8217;t know you were forgetting.</p><p>The milk crate was never about comfort. It was about clarity.</p><p>And every now and then, we come back to it-not because we&#8217;re tired of the work, but because we need to remember how to do the work well.</p><p>Last week, we talked about <a href="https://jtannercurry.substack.com/p/returning-to-the-crate">returning to the crate</a>. This week, we&#8217;re sitting on it a little longer to talk about taking care of ourselves while we lead.</p><p>Because as true as it sounds-<em>you can&#8217;t pour from an empty cup</em>-it&#8217;s even more true in the work we&#8217;ve been called to do.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!tNMF!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!tNMF!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!tNMF!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!tNMF!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!tNMF!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!tNMF!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/be644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://jtannercurry.substack.com/i/192398467?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!tNMF!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!tNMF!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!tNMF!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!tNMF!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbe644add-05d8-4f7a-a8f1-4c46629b72b6_1024x1024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong>Disclaimer: What This Week Is Not</strong></h2><p>Let&#8217;s be clear-because clarity matters.</p><p>This is <strong>not</strong> about working from 8 to 4, packing up, and leaving things undone that matter deeply to children, families, and staff.</p><p>This is <strong>not</strong> about building so many walls around your time that you become unreachable to the very people you&#8217;ve been called to lead.</p><p>I once met a leader-proud and confident-who told me none of his staff had his phone number, and that he left immediately after dismissal every single day.</p><p>I remember nodding politely. But inwardly wondering&#8230; <em>how&#8217;s that working for you? </em>I don&#8217;t think it did. Because leadership-real leadership-requires presence. It requires availability. It requires sacrifice.</p><p>So no, this is not about stepping away from the work. This is about sustaining yourself <strong>in</strong> the work.</p><p>Doing what&#8217;s necessary. Carrying what&#8217;s heavy. Showing up fully.</p><p>But doing it in a way that allows you to still be whole when you get there.</p><h2><strong>A Lesson from the Backyard</strong></h2><p>A few weeks ago-three days before my son&#8217;s first baseball game of the season-he jumped off the swingset and sprained his arm. Two weeks. Wrapped in a sling.</p><p>First two weeks of the season-gone. And then, just a few days later, I came home and saw him outside.</p><p>Sling off. Glove on. Standing in front of the pitch-back, throwing and catching like nothing had happened. Now, as any good parent would do, I stepped in quickly-reminding him that his arm needed rest.</p><p>And without hesitation, he looked at me and said, &#8220;Dad,, my team is counting on me.&#8221; (I&#8217;ll admit-something about that kind of natural commitment warms your heart&#8230;even after a $150 co-pay at the doctor&#8217;s office.)</p><p>But beneath that moment-beneath the pride, beneath the smile-there was something else: A mirror.</p><p>Because I had to ask myself: <em>How many times has he seen me do the same thing?</em></p><p>Working when I was too sick to work. Skipping appointments I knew I needed. Choosing the job-again and again-at the expense of my own well-being.</p><p>He wasn&#8217;t just playing through pain. He was modeling what he had seen.</p><h2><strong>A Hard Word from the Crate</strong></h2><p>Years ago, when I was running dangerously close to burnout, a mentor-one of those milk crate voices you don&#8217;t forget-looked at me and said:</p><p>&#8220;You could die standing up teaching and they wouldn&#8217;t hang the flag at half-staff.&#8221;</p><p>Now let me pause here-because that statement needs context.</p><p>This is <strong>not</strong> about diminishing the value of what we do. It is <strong>not</strong> about saying we don&#8217;t matter.</p><p>We matter deeply. We change lives. We shape futures.  We stand in moments that ripple far beyond what we can see.</p><p>But the truth she was pressing into me was this:</p><p>The work will continue. The building will open. The bell will ring.</p><p>And if we are not careful-if we neglect our health, our balance, our humanity-we may find ourselves unable to keep showing up for the very people we care so deeply about.</p><p>It wasn&#8217;t a statement about our insignificance. It was a warning about our sustainability.</p><h2><strong>When the Work Becomes Your Identity</strong></h2><p>Years later, sitting in the principal&#8217;s chair, I found myself living that warning out in real time.</p><p>Up at 3 or 4 in the morning-already working at the desk at home. Driving my kids to school-on the phone with a colleague. Working all day-without stopping to eat, without remembering to drink anything other than coffee. Leaving after 10&#8211;12 hours-still on calls, still answering, still carrying.</p><p>Then home.</p><p>Dinner. Bedtime routines. And right back to the laptop. Right back to the phone.</p><p>Because in that season, it didn&#8217;t feel excessive. It felt expected.</p><p>It felt like what the job required. Like what it took to <em>keep</em> the job.</p><p>But somewhere in the middle of all that motion, a question found me:</p><p><em>Had I stretched myself so thin that I could no longer fully serve the people I was called to lead?</em></p><p>And even harder:</p><p><em>Had I stepped so fully into leading my school that I had quietly stepped away from leading my family?</em></p><p>And if I was honest-<em>really honest</em>-</p><p><em>Had I neglected my own health- not out of necessity, but out of habit? Maybe even addiction to the work itself?</em></p><p>That milk crate voice came back again. Quiet, but clear. But this time, it didn&#8217;t rise from memory alone.</p><p>It came through the steady, seasoned wisdom of a mentor-my media specialist-whose career journey had already stretched across classrooms, principalships, district office administrations, and the long, quiet miles in between. She had seen what I was now learning to name. She had carried what I was just beginning to feel.</p><p>And with a grace that didn&#8217;t accuse and a clarity that didn&#8217;t waver, she reached back and handed me a lesson I thought I had already learned on that milk crate, but had somehow left behind.</p><p>She simply said:</p><div class="pullquote"><p>&#8220;You can&#8217;t pour from an empty cup.&#8221;</p></div><p>No spotlight. No sermon. Just truth.</p><p>And in that moment, the milk crate wasn&#8217;t just a place I remembered. </p><p>It was a place she helped me return to.</p><h2><strong>What This Means for Us</strong></h2><p>We are called to do important work. Work that demands time, energy, presence, and heart.</p><p>And because it matters so much, it can easily take everything.</p><p>But good leadership is not measured by how much of yourself you can deplete. It is measured by how well you can <strong>sustain</strong> your ability to serve.</p><p>That means:</p><p>We eat. We rest. We go to the doctor. We step away-when needed-not to abandon the work, but to return to it stronger.</p><p>We answer calls. But we also know when to put the phone down.</p><p>We give our best. But we don&#8217;t give what we don&#8217;t have.</p><p>Because an empty cup doesn&#8217;t just affect us-it affects everyone depending on what we pour.</p><h2><strong>The Heart of the Lesson</strong></h2><p>Here it is-plain and steady:</p><p>We cannot lead others well if we are quietly running ourselves into the ground.</p><p>We cannot model balance if we never practice it.</p><p>We cannot teach sustainability if we live in constant depletion.</p><p>And maybe most importantly-the people watching us closest  are learning how to live by watching how we lead.</p><p>So we do the work. We carry the responsibility. We show up fully. But we also take care of the vessel that&#8217;s doing the carrying.</p><p>Because leadership is not just about showing up today.</p><p>It&#8217;s about being able to show up tomorrow. And the next day. And the next season.</p><p>Still whole. Still present. Still able to pour.</p><h2><strong>Reflection for the Week</strong></h2><p>This week I&#8217;m holding a few questions nearer to my heart:</p><ul><li><p>Where in my life have I normalized unhealthy patterns in the name of dedication?</p></li><li><p>What is one practical way I can take better care of my health this week?</p></li><li><p>Am I modeling sustainability for those who are watching me closely?</p></li><li><p>Where do I need to create space-not to escape the work, but to strengthen my ability to do it well?</p></li><li><p>What would it look like to lead with both excellence <em>and</em> balance?</p></li></ul><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h2><strong>Recognition</strong></h2><p>To the mentors who spoke hard truths when I needed them most-thank you for loving me enough to challenge my pace.</p><p>To my family-who has patiently shared me with this work while reminding me who I am beyond it-thank you for your grace.</p><p>And to the leaders doing this work every day-showing up, carrying weight, making a difference-may we remember that taking care of ourselves is not stepping away from the mission&#8230;it&#8217;s ensuring we can keep fulfilling it.</p><p>And somewhere, not too far from here, that milk crate still sits waiting for us to pause, to listen, and to remember what really matters.</p><p>This week, let&#8217;s remember that we don&#8217;t honor the work by burning out for it. We honor the work by being well enough to keep doing it.</p><p>So this week, let&#8217;s do both.</p><p>Let&#8217;s show up. Let&#8217;s give our best. Let&#8217;s answer the call.</p><p>But let&#8217;s also take care of the one doing the calling back.</p><p>Take care of yourself. It matters more than you may know.</p>]]></content:encoded></item><item><title><![CDATA[Returning To The Crate]]></title><description><![CDATA[Leading Forward, Reaching Back]]></description><link>https://lessonsfromthemilkcrate.substack.com/p/returning-to-the-crate</link><guid isPermaLink="false">https://lessonsfromthemilkcrate.substack.com/p/returning-to-the-crate</guid><dc:creator><![CDATA[Lessons From The Milk Crate]]></dc:creator><pubDate>Sat, 21 Mar 2026 13:00:29 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/21d551f5-10f1-4510-b341-8f6a6e710360_2000x1545.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Before we go any further this morning, let&#8217;s remind ourselves what the milk crate is.</p><p>It&#8217;s not the crate itself. Never was.</p><p>It&#8217;s the space it created.<br>A space where wisdom sat low enough to be shared.<br>Where laughter softened hard lessons.<br>Where someone a few steps ahead of us paused long enough to say, &#8220;Let me tell you what I&#8217;ve learned.&#8221;</p><p>The milk crate was never about hierarchy. It was about proximity. About presence. About people.</p><p>And this week, this sit is a little different.</p><p>This is not a lesson built from something new I&#8217;ve learned.<br>This is a reminder-quiet, steady, necessary-that sometimes leadership requires us to return to the crate.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!DvP7!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!DvP7!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!DvP7!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!DvP7!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!DvP7!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!DvP7!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg" width="1024" height="1024" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1024,&quot;width&quot;:1024,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:172338,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://jtannercurry.substack.com/i/191667562?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!DvP7!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!DvP7!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!DvP7!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!DvP7!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1bc517cd-70e7-481d-8050-4b4632439bcc_1024x1024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg aria-hidden="true" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>A Necessary Disclaimer &#8211; What This Week Is Not</strong></h3><p>Let me be clear about what this week is not.</p><p>This is not about becoming overly dependent on the veterans of our craft.<br>Not about hiding behind their experience.<br>Not about asking them to carry what we&#8217;ve been called to lead.</p><p>Because at some point-sooner than we think-we are no longer the ones being developed. We are the ones responsible for development.</p><p>As teachers. As leaders. As stewards of the work.</p><p>We&#8217;ve all seen it.<br>Moments when the room grows quiet and eyes drift toward the veteran in the corner&#8230; waiting for them to fill the gap, to steady the moment, to carry the weight.</p><p>But leadership calls us forward.</p><p>Not to stand behind them. But to stand beside them.<br>And eventually to stand in their place.</p><p>This week isn&#8217;t about relinquishing that responsibility.</p><p>It&#8217;s about recognizing that even as we grow into leadership, we never outgrow the need for the crate.</p><h3><strong>Family &amp; Memory</strong></h3><p>Last week, my family gathered for a reunion.</p><p>Branches from each of my second great-grandparents&#8217; six children were represented. A room full of faces-some familiar, some distant, some that felt like reflections of people I once knew.</p><p>Family reunions like that&#8230; they&#8217;re interesting.</p><p>In one sense, it&#8217;s a room full of strangers sharing a meal. In another, it&#8217;s something deeper. Something sacred.</p><p>Because even when names escape us, connection doesn&#8217;t.</p><p>There&#8217;s a shared love. A shared lineage. A shared remembering.</p><p>And during our reunion, we held a memorial service.</p><p>One member from each branch came forward to light a candle in honor of those we&#8217;ve lost. A few words. A moment. A memory.</p><p>Then one of my cousins stepped forward.</p><p>A grown man. Seasoned by life. Strong in every visible way.</p><p>But in that moment, as he lit the candle, emotion found him before words did.</p><p>And all he could say was: &#8220;I miss my mom.&#8221;</p><p>That was it.</p><p>No long speech. No polished reflection. Just truth.</p><p>And in that moment, the room shifted.</p><p>For those of us still blessed to have our parents, it was a reminder. Of what we have. Of what we will one day lose. Of how deeply we are shaped by those who came before us.</p><p>And how, no matter how old we get, we never fully outgrow the need for them.</p><h3><strong>The Lesson About the Crate Itself</strong></h3><p>This week, I didn&#8217;t learn a new lesson from the milk crate.</p><p>Instead, I was reminded of the crate itself.</p><p>There was a time when my days were filled with those sits. Regular conversations. Easy access. Frequent laughter. Constant learning.</p><p>Then life moved.</p><p>Assignments changed. Roles shifted. Paths diverged.</p><p>And those daily milk crate moments became memories instead of routines.</p><p>At first, I thought the lesson was over.</p><p>But what I&#8217;ve come to understand is this:</p><p>The milk crate was never confined to a moment. It was forming something that could travel with me.</p><p>The value wasn&#8217;t just in sitting there then&#8230; It was in what those moments deposited in me for now.</p><p>And every now and then, life invites-or requires-us to return.</p><h3><strong>When the Calls Come Back</strong></h3><p>This past week held a little bit of everything.</p><p>Strain. Stress. Big decisions. Weariness. And, strangely enough&#8230; excitement. (Isn&#8217;t it something how leadership can hold all of that at the same time?)</p><p>And in the middle of that kind of week, something unexpected happened.</p><p>One by one, I found myself on the phone with four of my old milk crate mentors.</p><p>No planning. No formal agenda. Just connection.</p><p>We laughed. We reminisced. We talked through life and leadership.</p><p>But more than anything I listened, and by the end of the week, I realized something I hadn&#8217;t fully named before:</p><p>Those calls steadied me.</p><p>Not because I needed someone to solve my problems. Not because I was looking to hand anything off.</p><p>But because there is a kind of wisdom and a kind of peace that only comes from sitting with those who helped shape you.</p><p>It took me back to that moment with a distant cousin.</p><p><em>&#8220;I miss my mom.&#8221;</em></p><p>Different context. Same truth.</p><p>No matter how far we go there is something sacred about going back home.</p><h3><strong>What This Means for Us</strong></h3><p>So what does this mean for us-as leaders, as educators, as people still becoming?</p><p>It means we hold two responsibilities at the same time.</p><p>We step <em>forward</em> into leadership. And we stay connected to those who helped form it.</p><p>We grow into being the steady voice in the room. And we remain humble enough to still seek steady voices when needed.</p><p>We do not lean in a way that weakens us. But we do return in a way that strengthens us.</p><p>Because returning is not regression.</p><p>Returning is renewal.</p><h3><strong>The Heart of the Lesson</strong></h3><p>Here it is-plain and simple:</p><p>We can be called to lead and still need to sit.</p><p>We can carry responsibility and still need to listen.</p><p>We can become the veteran and still need the voices that helped shape your beginning.</p><p>And every now and then-when the weight feels heavy, when the road feels long, when the decisions feel layered&#8230;</p><p>We don&#8217;t need a conference. We don&#8217;t need a program. We don&#8217;t need a solution.</p><p>Sometimes we just need the crate.</p><p>A conversation. A voice. A moment that reminds you who we are and where you&#8217;ve come from.</p><p>Because the same wisdom that formed us then still has a way of sustaining us now.</p><h3><strong>Reflection for the Week</strong></h3><p>This week, I&#8217;m holding a few questions close to my heart:</p><ol><li><p>When was the last time I intentionally &#8220;returned to the crate&#8221; with someone who helped shape me?</p></li><li><p>Am I balancing my responsibility to lead with my need to remain connected and grounded?</p></li><li><p>Who are the voices I can call-not out of dependence, but out of wisdom and relationship?</p></li><li><p>In what ways am I becoming the kind of leader others will one day need to return to?</p></li><li><p>What would it look like to create space this week for one meaningful, unhurried conversation?</p></li></ol><p class="button-wrapper" data-attrs="{&quot;url&quot;:&quot;https://lessonsfromthemilkcrate.substack.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe now&quot;,&quot;action&quot;:null,&quot;class&quot;:null}" data-component-name="ButtonCreateButton"><a class="button primary" href="https://lessonsfromthemilkcrate.substack.com/subscribe?"><span>Subscribe now</span></a></p><h3><strong>Recognition</strong></h3><p>This week, I&#8217;m grateful for the voices that have walked with me-past and present.</p><p>For mentors who never required me to stay small, but always made room for me to grow.</p><p>For family-both by blood and by bond-who remind me where I come from and why it matters.</p><p>And for those unexpected moments-those unplanned calls and those quiet returns to the crate that come right when we need them most.</p><p>The milk crate may not always sit where it once did. But its presence, its impact, its invitation-that stays with me.</p><p>And every now and then, we find our way back.</p><p><strong>So this week, don&#8217;t just carry the weight-make the call.</strong></p><p><strong>Return to the crate. Not because you have to&#8230; but because you can.</strong></p><p><strong>Sit for a moment. Listen a little longer. Honor the voices that helped shape yours.</strong></p><p><strong>And then rise.</strong></p><p><strong>Rise with clarity. Rise with steadiness. Rise ready to be for someone else what they have been for you.</strong></p><p><strong>Keep working.<br>Keep growing.<br>Keep returning when you need to.</strong></p><p><strong>Because the crate still matters more than we sometimes realize.</strong></p>]]></content:encoded></item></channel></rss>