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Nedra and I went to the casino on a Friday night. We wanted something different for date night, and she had the idea. Dinner first, then we split a hundred dollars between us, fifty each. She headed for the nickel slots, her old favorite from a Vegas trip years back. I found the craps table.

I barely know how to play craps. My uncle taught me the basics years ago, and his rules usually work for me. That night they didn’t. I put my first twenty down and won it. So I did what every greedy gambler does. I bet bigger. I lost every hand after that.

I was down to my last chip when Nedra walked up behind me. She looked at the two men standing on either side of me, each with three or four thousand dollars in chips stacked neat in their trays. Then she looked at my one chip. It was a look of pity. I told her, “yeah, I feel a little insecure.”

The man next to me must have heard it. He didn’t say a word. He just dropped two twenty-five dollar chips on the table in front of me and went back to his game.

“Thanks, man,” I said. He nodded and kept playing.

Those two chips mattered, and afterward I began to win. I continued to play for awhile and walked away with nearly all our hundred dollars back. Yeah I know, frivolous, privileged, but still, I can’t stop thinking about why he just dropped me those chips. Why did he do that? Pity? Some superstition that I was good luck? I don’t know. But I guess I sort of see it (i’m a generally optimistic person) as just a little help.

The next day, I began to think about people in my life that “dropped chips” in front of me when I needed a little help. I simply didn’t get where I am by myself, and neither did you. Somebody dropped chips in front of you too.

We tell ourselves a different story in leadership. Everybody playing their own hand at their own table. You built your stack, you take credit for the wins, you own the losses, and you don’t expect anybody to bail you out. It’s a good story if you want to feel self-made. It’s mostly a lie.

Every leader I know doing work that matters, in a school district, a nonprofit, a foundation, can point to a moment when somebody dropped chips in front of them for no earned reason. A board chair who vouched for them before they had a track record. A colleague who quietly covered a mistake. A funder who wrote a check on relationship instead of a five-year plan. At least I know these are true for me.

We rarely say that part out loud. In philanthropy and nonprofit work especially, everything gets measured, benchmarked, justified. Merit is the language everyone speaks. But look closely at your own path and you’ll find the chips other people dropped in front of you when you had one measly stack and a look of insecurity on your face.

That’s the real difference between transactional leadership and transformative leadership. Transactional leadership asks what you earned. Transformative leadership looks at what you need and hands it over before you’ve proven anything. One runs on merit. The other runs on relationship. Every organization I’ve ever worked inside needed more of the second and had far too much of the first.

Change doesn’t happen because somebody built a better system for tracking who deserves what. Change happens when somebody at the table, with more than they need, decides to drop some of it in front of somebody who has less. Nobody wrote that into a policy. Nobody put it on a slide. The man next to me at the craps table didn’t consult a strategic plan before he moved his chips.

Here’s the practice. Do it today, not someday.

Name one person, out loud or in writing, who dropped chips in front of you before you’d earned it. Be specific. Not “my mentor.” The actual person, the actual moment. Then tell them. A text is enough. “I don’t think I ever told you what that meant.”

Then look around your table right now. Somebody on your staff, in your cohort, at your kitchen table, is down to one measly chip and working hard to look like it doesn’t bother them. You already know who it is.

Drop something in front of them this week. An honest compliment, a word of encouragement and solidarity, vouch for them in a room they’re not in. Cover a mistake without mentioning it later. Write the check before the outcomes are guaranteed.

Casinos are built so the house always wins. Every rule, every payout, every flashing light is designed to take more than it gives. And still, somewhere in the middle of all someone can choose to rig the odds in your favor for no reason at all. Rig them for somebody else this week. I will never know that guys name, but I remember what he did. We can all be the guy with the chips and drop a few for someone who needs them.

He was right. And I have heard some version of this for years.

There is a real gap between what inspires people in the room and what actually happens when they get back to the office. Budget cuts. Resistant supervisors. Teams that don’t have the language yet. Cultures that are not ready. I recognize those constraints are real. The bureaucracy, the history, the systems and structures that get in the way of the kinds of changes I am talking about are real.

Here is what I want to say about that: inspiration without infrastructure is just a feeling. Being moved by an idea is not enough. Something has to happen with it.

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I have sat in a lot of rooms with the people who do some of the hardest work in this country. Public school districts. Government agencies. Nonprofits. The organizations built to serve our communities, staffed by people who show up in the space between institutions and the people they’re supposed to help, holding the two together with trust, presence, and sheer force of human will.

And in almost every one of those rooms, sooner or later, someone says what many of us are thinking.

It’s us versus them here. Nobody is really being a team.

The room goes still, quiet with recognition rather than surprise. Everyone already knows it’s true.

The Many Faces of Us vs. Them

It rarely shows up the same way twice. But you know it when you see it.

Lived experience versus those without it. The people who came up out of the community deciding the ones who didn’t could never really understand, and the ones with the credentials quietly deciding the ones with the stories aren’t rigorous enough to lead.

Leadership versus frontline staff. The ones making the decisions and the ones absorbing them, each convinced the other has no idea what the day actually requires.

Academic achievements versus lived wisdom. Whose knowledge counts. Whose gets called anecdotal.

The ones who are “about the work” versus the ones treated as if they never were. A purity test dressed up as commitment.

Profit versus purpose. Program versus people. Staff versus the very families they were hired to serve.

The list goes on, and every one of these divisions shares something. Each takes an organization built around a shared why and splits it quietly into sides, moving the group further from mission and closer to fight. The people caught inside it usually miss what’s happening, because their certainty that they’re the ones who truly care or understand is exactly what blocks the view.

The Architecture of Opposition

Us versus them lives deeper than personality or communication. It runs deeper than any team-building retreat or fresh strategic plan could reach.

It’s what happens when an institution consistently makes decisions about people without including those people in the process.

I heard it named once, and the precision of it has stayed with me. We’re told constantly to build decisions with the community, with staff, as a shared process. Yet leadership skips that step at the top. People get told what they need instead of asked. Hey, we want you to do this. Hey, we’re changing things up.

That read less like complaint and more like diagnosis. The institution preaches inclusion while practicing imposition, and the people on the receiving end of that contradiction understand exactly what’s happening to them. They’re just exhausted from navigating it.

I can see why people are resistant to change, someone told me. They’ve been done dirty too many times.

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The Wound Underneath the Wall

Us versus them starts with hurt, long before it turns into hostility.

It starts when a community member brings a concern and feels dismissed. When a frontline worker raises an issue and gets managed instead of heard. When a staff member offers an idea and watches it disappear into a process that was never really built to receive it. When people who were promised things they never received stop believing the promise means anything.

Each moment is small and, alone, survivable. But they accumulate into something heavier than frustration: a hardened conviction that the institution serves everyone but me, that the people running it stand somewhere else. Self-protection starts to look like the only rational response.

That conviction is rational. It’s learned, and unlearning it takes far longer than acquiring it did.

The Irony Everyone Sees and Nobody Names

A particular kind of damage happens when an organization’s stated values are visibly out of step with its actual practices.

It’s attentiveness rather than naivety.

When an organization tells its staff to meet people where they are, to listen before acting, to build trust through genuine relationship, and then those same staff get managed the opposite way, told rather than asked, evaluated rather than supported, blamed rather than developed, something corrosive happens.

People stop believing the values are real and start reading them as performance instead. That reading spreads fast, driven by attention rather than cynicism. What people watch and what they’re told stop lining up.

Us versus them thrives in that gap. It feeds on the distance between what an institution says it believes and what the people inside it actually live.

Asking people to practice trust downward while they live distrust upward asks too much. People teach what they know, and what they know is what they’ve lived.

What Sits Underneath the Opposition

After a long time in this work, I’ve landed on this: most people on every side of every us versus them divide are afraid of each other, or exhausted by each other, more than actually opposed. Some tried once to reach across the divide, felt the reach go unreturned, and decided the cost of trying again ran too high.

The community member who shows up hot usually isn’t hostile by nature. She’s learned that softness gets ignored and volume is the only language this place responds to.

The frontline worker who keeps their head down and stays in their lane isn’t indifferent. They’ve learned that going above and beyond earns no recognition, sometimes earns resentment, and that self-protection is the safer bet.

The leader who communicates by memo instead of conversation still cares. They’ve learned that vulnerability in leadership reads as weakness, and that the institution rewards control over connection.

None of these people started here. They arrived here, through a long sequence of small experiences that taught them this was the safest way to survive in this particular place.

It’s a culture problem wearing a character costume. Culture problems get fixed by changing the conditions that produce the behavior, never by targeting individuals.

The Move From Opposition to Proximity

So what’s the antidote?

It’s proximity. Sustained, uncomfortable, non-transactional proximity.

It’s leaders who ask rather than tell. Who stay in the room after the presentation ends and listen to what people say once the agenda is done. Who make decisions at the pace of trust instead of the pace of the calendar.

It’s institutions that treat the people closest to the pain as the people closest to the solution: human beings holding information no leadership team can reach unless it builds the conditions for that information to be shared.

Buy-in evaporates the moment people feel unheard by their leaders, the moment leadership talks a walk it never takes.

That’s the whole thing. Buy-in is earned in daily, unremarkable, essential practice, treating people like their experience of this institution actually matters. No communication strategy or slide deck substitutes for that.

It either happens or it doesn’t. The people inside the building already know which one is true.

The Mirror We Keep Avoiding

This next part is the hardest, so brace yourself.

It’s easy to read everything above as a description of them: the leaders who never listen, the agency that imposes, the system that wounds. Stop there, and you’ve just done the exact thing this piece warns against. Lens aimed outward, landing once again on someone else as the problem.

The first of the Four Pivots moves from lens to mirror, from analyzing everyone else to examining yourself. Us versus them is the hardest place to make that turn. Our certainty that we’re the ones who truly care is exactly what convinces us we stand outside the divide.

But we are. All of us. I am.

I remember earlier in my career, I redesigned our entire org chart alone. Reporting lines were tangled, teams overlapped, and work kept slipping through cracks nobody could name, so I sat down one weekend, mapped the whole organization from memory and instinct, and rolled it out Monday morning like a finished gift. My team opened it and felt the ground shift under decisions they’d never touched. I’d solved a structural problem and created a trust problem in the same motion, and I couldn’t see it happening because I was so sure the chart itself was the fix. Being right about the structure gave me zero permission to be closed toward the people who had to live inside it.

So before you close this, resist pointing these questions at someone else in the room. Turn them toward the mirror instead.

Where does us versus them live in your organization right now? Skip the abstraction. Name the groups, the decisions, the wounds that went unacknowledged and unrepaired.

And the harder one. What has your leadership, your pace, your priorities, your certainty, done to produce or sustain that divide?

When you feel most sure you’re right, what gets harder for you to see?

Who have you quietly sorted onto the other side, so you wouldn’t have to sit with the discomfort of understanding them?

This is an invitation, the same one I keep having to accept myself.

Us versus them is a symptom, never the natural state of human communities. It’s what happens when something goes unaddressed long enough to calcify into culture.

And culture, however hard it is to change, was made by people. Which means it can be changed by people.

Starting with the ones honest enough to look in the mirror, including the one who built an org chart alone, and refuse to look away.

First, a school district where community liaisons have built something rare: a team that goes door to door asking families not what they need but what they dream about.

Second, Chicago …

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I almost missed it.

We were wrapping up. The facilitator had just announced we had five minutes left, and I could feel the room beginning to shift toward the logistics of what came next. Someone named Ron raised his hand.

“I think for me it’s just having that group, having that family. Kind of what we do like when we have our Pink Tuesdays.”

I stopped him. “What are Pink Tuesdays?”

What he told me next is the reason I am writing this piece.

I spent a full day recently inside a California school district that has been living with something most districts are too afraid to name directly: a long, layered history of racial tension between its Black, Brown, and White communities. A wound that goes back not years but generations. The kind of tension that doesn’t live in policy documents. The kind that accumulates in hallways and parent meetings and unspoken rules about whose pain gets acknowledged and whose gets managed.

I was there from morning to late afternoon. I met with the superintendent and district leadership. I sat with the frontline staff doing the work of building relationships between the school and families who have every reason not to trust institutions. I ended the day inside an elementary school, hearing firsthand what transformation looks like when one leader decides to stop waiting for permission and starts building.

They were a tight knit group who all knew their mission was to be out in the neighborhood, working with students, care givers and families. Listening to them sounded like a team, or crew that had been through tough stuff and survived to tell about it.

But the moment that has stayed with me happened in the morning. In a room full of community school liaisons. And it was about Pink Tuesdays.

Who These People Are

Community school liaisons occupy a particular kind of liminal space. They are not quite teachers. Not quite administrators. The families they serve don’t see them as the “school” and that, it turns out, is exactly why they are trusted.

“They see us a part of the community, not really representing the school”

That is not a program... its a type of trust that takes years to develop, cultivate and protect.

They described doing “warm transfers” when children transition from elementary to middle school. Rather than simply passing a folder, they make a personal phone call to a trusted colleague at the receiving school: “I got this kid coming over. When they get there, go see him. He’s just like me and he’ll be there for you too.” The relationship travels with the child.

And then Ron said the thing about Pink Tuesdays.

Pink Tuesdays

Once a month, the liaisons gather in subgroups. No administrators. No formal agenda. Just them.

The name came from something mundane. Their professional development calendar for the school that highlights certain Tuesdays in pink. Someone started calling them Pink Tuesdays. It stuck.

But what happens inside them is anything but mundane.

“We come to connect as people, not employees”. Ron explained. “We talk about everything from how we’re dealing with our job, personal things, plus how can we improve ourselves.”

Another person jumped in. “We realized we needed time to sit down and build real relationships, support each other with what we see out there and what we’re going through. It’s not just about the job. It’s about the whole person.”

When I asked Ron what he needed more of, he came back to Pink Tuesdays without hesitation. “Just having that support with your team. Where I can make a text message, I can make a phone call, and I know I’ll get some answers from somebody.”

He told a story about an ankle injury. He had found a cream that helped before his surgery. Nothing work-related. He mentioned it to a colleague in one of those Tuesday gatherings. She tried it. It worked. He laughed telling it. “Things like that are what keeps our group strong. Because we see the value in each other.”

I sat with that for a moment. An ankle cream. A small, ordinary human thing shared between colleagues who had built enough trust to share ordinary human things. And in the same breath, the same relationship, these people navigate the most difficult family crises in the district, hold space for communities shaped by decades of mistrust, and go home and carry it alone until the next Pink Tuesday.

What Pink Tuesdays are really doing

Nobody assigned Pink Tuesdays. Nobody created them as a professional development initiative or a wellness program or a retention strategy. They emerged because the people doing this work recognized something that no organizational chart acknowledged: you cannot pour from an empty vessel, and this work empties you.

They created their own container for replenishment. Monthly. Voluntary. In a room without their supervisors. Talking about the personal and the professional in the same breath because they understand that those two things are not separate, no matter how much the institution pretends they are.

This is what healing centered engagement looks like from the inside. Not as a training you attend or a certificate you earn. As a practice you build into your own life because you understand, bone deep, that the work of holding other people’s humanity requires you to be held too.

Underneath the beauty, this soul work, this community had to build this space for themselves. Because nobody built it for them.

One person put it plainly. “We’re like a car that keeps on running, but nobody’s putting oil in it.” The district runs programs. It trains staff. It moves through the calendar. But the people doing the hardest relational labor in the building — the ones who are called when the parent won’t calm down, the ones who comfort children, the ones who know what it feels like to be rejected. Those people have had to oil themselves.

Pink Tuesdays are self-administered oil.

That is the whole thing. That is the entire framework I have spent my career trying to articulate

Human beings do their best work when they feel like human beings.

This should not be a revelation. It should be the foundation of every institutional policy, every budget decision, every leadership conversation.

And it is not. Not yet. Not in most places.

What This Is The Beginning Of

I want to be clear about something: what I witnessed in this district is not a finished thing. It is a beginning. The forces that produce distrust in school communities have been accumulating for decades. The good people at every level who work at this district inherited these issues, they didn’t create them. They will not be undone in a grant cycle or a professional development sequence or even a very good keynote.

What makes me hopeful is not the programs. It is Pink Tuesdays.

It is the fact that a group of people whose job is to hold other people’s pain decided, without being asked, to build a monthly container for their own. That they named it something soft and oddly cheerful after a color on a calendar. That they bring ankle cream and family crises and the accumulated weight of doing this work in a district that has not always honored it, and they set it down together for a few hours, and then they pick it up and go back.

These are cathedral builders. They do not know the name of the person who will walk through the doors of the finished cathedral. They cannot see the completed structure from where they are standing. They are laying stones. Quietly. Without ceremony. In between the warm transfers and the parent calls and the coats they give away without asking permission.

If you are a district leader reading this and you want to know whether your culture is ready for the transformation you say you want, start here: do the people doing the hardest relational work in your organization have a Pink Tuesday? Have you built it for them? Or have they had to build it for themselves?

And if they have built it for themselves, do you even know it exists?

I left that district tired in the way that good work makes you tired. The kind of tired that comes from being fully present. From letting what people are carrying actually land on you. The good news is I am going back. We are committed to a full year of work together. That kind of tired, the kind that means something, is exactly the kind I want more of.

It has been a while since I was in a room like that. A while since I stepped into an elementary school and heard what is actually happening on the ground. Being back reminded me why I got into this work. Not to write about transformation from a distance. But to be in the room where it is happening, with the people doing the slow, hard, essential labor of building something that will outlast all of us.

To every community school liaison, every family coordinator, every crossing guard, this piece is for you.

You are not support staff. You are the work.

And to the districts and organizations that are serious about this, not the version that looks good in a strategic plan, but the version that requires honest reckoning about what you have actually built and what you have left to the people in the margins to build for themselves, the room is waiting. The work is waiting. And so are the people inside your buildings who have been building Pink Tuesdays on their own for too long.

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Before we get into this week’s piece, I want to take a moment.

It has been one year since we started The Work Within Us community on Substack. One year of videos, essays, Q&A sessions, Problem of Practice conversations, book club gatherings, and honest dialogue about the inner life of leadership. What you all have brought to this space has genuinely moved me. Thank you for being here.

As we head into year two, I am making one change. We are moving from a weekly cadence to bi-weekly. A new piece or video every two weeks instead of every week.

Bi-weekly gives me the space to go deeper, sit longer with ideas, and bring you something more nourishing each time rather than something more frequent. Quality over volume. That is the commitment.

If for any reason this change doesn’t work for you, I want you to reach out directly.

Thank you for a remarkable first year. The best is ahead.

Shawn

They say travel gives you perspective. It widens your view and reveals the assumptions you didn’t know you were carrying. If that’s true, I should have picked some up on my recent trip to Europe. I’m not sure I did. At least not yet.

I was invited to a meeting in Paris at a bold experimental university built to solve the world’s problems. They wanted to know how my work could help youth serving NGOs and government systems. They walked me through campus, and I kept noticing how many rooms looked like workshops or labs where students actually build things. Concrete tables, table saws, 3D printers, spools of wire, sheet metal labeled neatly in French. The founders believe students should build solutions, not just study them.

“We don’t have the best students in the world,” they told me. “We produce the best students for the world.”

On the way to our meeting room, one object stopped me in the hallway. I thought it was a sculpture, maybe an elephant. Up close, I saw it was actually made of hundreds of small, colorful plastic animals, shaped into the outline of an elephant. Weird, I know.

When I asked François what it was, he lit up. “This is how we keep our perspective,” he said.

The piece is built around the old fable of the three blind men and the elephant. Each man touches a different part, the trunk, the leg, the ear, and swears he’s found the whole truth. François explained how they use the sculpture with students. They blindfold them and ask what they’re touching. Some say a tree. Some say a snake. It’s only when the blindfold comes off that they see the whole animal.

I was floored by how simple, and how sharp, that lesson was.

I keep coming back to this in thinking about my work. Most organizations are just a room full of blindfolded people arguing about a leg. The board thinks it’s a tree. The staff thinks it’s a snake. Everybody’s certain. Nobody’s touched the whole thing. And most of what gets called conflict, or culture, or misalignment, is really just people mistaking their grip for the whole animal.

I started noticing it everywhere for the rest of the trip.

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Perspective

Nedra and I had dinner one night at a small mom and pop spot. Quiet, quaint. A group of American tourists sat near us, from Pennsylvania, from what I could pick up eavesdropping.

Maybe I was hungry. Maybe it had been a long day. Either way, the volume of their voices grated on me, and I found myself annoyed by the smug bravado of a couple of balding, big bellied men laughing loud from their guts.

I’m American too. What bothered me most was the fear that this might be exactly who I am, moving through the world with the same confident, thin hubris, blind to my own volume.

But I’m also a Black man from America, and my eyes have seen too much for that comparison to hold all the way. I watched my father work himself raw to put food on the table. I’ve heard mothers whose children were taken by callous cops. I’ve smelled the particular stench of unjust suffering among Black folk. It sticks in your nostrils and never quite leaves.

If you blindfolded me and asked what I was touching on that elephant, I suspect I’d feel something darker, and something more real.

• A noose hanging from a poplar tree.

• A police dog chasing a young Black boy through a Chicago alley.

• A gun leveled at a young father on Staten Island.

Forgive me for going dark today. I’m just keeping it real.

Whatever you’re touching right now, in your organization, your movement, your marriage, your grief, it’s real. It’s not a distortion. It’s not you being too sensitive or too political or too soft. It’s just one part of something bigger than any of us can hold in two hands. Full stop!

You don’t have a communication problem. You don’t have a culture problem. You don’t have a strategic alignment problem. You have an elephant problem. Everyone around your table is certain about what they’re touching, and certain enough to build policy, budgets, and grudges on top of it.

The board member who’s never buried a nephew is touching something real. The staff member who has is touching something else entirely. The funder who calls it impact and the community who calls it survival are both telling the truth.

None of them are wrong. All of them are incomplete. And the leaders who last in this work aren’t the ones with the strongest grip. They’re the ones willing to ask what somebody else is holding, and believe them, even when it costs them their certainty.

I don’t know what the whole elephant feels like yet. I’m not sure I ever will. But I know this. The moment I decide my grip is the only true one is the moment I stop building anything worth building.

So take the blindfold off if you can. Or better yet, leave it on, walk the circle, and go find somebody whose hands are touching something you’ve never felt.

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I’m writing this from a beach bar, laptop neatly placed beside a cold rum punch sweating on the bar. I can smell the ocean, and hear patois in the background among the locals. I shouldn’t be doing this. I know that. I’m on vacation. But here I am.

I’ve snuck away from our hotel room, Nedra taking a well-deserved nap, to find a quiet place to share some thoughts with you about why I’m writing and working during my time off.

It’s really not that complicated. I’m writing now because I feel guilty.

Guilty for ignoring emails despite the out-of-office message. Guilty for missing a meeting I should have attended. Guilty for not following up on a request when I should have. I could go on. But the short version is, I feel guilty for not working sometimes.

Nedra and I had been planning this trip for months, time with family and friends in one of our favorite places in the world. We’re island people. Crystal blue water, sandy beaches, rum drinks all day. It takes me about 48 hours to slide into the slow rhythm of the day, and I love waking up when my body is ready, not when my iPhone alarm jolts me out of my sleep. We don’t schedule things on vacation. We watch the day unfold. A swim, a movie in the Airbnb while it rains outside, a walk that turns into finding a great local restaurant we never would have planned for. We don’t watch the news either, not once, the whole trip.

About three days into the slow days and rum punches, something predictable happens. I start to feel guilty about how good it feels to not think about work. Like my vacationing is some kind of abandonment of the people, the issues, the work I’ve spent my life on. I know, I know, that’s a little crazy coming from a guy who writes constantly about the importance of rest. But I still get that nagging feeling that taking time off is leaving the movement hanging.

I’m not talking about rest, though. I’m talking about guilt. The sense that your actions are undeserving, unwarranted, or just plain wrong.

There is a guilt I feel watching all the workers prepare food, keep the grounds beautiful for guests, clean the rooms. I know that their wages are probably meager, and those who own and manage are probably doing just fine.

Nedra and I talk about this often, usually in the exact moments when we’re enjoying ourselves the most. We’ll be sitting by the water, drinks sweating in the heat, and one of us goes quiet watching the staff move around us, and she’ll name it before I do. She calls it a spiritual injustice. Not guilt, not shame, something more precise than either of those words. It’s the particular ache of feeling genuine joy while knowingly standing inside something that benefits from someone else’s limited options. The feeling isn’t about doubting whether we deserve this moment. It’s about wishing everyone around us had equal access to it. As she always says, “everyone should be able to experience these things should they choose to.”

That distinction matters more than it might seem. A spiritual injustice doesn’t ask you to shrink, apologize for your joy, or cut the trip short. It asks something bigger and more generous than that. It asks you to want more joy in the world, not less of it for yourself.

It’s an accurate read of something real.

But there’s a name for what happens when this feeling stops being about the people around you and starts becoming about you instead.

It’s survivor’s guilt.

We usually think of survivor’s guilt as something that belongs to people who lived through a tragedy others didn’t, the soldier who made it home, the sibling who outlived the accident. But survivor’s guilt shows up in quieter forms too, and leaders in this work carry a version of it almost constantly without ever calling it by name. It’s the discomfort of having made it out. Having stability. Having a beach vacation, a full refrigerator, a body that isn’t in crisis, while the people you’ve devoted your life to are still under attack, still without what they need, still fighting for the most basic things.

If you came up out of the communities you now serve, you know this feeling intimately. It’s not irrational on its face. It’s the natural ache of love stretched across an unequal distance.

Here’s where it gets complicated, though. Survivor’s guilt is rarely just one thing. Part of it is exactly what I described watching those workers, an honest, accurate awareness of inequality that deserves your attention and probably your action. But tangled up inside that same feeling is something else entirely, something quieter and more corrosive. Underneath the honest part is often a private belief about yourself that has nothing to do with anyone else’s suffering at all. The feeling stops being I have something others don’t and quietly becomes I haven’t earned the right to have it.

Undeserved. Unearned. Unworthy. That’s the part of survivor’s guilt that isn’t actually about the people you’re feeling guilty toward. It’s about a private, personal scoreboard you’ve been keeping on yourself, one that demands a certain amount of suffering or sacrifice before you’re allowed to feel good, and one that never quite balances no matter how much you feed it.

This is the part worth separating out, because the two halves call for completely different responses. The honest half, the awareness of real inequality, asks something of you. Maybe it’s tipping generously, staying aware, using whatever privilege you carry for something beyond your own comfort. That part has a use. It can move you toward action.

The other half, the scoreboard, doesn’t have a use at all. It can’t be resolved by donating more, working harder, or cutting your vacation short. None of that satisfies it, because the math was never really about the people you serve in the first place. The math was about whether you, specifically, deserve good things. And that’s a question no amount of output will ever fully answer.

So here I am, on a beach, having just spent twenty minutes untangling why I feel what I feel. The irony isn’t lost on me.

But I think that’s actually the point. Even people who write about rest for a living still have to do this work in real time, on an actual vacation, with an actual inbox piling up. The goal isn’t to talk myself out of every uncomfortable feeling. Some of them are telling me something true. The goal is learning which ones are asking something of me, and which ones are just an old scoreboard I never agreed to keep.

I’m going to close this laptop now, go find Nedra, and order a rum punch I haven’t earned through suffering. I’m going to let that be okay.

Something to Sit With

The next time you catch that tight, low-grade discomfort while doing something good for yourself, don’t push through it and don’t perform past it. Use it. Here’s how.

If it’s pointing toward something real, do something with it that isn’t punishment. Don’t cut the vacation short. Don’t quietly suffer through your joy as a form of penance. Instead, take one concrete action that honors what you noticed. Tip the people serving you like you mean it. Ask the staff their names. If you run an organization, look honestly at your own pay equity before the trip is even over. Spiritual injustice is asking you to widen the circle, not shrink your own place in it.

If it’s the scoreboard, name the debt out loud, then cancel it. Say the actual sentence to yourself or to someone you trust: I don’t think I’ve earned the right to feel good right now. Hearing it spoken usually reveals how irrational it is. Then ask, what would it take for me to believe I’m allowed to have this, without first suffering for it? Don’t rush the answer. But don’t let the question go unanswered either.

Build one practice of unearned joy into your normal life, not just your vacation. This is the part most leaders skip. We treat rest and joy as something that only gets permission once a year, somewhere far away, behind a closed laptop. Pick one small thing this week that has nothing to do with your output. A walk with no destination. A meal you didn’t multitask through. Do it without first checking whether you deserve it.

Ask your team the same questions you’re asking yourself. If you lead people, this isn’t only your reckoning. Notice who on your staff performs constant urgency and never takes their full vacation. Ask them directly what they believe they have to earn before they’re allowed to rest. You might be looking at your own reflection.

You don’t have to resolve this on the beach. I haven’t fully resolved it either. But you can stop confusing the two, and you can start practicing the difference long before your next vacation arrives.

The first is a genuinely provocative argument about what we lose when we strip practices like yoga and meditation from their religious ro…

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My son recently moved to Brooklyn, New York. The move was a long-held dream that finally landed him in a small, one-room studio apartment in Flatbush. Remodeled building, new floors, a small kitchen, a clean white pedestal sink. Even a little balcony overlooking the brick backs of the neighborhood apartments stacked around him.

During my visit, we walked to a local store. I wanted to grab a few things for his new bachelor pad. Pots. Black plates and bowls. A set of forks and a few glasses. But what we noticed during that walk stopped us both cold.

Takai had moved into what felt like another country. Everyone was every kind of Black. Haitians, Jamaicans, Trinidadians, the fragrance from their little restaurants floating into the street. Nearly everyone speaking some form of patois. The whole neighborhood vibrating with an ease you feel in your chest before you can name it.

Takai turned to me and said, “Dad, everybody is black here... It feels good... sorta like I’m supposed to be here.”

Sorta like I’m supposed to be here. That is what belonging feels like when it’s real and unconditional. No application. No performance review. No explaining or justifying his existence to anyone. He arrived, and the neighborhood already knew him. His worthiness was never in question.

To belong to something and to matter is one of the most fundamental ingredients of the human experience. Belonging gives us identity. Mattering gives us purpose. With both, we soar. With neither, we languish.

Over the past month, I’ve had a few conversations about belonging of a different type. These were quieter, more guarded. Hush-hush talks about organizations and leaders accused of mismanagement of funds. Sometimes the narrative had already surfaced in the local newspaper. Other times it was moving just below the radar, the way dangerous things do before they break the surface.

The accusations tend to follow a familiar script: irresponsible leaders, betrayed public trust, funds diverted to lavish homes and personal expenses. In the current political environment, those stories carry a particular undertow. After all, why are we spending money on communities that don’t know how to manage it? Why fund equity work if this is where it ends up?

These stories aren’t just about money. They are about who deserves to belong to the sector, to public trust, to the work itself. Similarly, the attack on DEI and equity funding is not primarily a policy fight. It is a belonging attack. The steady drumbeat of fraud narratives, mismanagement stories, and “wasted money” accusations isn’t just defunding organizations. It is doing something more insidious. It is making the people those organizations serve feel undeserving. It is making the leaders doing that work feel fraudulent. It is severing people from their own sense of worth, one story at a time.

Most leaders respond to a belonging attack with an accountability defense. More metrics, more reports, more proof of impact. The instinct is understandable. But that response quietly accepts the premise that their worth is in question in the first place.

Let me be clear. Some claims of mismanagement and fraud are accurate and deserve to be called out. Full stop. Accountability matters in this work, and pretending otherwise helps no one. But in an environment where every justice-oriented organization is under scrutiny, where the accusations arrive pre-loaded with political intent, we have to ask a deeper question: what is this doing to us inside?

Because leaders who spend their energy proving they are not a fraud have already lost something. They have accepted the frame. And once you accept the frame, you are fighting on terrain designed for you to lose.

The real response is not to defend, not to rebrand, not to produce more evidence of your worth. It is to root.

There is a meaningful difference between a leader running from an attack and a leader rooted so deeply in their work, their people, and their calling that the attack simply cannot find the purchase it needs to take hold. Roots don’t move. They don’t issue press releases to justify their existence. They hold.

Takai didn’t arrive in Flatbush and immediately start building a case for why he belonged there. He arrived. The neighborhood received him. And in that reception, something took root, something no landlord, no policy, no political climate could easily dislodge.

That is the practice this moment is asking of every leader in equity and justice work. Rooting. Returning to the source of why you entered this work before the grant made it official. Returning to the community whose trust authorized your leadership long before any funder did. Returning to what you know, not what you believe, what you know about what your work has meant to real people’s actual lives.

A rooted leader is harder to defund than a well-funded one.

Funding can be revoked. Approval can be withdrawn. Narrative can be weaponized. But roots that grow in the actual soil of community, relationship, and purpose hold in storms designed to uproot you.

Resilience is about bouncing back. Rootedness is about never being fully moved in the first place.

Deepening Your Roots

Before you close this, I want to give you something to do. Not a strategy. Not a framework. An honest, quiet accounting.

Ask yourself these three questions. Answer them without your job title, your organization’s name, or your list of accomplishments:

Who are my people? Not your colleagues, not your network. The people whose presence makes you feel like Takai in Flatbush, like you’re supposed to be here.

Where am I actually rooted? The place, the community, the calling that formed you before the work did. What neighborhood, what kitchen table, what set of hands planted something in you that still holds?

What do I know for sure about the value of this work? Not what the metrics say. What you’ve seen with your own eyes, held in your own hands, what people have told you when no camera was rolling and no report was due.

Write the answers down. For yourself, no one else.

The leaders who survive this moment, and more than survive it, lead through it, are the ones rooted in something the attacks can’t reach. Ones whose sense of worth doesn’t rise and fall with whether the funder approves, the newspaper reports fairly, or the political climate shifts in their favor.

They can defund the program. They cannot defund the roots.

Last weekend I grabbed a rare opening in my schedule and drove down to Cape Cod to catch up on some writing. The slow pace, the lake-side quiet, it was exactly what I needed to sit with some ideas I’d been turning over about uncertainty and what it actually asks of us.

One afternoon I wandered into a coffee shop at just the right time. A torrential storm came out of nowhere, swallowing what had been a sunny, warm afternoon in about fifteen minutes flat. Most folks were caught off guard. I was already seated when they all rushed in, coats soaked, laughing nervously at the sky.

I was sitting at a table with a photograph on the wall above it. Chappaquiddick Island. The name rang a bell, so I Googled it. Turned out to be the infamous location where Ted Kennedy drove his car off a bridge and killed Mary Jo Kopechne. He fled the scene. Let that sit for a second.

I looked up from my phone, and an older white man was standing at my table. Politely, he asked if he could sit. The shop had turned into a rain shelter and every other seat was gone.

“Of course,” I said.

He was in his 80s. His clothes weren’t worn for fashion, more for comfort. His tan windbreaker was soaking wet across the shoulders. I could see grey hair spilling out from under a Consumer Reports baseball cap.

He looked exactly like Bernie Sanders. I’m just going to say that.

We struck up a conversation, and it came out that he lived on Martha’s Vineyard. I can’t remember exactly why I asked him if he was familiar with the Chappaquiddick incident, but I did. He paused, then leaned in close, the way someone does when they’re about to share something they’ve kept filed away for a long time.

“I used to work for Ted Kennedy,” he said. “I was there the night it happened.”

He started to lean in further, like he was getting ready to tell me something not available to the general public, then caught himself. Leaned back. Gave me a half smile.

“That was a crazy night.”

That’s it. That’s all I got.

I wanted to press. I wanted the real story, the details, the weight of what actually happened on that bridge. But he was done. The door had cracked open and closed just as fast. Some things people carry without ever fully setting down.

Our conversation drifted and eventually landed on politics. He leaned forward again, this time with a different kind of urgency.

“I hate that orange, racist bastard.”

I smiled. For my white, non-ebonics readers, he was putting 2 on the 10. Over expressing himself to make sure I knew he was on my side.

Now, as a practice, a habit, or just plain good sense, I don’t discuss politics or my political views with older white men. But he opened the door. And I had nothing better to do than walk through it.

Without getting into all the details, I offered a short, laser-focused critique. Not of Trump. Of us. Of everyone. Of you, me, and my momma.

The problem isn’t Trump, the problem is the underlying ideology that made Trump so irresistible, and the overwhelming disdain for a Democratic Party without balls!

We can remove Trump tomorrow. I promise you there are others, many of them far more competent, far more strategic, lined up and ready to take his place.

So I restrain from simplistic, though fully warranted, critiques of the man. Trump is a symptom. And no cure is effective if you refuse to treat the root cause.

Snap, please.

Here’s what I believe, yall: we have a deep problem in America, and it is not Donald Trump. It is the fact that we have never fully rid ourselves of the idea that some people belong here and others don’t. Period. Full stop. Until we dismantle that narrative at its root, our politics will keep degrading into exactly what we have now. A cesspool of policy, rhetoric, and manufactured rage designed to feed the wealthy while the rest of us argue about who deserves to eat.

He listened. Then he paused. I watched his lips press tight, like he wanted to blurt something out but was holding himself back.

Turns out he was a retired CEO and a former Chief of Staff for a congressman in New England.

Then he said, “I have a little newsletter with about 200 of my friends, colleagues, and college friends. I don’t have any political pull anymore, but I follow just about every bill in congress and ask my folks to call or email someone to vote the right way. That’s about all I can do at 82.”

And there it is.

A confession of a cathedral builder.

He wasn’t on television. He wasn’t headlining a conference or collecting an award for lifetime achievement. He was an 82-year-old man in a wet windbreaker, sending a newsletter to 200 people, tracking bills nobody else in his circle was tracking, asking his friends to make a phone call. Doing the hard work without fanfare, without accolades, without any guarantee he would live to see the day it made a measurable difference. But knowing, in his bones, that it did.

I thought about Mary Jo Kopechne. I thought about what it means to flee the scene of something you caused. And I thought about how often all of us do some version of that, not from a bridge in the dark, but from the harder, slower work of actually facing what we’ve built and what we’ve broken, and choosing differently anyway.

The storm had passed by the time we stood up to leave. We shook hands and he disappeared back into the afternoon, Consumer Reports cap and all. But he left something at that table. A reminder that cathedral building rarely looks like cathedral building while you’re doing it. It looks like a newsletter. A phone call. A stone laid quietly, without ceremony, in the right direction.

So here’s my invitation to you: be Bernie.

Not the senator. The old man in the coffee shop. The one who lost his political pull and found his purpose anyway. The one who stopped waiting for the right moment, the right platform, the right amount of influence, and just started sending the newsletter.

You don’t need more power to do the work. You need more honesty about what the work actually is, and the willingness to do it without anyone watching.

The cathedral doesn’t care about your title. It only cares whether you showed up and laid your stone.

So. What’s your newsletter?

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Someone asked me a question a while back that I keep coming back to.

“My senior leadership team struggles with pivoting from fixing problems to building possibilities. They say it lacks urgency. What advice would you give?”

Here’s what I told them. And here’s what I’m telling you.

Is what you’re doing actually working?

Not “are you busy.” Not “are you solving problems fast.”

Is it producing the real result you want?

Because here’s what I’ve noticed: rapid-fire problem-solving creates the illusion of progress. Throw resources at it. Fix it fast. Move on. It feels urgent. It feels productive. It feels like leadership.

But it’s a sugar high.

And sugar highs crash.

Three Questions Your Leadership Team Needs to Sit With

Don’t rush these. Don’t soften them. Just ask.

One. What does your turnover rate actually look like?

Not the number alone. The pattern. Who’s leaving? Why are they really leaving? What does that tell you about the culture you’ve built?

Two. How well do you sleep?

You. Your team. The people in your organization.

If your leadership culture requires constant crisis, constant problem-solving, constant urgency, nobody’s sleeping. And if nobody’s sleeping, you’re not building anything. You’re managing exhaustion.

Three. Have your decisions produced the outcome you’re actually seeking?

Not activity. Not motion. Not the appearance of progress.

Real outcome.

If the answer to any of these is no, you don’t have a strategy problem. You have a culture problem.

Fear and Frenzy vs. Reflection and Curiosity

Two cultures. Every organization lives in one of them.

The culture of fear and frenzy says: Move fast. Fix it now. Urgency is the highest value. Hesitation is weakness. If you’re not solving problems constantly, you’re not leading.

This culture rewards speed over depth. It celebrates reaction over strategy. It confuses motion with progress. And it burns people out.

The culture of reflection and curiosity says: Slow down enough to understand what’s actually happening. Ask better questions. Build solutions that last. Urgency matters, but so does sustainability.

This culture rewards discernment. It makes space for people to think. It knows that some problems can’t be solved quickly, and that trying to force them into a quick fix makes them worse.

Most organizations say they want the second culture. They operate entirely from the first.

Because reflection feels slow. Curiosity feels indulgent. Building possibilities instead of fixing problems feels like you’re ignoring the fire.

But here’s the truth: if you’re always putting out fires, you never ask why the building keeps burning.

Urgency Is a Drug

It makes you feel important. Needed. Alive. It creates the sense that what you’re doing matters because it has to get done right now.

And some things do need immediate attention. Some fires are real.

But most of what gets labeled “urgent” in organizational culture isn’t actually urgent. It’s just loud. It’s just familiar. It’s just the way you’ve always operated.

The more you operate from urgency, the more everything starts to feel urgent. You lose the ability to distinguish what actually requires immediate attention from what just feels that way because you’ve trained yourself to treat everything like a crisis.

That’s frenzy. And frenzy doesn’t build anything that lasts.

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What Possibility-Building Actually Requires

Here’s why the shift from problem-solving to possibility-building feels so hard.

It requires trust. You have to trust that slowing down won’t make everything fall apart. That your team can hold complexity without needing you to fix it immediately. That sustainable beats fast.

It requires courage. Because the people around you, your board, your funders, sometimes your own staff, will interpret slowing down as not caring. They’ll mistake reflection for inaction. They’ll push for quick fixes because quick fixes feel like leadership.

And you’re going to have to say: No. We’re doing something different. We’re building for the long haul.

It requires humility. Possibility-building means admitting you don’t have all the answers yet. It means sitting with questions longer than feels comfortable. It means resisting the pressure to have a plan before you fully understand the problem.

In most organizational cultures, that reads as weakness.

It’s not weakness. It’s maturity.

The Question Underneath the Question

Do you want to be effective, or do you want to feel effective?

Those are not the same thing.

Feeling effective is easy. Solve problems quickly. Check the boxes. Stay busy. Create the appearance of progress.

Being effective is harder. It requires you to step back. To ask whether the problems you’re solving are actually the problems that matter. To build cultures where people can think, not just react. To resist the sugar high of rapid solutions in favor of the slower, deeper work of transformation.

Your senior leadership is struggling with this pivot because they’ve been rewarded their entire careers for speed. For urgency. For solving.

Now you’re asking them to do something that feels like the opposite.

It’s not the opposite. It’s the next level.

And if they can’t make that shift, the culture they’re building won’t last. The people won’t stay. The outcomes won’t come. And everyone will keep wondering why they’re so exhausted and nothing is actually changing.

So ask them the three questions. And then ask yourself: Are we building a culture of fear and frenzy, or reflection and curiosity? Because only one of those will still be here in ten years.

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I think Sandra must meditate every morning, or exercise, or chant, or something, because being in her presence makes you feel calm, relaxed, and at ease. I suppose that is what makes her such a powerful nonprofit leader in Oakland. Her passion for her work, combined with the ease of her voice, gives weight to every sentence. Talking to her feels more like confession than small talk.

Sandra sat across from me at a coffee shop in Oakland, stirring her green chai long after it had cooled. She had been leading her organization for twelve years. Strong programs. Deep community trust. A board that believed in her completely.

She looked up and said something I have heard in different forms at least a dozen times in the past year:

“They think I can save this. And I know I can’t.”

Federal funding gone. Foundation priorities shifted. Individual donors tapped out. The math doesn’t work anymore, and no amount of strategic pivoting or mission alignment or operational efficiency is going to change that. She has run the numbers every way possible. Explored mergers. Considered partnerships. Pitched new funders. She knows what is coming.

But her board doesn’t know she knows.

They are still talking about her like she is the person who is going to turn this around. Still using language like “this is just a rough patch” and “we’ve been through hard times before.” Still asking her to come to the next meeting with a plan.

And she keeps showing up with plans she doesn’t believe in, because telling them the truth feels like admitting she has failed them, and worse, telling herself that she’s a failure.

That is not a strategy problem. That is a grief problem. A courage problem. A deeply human problem.

And it is one of the most common conversations I am having right now, in coffee shops and on phone calls and in quiet corners after conferences. Leaders who know what is coming and haven’t found the words yet. Leaders who built something real and are now sitting with the unbearable possibility that it might be time to let it go.

Nobody told them this part would feel like this.

Nobody told me either.

How Do You Know When It’s Time to Go?

The sector trains leaders to fight. To pivot. To survive. To find the next grant, the next partner, the next version of the work. We celebrate organizational resilience as though survival itself is the mission. We treat closure as defeat and departure as abandonment.

And so leaders stay. Long past the moment when staying is the right thing. They stay because the sector rewards staying. Because their identity is woven into the institution. Because they don’t have language for what they are actually feeling, which is not failure but something closer to completion.

There is a difference between a rough patch and a closed chapter. One requires strategy. The other requires courage.

The signs are there if you are willing to read them honestly. The funding model is structurally broken and no pivot will fix it. The community you were built to serve has evolved beyond what your organization can hold. The mission has been achieved, or passed to other hands, or absorbed into something larger that doesn’t need your organization’s name on it anymore. You have explored every option with genuine rigor and found yourself back at the same conclusion every time.

Or the hardest sign of all: you are staying for yourself, and not for the mission.

That one is worth wrestling with. Because many of us, if we are honest, reach a point where the organization continues primarily because we do not know who we are without it. And that is a real and human thing to feel. But it is not a mission reason to stay. And the people who depend on your leadership deserve to know the difference.

So here is the question I want to put to you directly, the one I’ve been wrestling with myself: are you still here because the work genuinely needs you in this role, in this organization, at this moment? Or are you here because you haven’t yet found the courage to imagine what comes next?

I Built This. Now I Have to Go.

There is a particular grief that belongs to founders. To the people who started with nothing, who built something from an idea and a conviction and a stubborn refusal to accept that it couldn’t be done. Who hired the first staff member, signed the first lease, wrote the first grant, stayed up until 2am for years trying to hold something fragile and important together until it could hold itself.

When you have built something from scratch, it stops being just an organization. It becomes part of how you understand yourself. The institution and the identity fuse together so gradually that you barely notice it happening. And then one day you find yourself sitting across from someone at a coffee shop, or staring at a spreadsheet at midnight, and the question arrives with a force you weren’t prepared for:

Who will I be when I am no longer the CEO? The Executive Director? The founder?

What will I do with my life if I can’t lead the organization I created?

These are not small questions. They are not questions you can think your way through in a single afternoon. They go to the center of identity, purpose, and meaning in ways that no leadership development program ever quite prepares you for.

I know this because I have lived it. Leaving an organization I spent twenty years building alongside people I love, in a season when the funding was scarce and the hard decisions were many, is not something I would have chosen. And the grief of it surprised me. I had prepared for the difficulty. I had not fully prepared for the silence afterward. The way a role that had structured my days and anchored my identity for two decades suddenly wasn’t there anymore. The second-guessing. The unexpected relief. The unexpected loss. The version of myself that had existed inside that organization, and the question of who I was outside of it.

Nobody told me it would feel like this.

What I can tell you now, from the other side of it, is that the grief is real and it deserves to be honored. The work of separating your identity from an institution you helped create is serious inner work. It takes time. It takes honesty. And it takes the willingness to ask a question most founders never get to ask: who am I when I am not defined by what I built?

The answer, when it comes, is usually more spacious than you expected.

But that same fusing of identity and institution doesn’t only shape how we leave. It shapes whether we allow ourselves to close at all. Because in this sector, organizational failure and personal failure have become the same thing. When the organization struggles, we struggle. When it stumbles, we stumble. So we do what people do when their identity is on the line: we hold on. We fight. We downsize to a point of almost comedic inefficiency, keeping the lights on with a skeleton crew and a wing and a prayer, because closing means something we cannot stomach. It means we failed. Not the model, not the funding landscape, not the political conditions. Us. Closing gets read as a character flaw, a confession, proof that we were not enough. And so we choose almost anything, almost anything at all, rather than let it end.

Closing the Doors Is Not Failure. Sometimes It Is the Mission.

We need to talk honestly about something the nonprofit sector almost never says out loud.

Organizations are not immortal, and they are not meant to be. They are vessels for mission, built for a particular moment, a particular community need, a particular set of conditions. When those conditions change, the honest question is not always “how do we survive?” Sometimes the honest question is “have we done what we were built to do?”

Organizations, like people, have seasons. And one of the most important and least practiced skills in the sector is the ability to read those seasons honestly, without the distortion of survival instinct or personal attachment.

There is a difference between an organization that is struggling and one that has genuinely run its course. Struggling organizations have a problem to solve. Organizations that have run their course have a truth to face. And the inability to tell the difference is where leaders spend years of their lives and enormous amounts of community trust chasing a recovery that was never possible.

An organization has outlived its purpose when the mission it was built to serve no longer requires it in its current form. When the community it was designed to support has developed the power and infrastructure to lead itself. When the model that once worked has calcified and can no longer adapt to what communities are facing right now. When the value it once offered has been absorbed, replicated, or made irrelevant by a changed landscape. When the staff are staying out of loyalty rather than belief, and the board exists to sustain the institution rather than advance the mission. When the honest answer to “why are we still here” has quietly become “because closing is harder than staying open.”

The sector’s deep aversion to organizational endings is costing us. It keeps struggling organizations alive past their usefulness, consuming resources, staff energy, and community trust that could be going somewhere more vital. It keeps leaders in roles they have outgrown. And perhaps most damaging, it blocks the next generation of leaders from bringing their own brilliance to the work, their own solutions, their own particular magic that the sector desperately needs.

I want to be honest about the questions I suspect are underneath all of this, because I’ve wrestled with them myself.

Who is going to do this important work if we close? How will the communities we serve be held if this organization is gone? How will this critical work continue without us?

These are not rhetorical questions. They are real fears, and they deserve real answers. The honest answer is that the work continues. It has always continued. It continued before your organization existed and it will continue after. Through the people you trained. The leaders you developed. The ideas you put into the world that now live in other people’s hands. The community relationships that will outlast the organizational structure.

A well-executed closure, done with honesty and care, is not a defeat. It is one of the most responsible acts of leadership available to you. It protects your staff from false hope. It honors your community with truth. It frees the resources, the energy, and the relationships that have been held inside a struggling structure to go somewhere they can actually do more good.

That is not failure. Sometimes that is exactly the mission.

The Dignity of Endings

There is a way to close an organization that honors what it was. And there is a way to close that burns it to the ground. The difference is not in the outcome. It is in how the leader chooses to hold the ending.

A dignified closure begins with honesty. With telling the board, the staff, the community, and the funders the truth about what is happening and why, in enough time for them to make real decisions about what comes next. It means resisting the impulse to protect people from hard news, because protection that withholds truth is not really protection.

Years ago, my friends and colleagues started a charter school in Oakland. It was a sanctuary for families whose children were struggling in the public school system. We poured our hearts and minds into building something beautiful. Then the funding model changed and we couldn’t raise enough to cover the gap. We had to close, and we needed to let the parents know as soon as possible so they could make arrangements for the following year. I had the glorious task, as a board member, of sharing that awful news with a room full of parents and students. People cried. I felt terrible. That was some hard shit to do.

The grief is real, and it deserves to be held both publicly and professionally. The staff who gave years to this work deserve to have that acknowledged. The community members who built relationships with this organization deserve to be told what is coming and why. The volunteers, the donors, the partners who believed in what you were building deserve honesty about how it ends.

It means releasing without bitterness. That is perhaps the hardest part. When you have poured yourself into something and it still didn’t make it, the temptation toward bitterness is real. Toward the funders who pulled out. The board members who didn’t do enough. The sector that didn’t show up. The political conditions that changed beneath you. That bitterness is understandable. But it will poison your ability to close well, and it will follow you into whatever comes next.

What survives an organizational ending, when the ending is handled with grace, is more than you might expect. The relationships outlast the institution. The knowledge travels forward. The people you developed go on to lead other things. The ideas you put into the world find new vessels. The community trust you built, if you honored it on the way out, often outlasts the organization that earned it.

How you leave is part of what you built. The people who gave themselves to what you created are watching how you hold the ending. They will carry that with them long after the doors close. Give them something worth carrying.

Questions to Carry With You

If you are in the middle of this, or approaching it, or sitting across from someone who is, I want to leave you with a set of questions worth sitting with honestly.

How do you know when it’s time to go, and are you honest enough with yourself to hear the answer when it comes?

Who will you be when you are no longer defined by the role you have held, and are you willing to find out?

What will you do with your life when the organization you built is no longer the container for your purpose?

Who’s going to do this important work, and can you trust that someone will, even if it is not you and not this organization in its current form?

How will this critical work continue without you, and can you make peace with the fact that it will?

What does a dignified ending look like for the people who gave themselves to what you built, and what do you owe them before you go?

These are not questions with clean answers. They are questions for the long walk. But the leaders who navigate endings with the most grace are the ones who were willing to ask them early enough to let the answers actually shape what they did.

Dignity, Sandra, and You

We sat at that coffee shop for a long time. The tea went cold. The lunch crowd came and went.

At some point in the conversation, something shifted. Sandra stopped stirring and set down the spoon. She sat up a little straighter. And she said something she hadn’t said yet, to me or, I suspect, to anyone.

“I think I need to tell them what I actually know.”

Not the plan. Not the pivot. Not the next version of the hopeful presentation she had been building for months. What she actually knows. What the numbers say. What the options are and aren’t. What she genuinely believes is coming.

That is not defeat. That is the most faithful thing she could offer the people who trusted her with something they cared about.

Endings are hard. They are supposed to be. The things worth building are worth grieving when they go. And the grief is real, for Sandra, for me, for every leader who has ever had to walk away from something they gave themselves to.

But here is what I have come to believe, on the other side of my own version of this:

The ending is not the opposite of the mission. Sometimes it is the fullest expression of it. The willingness to close with honesty, to grieve with grace, to release without bitterness, to trust that the work will continue in other hands and other forms, that is its own kind of leadership. Quieter than building. Less celebrated. And sometimes just as important.

Nobody told me that leaving would feel like this.

But I am learning that how you leave is part of what you built. And that the people who trusted you deserve to see you do it well.

Reflection Questions

1. Are you staying in your role because the work needs you there, or because you haven’t yet found the courage to imagine what comes next?

2. What would it mean to close, or leave, with full honesty and full grace?

3. What do the people who gave themselves to what you built deserve from you before you go?

Shawn Ginwright, Ph.D. is a Harvard professor, author, and co-founder of Flourish Agenda. The Work Within Us explores healing centered leadership and the inner life of social change.

We also made an infographic for you! You can see and download it below. I hope it helps.

Shawn

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I recently completed my last class for the academic year.

At the beginning of every semester, I tell my students that our goal is to form a beloved learning community, one where our collective and individual intellectual growth is inherently connected to our emotional growth. Both are required in my courses. Not one or the other. Both.

After our last session, the students organized a dinner at a local pub and I stopped by to wish them well. Walking out, I watched them laughing, sharing stories, embracing each other. They came into my course as strangers. They were leaving as friends.

That, to me, is a good semester.

They will head off into the world now to do good things, I suppose. Every spring I find myself in some version of this moment, watching young people walk toward work that matters. Some are headed to classrooms. Some to community organizations. Some to policy shops or foundations or nonprofits trying to change systems from the inside. They are brilliant, committed, alive with possibility. And they have absolutely no idea what they are walking into.

I have been teaching long enough to know that some version of every cohort will still be in this work in thirty years. And some won’t make it past five.

Here is the thing I have noticed after doing this for a long time: the ones who leave early are usually not the ones who cared least. They are often the ones who cared most, who gave everything they had without ever learning how to stay. That is the part we forgot to teach.

So here is what I tell them now. What I wish someone had told me when I was twenty-five years old, full of fire and absolutely certain I was about to change the world.

You’re Not Going to Save Anyone

I know why you’re here. You saw something broken and you decided you were going to fix it. You believe in justice. You believe people deserve dignity. You believe the world can be different.

All of that is true and good and necessary.

But let me save you about five years of painful learning: you are not going to save anyone.

I came into this work with a cape on. I didn’t know it was a cape at the time. I thought it was commitment. I thought it was love. But looking back, there was a particular way I walked into rooms in my twenties that said, very quietly, “I have arrived. The saving may now commence.”

The communities I was so sure I was there to rescue were largely unimpressed.

And they were right.

The people you are going to work with, the students in your classroom, the families in the community, the young people in the program, they have been surviving systems designed to harm them long before you showed up. They have wisdom, resilience, and strategies for getting through that you haven’t learned yet and probably won’t learn until you stop talking long enough to listen.

Your job is not to save them. Your job is to walk alongside them. To create conditions where they can access their own power. To build spaces where healing is possible. To use whatever institutional access you have to reduce the barriers they face.

That is harder than saving. It is slower. It requires more humility. And it is the only thing that actually works.

Take off the cape. It is heavy and it is slowing you down.

The Work Is Slower Than You Think

You are going to enter an organization or a school or a movement and see exactly what is wrong. You are going to have ideas, good ones, about how to fix it. You are going to be frustrated that the people who have been there longer are not moving as fast as you think they should.

Here is what I want you to understand before you send that strongly worded email or call that urgent all-hands meeting to share your six-week assessment of an institution that has existed for forty years.

The people who have been there longer have tried some version of your idea before. They know which battles are worth fighting and which ones will cost more than they are worth. They are carrying institutional memory, relationships, and an understanding of power that you have not developed yet.

That does not mean they are always right. Sometimes organizations calcify and the new person’s fresh eyes are exactly what is needed. But more often, the resistance you are encountering is not about people being stuck. It is about them knowing something you don’t know yet.

This is cathedral work. You are building something that might take 700 years. And you are showing up for a few years of that timeline, maybe a few decades if you last and if your knees hold up.

Your job is not to finish the cathedral. Your job is to lay stones that the next generation can build on.

I know. That sounds noble and a little deflating at the same time. You didn’t go into six figures of student loan debt to lay stones that future generations would get credit for. I understand. Neither did I.

But here is the reframe that helped me: the stones you lay are still your stones. The program you build, even if it gets renamed and repurposed and expanded by someone who comes after you and gets all the awards, still started with what you did. The student who becomes a teacher who changes hundreds of lives, that chain started somewhere. Maybe it started with you.

Learn to measure your work by what you are building, not just what you are achieving. Make peace with the fact that change is slower, harder, and more fragile than you think. And for the love of everything, stop expecting to see the bloom from the seed you planted last Tuesday.

You Can’t Pour From an Empty Cup. And You Do It Anyway.

Everyone tells you to take care of yourself. Set boundaries. Practice self-care. Don’t burn out.

And you will nod thoughtfully, maybe even take a few notes, and then immediately ignore all of it. Because the work feels urgent and people need you and taking time for yourself feels indulgent when others are suffering.

I did the same thing. For years. Decades, actually. I was a world-class ignorer of my own advice on this subject.

Your depletion does not help the people you serve. Your exhaustion does not make you more committed. Your inability to stop does not make you more effective.

What makes you effective is your capacity to be present. And you cannot be present when you are running on fumes.

Build your sustainability practices now. Before you are depleted. Before you hit the wall. Before the grey sets in and rest stops touching it.

Find your people. The ones who get it, who are doing this work too, who can hold you when you are tired without trying to fix you.

Develop rituals that bring you back to yourself. Movement. Silence. Music. Whatever helps you remember who you are outside of what you do.

And learn the difference between guilt and responsibility. Guilt says you have to fix everything. Responsibility says you have to show up for your piece.

You are responsible for your piece. Not the whole thing.

The System Will Try to Make You Transactional

You are entering this work because you believe in transformation. You want to change lives, shift culture, build something new.

The systems you are entering were not designed for that. They were designed for efficiency, compliance, measurable outcomes, and risk management. They want you to be fast, clean, and documentable.

Your grant report does not have a box for “had a conversation that changed how a young person sees herself.” There is no metric for “the look on someone’s face when they realized they were not alone.” Nobody is asking you to report on the moment a staff member finally felt safe enough to tell the truth in a meeting.

And there will be pressure, sometimes subtle and sometimes explicit, to stop caring about those things and focus on what can be counted.

Resist that.

The most important work you will do is relational. It is the conversation after the meeting. The student who stays after class. The moment when someone feels seen for the first time in a long time. I have watched what actually changes people and systems across decades of this work, and it almost never happens in the deliverable. It happens in the relationship.

That work doesn’t show up in reports. It is hard to measure. It often looks inefficient. And your supervisor might look at your calendar and wonder why you spent ninety minutes with one person when you could have processed twelve.

Hold the relational core anyway. Because if you lose it, you will end up building the same systems you came here to change, just with better branding and a more diverse staff.

Check Your Expectations

Many of us come into this work carrying a vivid, almost sacred image of what justice looks like inside a justice organization.

We picture alignment, integrity, people living out the values they proclaim, a culture that actually feels different from the systems it claims to oppose. We hold that image close, and when the organization inevitably falls short of it — and it will — we are blindsided. Angry. Hurt. Disillusioned in ways that feel almost personal betrayal.

Know this: your expectation of what justice work looks like and your lived experience of it will not always match up.

That gap is not evidence that the work is fraudulent or that you chose wrong. It is evidence that you are doing human work inside human institutions, which are always, without exception, unfinished.

When that disillusionment hits, and it will hit, resist the urge to burn down the house! That is the moment to practice what this work actually requires: the ability to dance with accountability and grace at the same time. To name what is wrong without writing off the people who are also, imperfectly, trying to get it right. The work is messy. The people are messy. You are still on the same team.

You’re Going to Make Mistakes

You will say the wrong thing. You will center yourself when you should have centered someone else. You will miss something important. You will cause harm you didn’t intend.

This is not a hypothetical. This is a guarantee. I am sorry to tell you this. I am also not sorry, because you need to know it going in.

After decades of doing this work, I still get it wrong. I still say something in a room that lands badly, still get feedback I wasn’t expecting, still walk to my car sometimes wondering how I completely missed what was actually happening.

The learning does not stop. The mistakes just get more sophisticated.

Your mistakes are not evidence that you are unfit for this work. They are evidence that you are human, doing human work, in complex situations with real stakes.

What matters is whether you can sit with that. Whether you can listen when someone tells you that you caused harm without immediately explaining your intentions. Whether you can apologize cleanly. Whether you can learn from it and do better next time.

The people who last in this work are not the ones who never make mistakes. They are the ones who develop the capacity to make mistakes, acknowledge them, repair when possible, and keep going without being destroyed by their own imperfection.

And here is a small gift from someone who has earned his mistakes the hard way: the people around you are not waiting for you to be perfect. They are waiting to see if you are real. Mistakes, handled honestly, are one of the fastest ways to become real to the people you are trying to build with.

What I Hope for You

As this semester ended, a few thank you notes arrived from students. They always warm my heart in ways I don’t quite have words for.

One student wrote something I have been reflecting on:

“I feel like this course was sacred, and safe. I will be applying these lessons to my leadership long after I graduate. Thank you for pushing, nudging and requiring us to dream and imagine more boldly the future of our communities.”

I read that and sat quietly for a minute.

Sacred and safe. Pushing and nudging. Dreaming more boldly.

That is the whole thing, right there. That is what this work is actually for. Not the reports. Not the metrics. Not the strategic plans. The moment when someone feels held and challenged at the same time, when they leave more capable of imagining the world differently than when they arrived.

That student doesn’t know yet how far that capacity will travel. The leaders she will shape. The communities those leaders will serve. The children in those communities who will grow up in spaces that were built differently because she learned, in one semester, to dream more boldly.

She may never fully see it. Neither will I.

That is the nature of this work. The seeds we plant don’t always grow where we can watch them. And working without that confirmation, showing up year after year without a clear accounting of whether any of it landed, is its own particular kind of challenge. A quiet one. One that lives right alongside the fatigue.

But what I know, after all the years and all the students and all the seasons of this work, is that the accounting you have access to is never the full accounting. What you can see from where you are standing is not the measure of what you have actually done.

So here is what I hope for you.

I hope you find work that matters and people worth building with. I hope you learn early what took me a long time to accept: that caring for yourself is not selfish, that mistakes don’t disqualify you, that slow is not the same as insufficient.

I hope you build things that outlast you. Programs that keep running. Students who become teachers. Ideas that travel forward in ways you will never fully see.

And I hope, when the grey comes, because it will come, you remember this:

You are not worn down. You are worn in. There is a difference. The fatigue is not weakness. It is what love looks like after years of contact with hard things.

The impact you can’t see is still there. Remember, seeds don’t report back. They just grow.

That matters. You matter.

Now go. Build something beautiful.

We need you for the long haul.

Mixing it up this week. I put out a written piece yesterday and a video today — back to back. If you missed the written piece, the link is below.

Hope you’re taking good care of yourselves. Thank you for being part of this community.

The Future of DEI: Moving From Metrics to Moral Centers

The field of Diversity, Equity, and Inclusion (DEI) is currently facing a deep crisis. From significant budget cuts to the removal of training programs and even the erasure of the words “Diversity, Equity, and Inclusion” from official titles, the work has become increasingly dire.

However, despite these external pressures, the real work of DEI has not died or been decimated—it has simply gone underground.

The Shift to “Underground” Work

Dedicated leaders and organizations are not abandoning their frameworks; they are simply continuing the mission without the external labels or mandates. This “underground” phase is characterized by:

• Action without optics: Leaders are continuing the work because it is their “soul work” and purpose, not for public celebration.

• Title changes: Programs are being rebranded, but their core mission and vision remain focused on inclusion.

• Relational repair: Organizations are doing the hard work of internal healing and mentoring overlooked employees without hiring consultants or using official DEI labels.

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