Something you might not know about me: I love and collect children’s picture books.

I don’t mean this in a nostalgic, “I-used-to-read-them-to-my-kids” kind of way. I mean I actively seek them out, I think about them seriously as art and literature, and my favorite museum in the world is the Eric Carle Museum of Picture Book Art in Amherst, Massachusetts — a place dedicated entirely to the proposition that the art inside picture books deserves to be taken off the shelf, hung on a wall, and looked at with the same reverence we give any great painting.

If you’ve never been, put it on your list. I’m serious.

I think picture books are worth collecting and studying for the same reason I think they’re worth writing about here: they carry big truths in small packages. The best ones say in 32 pages what a business book takes 300 pages to get to — and they do it with better art.

Which brings me to Caps for Sale.

Do you remember the peddler in Caps for Sale (written and illustrated by Esphyr Slobodkina)?

He walks through the countryside with a magnificent stack of caps balanced on his head — his own checked cap first, then gray, then brown, then blue, then red caps piled high — calling out as he goes: “Caps! Caps for sale! Fifty cents a cap!”

He is, in the most literal sense, a one-person operation carrying everything he owns on top of his head.

If you lead a small organization — five, ten, twenty, thirty people — you probably recognized yourself just now.

You are the peddler. And at any given moment, you are wearing every single one of those caps.

The caps stack up quickly in small organizations. You’re the visionary and the invoice-approver. The fundraiser and the HR department. The culture-keeper and the person who just fixed the printer again. Unlike leaders of large organizations who can hand a cap to a whole department, you walk around with the whole pile — hoping none of them fall.

This piece is about those caps. Not about how to get rid of them (you can’t, not yet), but about naming them — because a cap you haven’t named is a cap you’re wearing unconsciously. And that’s where the trouble begins.

The Monkeys Stole My Caps (A Brief Diagnostic)

In the story, the peddler sits down under a tree to rest. When he wakes up, his caps are gone. He looks left, he looks right, he looks behind — and finally, he looks up. Every monkey in the tree is wearing one of his caps, looking very pleased with themselves.

Sound familiar?

For small org leaders, the monkeys are everywhere. They go by different names:

•       The urgent crisis that hijacked your strategic planning morning

•       The staff conflict that landed in your lap because there’s no one else to catch it

•       The board member who means well and takes three hours of your week

•       The grant report due the same week as the staff retreat you planned six months ago

•       Your own exhaustion, quietly taking the red cap right off the top

The peddler’s first instinct is to get angry. He shakes his fist at the monkeys. They shake their fists right back. He stomps his feet. They stomp theirs. He shouts “You monkeys, you! Give me back my caps!” — and they shout back in a perfect, maddening echo.

Any leader who has ever tried to out-stubborn a crisis knows exactly how this feels.

Naming Your Caps

Here’s what the peddler knew that we sometimes forget: he knew exactly which caps were his, and in what order they were stacked. He didn’t have to guess. He had a system.

Most small org leaders are wearing six to eight distinct leadership roles on any given day. The problem isn’t the number — it’s that we rarely stop to name them. When the caps go unnamed, they pile on unconsciously. We slip from Visionary to Crisis Manager to HR Director to Finance Committee in the span of a single morning, and we wonder why we feel scattered by noon.

So let’s name them. Here are the caps most small org leaders are carrying right now:

🧢 The Visionary Cap

This is the cap that got you here — the one that sees around corners, imagines what could be, and keeps the mission from becoming merely operational. It’s also the cap that most easily gets buried under the others. Many leaders go days without wearing it, and then wonder why the organization feels like it’s drifting. 

🧢 The Culture Cap

In a small organization, culture isn’t an HR initiative. It’s what you model every single day. When you take a real lunch break, you give everyone permission to. When you laugh at a mistake instead of spiraling, you define how failure is handled. This cap is always on, whether you realize it or not — which means wearing it intentionally matters enormously.

🧢 The Operator Cap

Budgets, systems, processes, the thing that broke, the vendor who didn’t deliver. The operator cap is unsexy and essential. In small organizations, leaders often wear this one too much — it’s task-based, completable, and gives a satisfying sense of accomplishment in a role that is otherwise full of ambiguity. Beware of using it as an escape from the harder caps.

🧢 The Coach Cap

Your staff are not just doing jobs — they’re developing as people and professionals, often in large part because of (or despite) how you lead them. The coach cap asks you to slow down long enough to ask: What does this person need from me right now? Not just what do I need from them. In a small org, this cap might be the highest-leverage one you own.

🧢 The External Cap

Donors, funders, clients, partners, community stakeholders, the board. Small org leaders are often the entire external relations function. This cap requires you to be compelling, credible, and consistent — which is hard to do when you just came from a difficult internal conversation and haven’t had lunch.

🧢 The Stabilizer Cap

When things go sideways — and in small organizations, things go sideways regularly — someone has to be the calm in the room. That’s you. The stabilizer cap doesn’t mean you’re not rattled; it means you’ve learned to be rattled on the inside while steadying the ship on the outside. This is one of the most underrated and underappreciated leadership skills there is.

🧢 The Learner Cap

AI, shifting workforce expectations, changing funding landscapes, new models of service delivery — the world is not standing still for small organizations. The learner cap is the one many leaders drop first when things get busy. It’s also the one that determines whether you’re leading your organization into the future or just managing your way through the present.

The Peddler’s Secret

Here’s the moment in the story that nobody talks about enough:

The peddler doesn’t win by out-yelling the monkeys. He doesn’t climb the tree. He doesn’t call for backup.

He throws his own cap on the ground — and the monkeys, being monkeys, throw theirs down too.

The solution wasn’t force. It was self-awareness.

He knew which cap was his. He knew the order. And when he released his grip for a moment, everything sorted itself out.

For leaders, this translates simply: the goal isn’t to wear fewer caps (at least not yet). The goal is to know which cap you’re wearing right now, and choose it on purpose.

When you sit down for a one-on-one with a struggling staff member, take off the Operator cap. Put on the Coach cap. Give it your full attention.

When you’re developing next year’s strategy, don’t let the External cap drag you into thinking about what funders want. Put on the Visionary cap first.

When chaos erupts — and it will erupt — put on the Stabilizer cap deliberately, so that the Culture cap isn’t transmitting panic to everyone watching.

A Word for Emerging Leaders

If you’re a rising leader — not yet carrying the whole stack, but starting to feel the weight of a few caps — pay attention to this:

The leaders you admire aren’t great because they never drop a cap. They’re great because they’ve learned which cap to reach for, and they’ve made peace with the ones still on the ground.

Your job right now is not to have all the answers. It’s to start naming what you’re doing when you’re doing it. Notice when you’re operating versus coaching. Notice when you’re stabilizing versus avoiding. The vocabulary of leadership comes before the mastery of it.

Give yourself that. It’s how the stack gets built — one cap at a time.

Try This This Week

Before your next difficult conversation, your next team meeting, your next planning session — pause for ten seconds and ask yourself: Which cap am I putting on right now?

Name it. Out loud if you want, internally if that’s more your style.

You may be surprised how much the act of naming changes the quality of what follows.

The peddler walked many miles with all those caps. He didn’t need fewer caps to make the journey. He just needed to know they were his — and to know the order.

So do you.