Essay 9 . May 5, 2026

There's a phrase I've been working to keep close lately. Not because it's hard to find. Because it can be hard to choose.

The phrase is I don't know.

I'm in the most consequential role of my career. I have a team of people who are exceptional at their parts of the work — parts I will never know the way they know them. And I've had to teach myself, deliberately and against considerable resistance, to say a longer version of those three words out loud. You know this better than I do. Walk me through how you do it here.

Not as an apology. Not wrapped in qualifiers. Just the honest sentence.

It is harder than it should be. Every time.

I learned this lesson once before, fifteen years ago. I learned it badly the first time. And the way I learned it is the reason I'm still reminding myself today.

In 2009, I lost my job in banking. The financial crisis took my career with it, and after a long stretch of looking, I landed somewhere I never expected — as a general manager at Target. A team of four hundred people. A seventy-five-million-dollar retail business. A grocery operation, a pharmacy, a logistics function, a merchandising arm. And, beginning the week I started, a full store remodel on top of it all.

I had spent my career in financial services. I had transferable skills — leadership, people, judgment — and I had said all the right things in the interview. What I did not have was any practical knowledge of how a Target store actually ran.

The doubt found me almost immediately.

It arrived as anxiety, not as thought. A pressure under the sternum that woke me before my alarm and stayed with me through the day. The voice underneath it was not subtle: you don't belong here, you don't know what you're doing, they're going to find out. Predictable, ubiquitous, and somehow no less effective for being so. We have all seen this voice. Many of us have coached others through it. And we still find ourselves visited by it, decade after decade, because predictability does not weaken its grip.

But the doubt was telling me something more specific than that, and I missed it for months.

The doubt was not actually saying I didn't belong. The doubt was saying you don't know this part, and the people around you do. Which was true. Which was, in fact, the simple fact of my situation. I had been hired for what I could become, not for what I already was. The team I now led — my assistant managers, my department leads, the people who had run that store before I arrived — knew the work in ways I would not know it for a long time, if ever.

That should have been easy to say out loud.

It was not.

Early in the remodel, my District Manager came to walk the store with me. This was a normal thing. A District Manager walks the store, asks questions, points at things, expects answers. The General Manager walks beside them.

I had a choice in front of me. I could have asked Jose, my assistant manager, to walk with us. Jose knew the remodel inside and out — every fixture, every timeline, every reason this aisle was where it was. He would have answered every question my District Manager asked before I'd finished hearing it.

I chose to walk alone.

I told myself I was demonstrating something. Initiative. Ownership. That I was the kind of leader who rolled up his sleeves. I was not. I was hiding. I was hiding from my District Manager, who would have respected the honest version. I was hiding from Jose, who would have helped me without hesitation. I was, mostly, hiding from myself.

The walk went the way you would expect. I fumbled questions I should have known the answers to. I covered. I redirected. I made it through, but only barely, and I knew the District Manager knew.

When it was over, I told Jose what had happened. I think I was looking for sympathy, or maybe absolution. What he gave me instead was a sentence I have not stopped hearing since.

I could have walked with you and answered those questions easily.

That was all he said. No edge. No correction. Just a quiet observation from a man who had been ready to help, who had assumed I would ask, who could not understand why I hadn't.

I have thought about that walk many times in the fifteen years since. About what the doubt was actually asking of me, and what I made it mean.

The doubt was asking me to lean toward Jose. I heard it as an order to hide from him.

That is the move, I think — the one I see in myself and in nearly every leader I have ever known. The doubt's content is often accurate. You don't know this part. The doubt's conclusion is almost always wrong. Therefore you must conceal it. The first thought is information. The second thought is isolation. And we mistake the second for the first, which is how we end up walking the store alone when our entire team was waiting to walk it with us.

After Jose's line, things shifted. Not all at once — these things never do — but the door opened. I began asking. The team responded the way teams almost always respond when their leader finally trusts them: with grace, with relief, with what I can only describe as gladness. They had been ready. They had been waiting. The only thing standing between us was my pretending I didn't need them.

I am still practicing.

The role I'm in now is bigger than that one. The people around me are extraordinary. The temptation to perform competence I do not yet have is just as strong as it ever was — stronger, maybe, because the stakes feel higher. The anxiety still arrives in the morning. The voice still tells me I don't belong here.

The difference, fifteen years on, is that I know what the voice is actually saying. It is not telling me to hide. It is telling me, in its blunt and anxious way, that there are others in the room who know things I don't, and that the work in front of me will be better if I let them in.

So I practice. I say the three words. I let the silence after them sit there, because the silence is part of it. And I trust that the people around me — like Jose, all those years ago — have been waiting for the invitation.

Here is what I have come to believe about the doubt.

Your people will not remember whether you knew the answer. They will remember whether you let them help you find it. They will remember whether they felt trusted or held at a distance. They will remember whether the leader who could not yet do their job alone made them part of how the work got done — or whether that leader walked the store without them, and made them watch.

What they say about you when you are not in the room will not be shaped by what you knew.

It will be shaped by what you were willing not to know in front of them.