If you’re like most members of the Essentialist CEO Collective — smart, experienced experts who are damn good at what they do and eager to figure out how to earn what they are truly worth — you deal with imposter syndrome.
Maybe not all the time, but it comes up. And it sucks. But it doesn’t have to.
So give me a minute to go down a bit of a story tangent (you know how I roll) so we can talk about how to make it work for you, not against you.
In 2017, a friend named Mickey Bergman — an international negotiator I'd met through a trip he'd organized to Cuba, a delegation of American business and nonprofit people meeting with Cuban entrepreneurs — introduced me and my colleague David Ewald to a woman building the mentor and lecturer roster for a startup accelerator in Beirut.
The program was part of something historic: the first-ever partnership between the United Nations and a startup accelerator. They'd recruited a cohort of social impact startups from Lebanon and the surrounding region, and they'd identified a gap. Their founders needed go-to-market strategy guidance the local ecosystem couldn't fully provide. So they were bringing people in.
Mickey thought of me and David. He made the call.
(I've written about how this whole trip came together in much more detail before — if you want the fuller version, it's here. But what I want to focus on today is the moment I almost didn't go.)
When I heard about it, my immediate instinct was to say no.
At the time, I was head of marketing for an early-stage startup. I'd only been doing marketing for a few years. Other than my work as an employee, I hadn't worked with other startups — I'd never mentored or coached a company through anything.
These were UN-backed startups solving real problems in a part of the world I'd never worked in. Who was I to show up and tell them how to build a brand or go find customers?
I went back and forth on it. For a while, "no" felt like the responsible answer.
And then I looked down at my arm.
I have a tattoo — five words: throw off the bow lines.
They're from a longer quote that has been one of my guiding principles for a long time.
Twenty years from now, you'll be more disappointed by the things you didn't do than the ones you did. So throw off the bowlines. Sail away from the safe harbor. Explore, dream, discover.
Standing there wavering about Beirut, I came back to it: I was more likely to regret not going than going.
So I went.
David and I led workshops. We did one-on-one mentoring sessions with every single founder in the cohort. We gave talks to the broader entrepreneurial community in Beirut.
I got incredible feedback. People actually valued the work I did with them!!!
On the flight home, I had one of those rare moments of total clarity — oh my God, this is what I want to do. That trip is, in a real way, the reason Essentialist CEO exists.
About four or five years later, I got a LinkedIn message from one of the founders I'd worked with. His company, Bildits, had just been acquired and was being called a success story in Lebanon. He wanted me to know:
Imagine if I had said no to that trip simply because I felt like an imposter.
Here's what I've been sitting with since then — and what I keep coming back to with my clients, and what came up multiple times on our Collective call this week:
Imposter syndrome doesn't show up when you're playing it safe. It doesn't arrive when you're doing something familiar, when you're staying inside what you already know, when everything feels comfortable and proven.
Imposter syndrome shows up when you're growing.
Which means — and I want you to really let this land — feeling like an imposter is a signal that you're doing something right.
I said something to the group this week that I haven’t talked about in a while. For years, if I hadn't felt imposter syndrome in a while, I knew I was stagnating. Playing it safe. Not stretching.
The absence of it was the warning. And I’ve learned, that its presence is a sign that I’m on the right track.
If you’re like most of the brilliant entrepreneurs I work with, you are doing something you've never done before. That’s the nature of being an entrepreneur.
Some of you spent decades building expertise inside a company, and now you're bringing that expertise out on your own.
Some of you have been building your business for years but are pivoting — a new offer, a new audience, a new system, a new way of working.
In both cases, the feeling is the same: I've never done this before. Who am I to say I know what I'm doing?
This is one of the most common things that comes up in the Collective. Not occasionally — CONSTANTLY. Because everyone in that room is actively stretching themselves into something new.
This week it surfaced multiple times across our hot seat session. A member said something I wrote down immediately: "I know stuff. I just don't KNOW I know stuff."
That is imposter syndrome in a sentence.
The Diagnostic: One Question
When imposter syndrome hits, stop and ask yourself this:
Am I worried about my ability to actually do the work — or am I worried about what other people will think?
These feel identical from the inside. They are not the same problem.
If you're worried about doing the work — if you genuinely don't know how you'll complete the engagement, what process you'll use, whether you have the skill required — that's real data. It's a solvable problem. You need more information, a resource, a process, maybe a collaborator. Name the gap and address it.
If you're worried about other people's opinions — about being questioned, found out, judged, dismissed — that's imposter syndrome. It's internal. It's your nervous system responding to growth by pulling the alarm. And it requires a completely different response, because there's no information to act on. There's only a story to work through.
Most of the time, when you ask yourself this question honestly, you'll find it's the second one. Most of the time, you actually know how to do the work. What you don't trust yet is your right to be doing it at this level, in this new form.
That distinction matters a whole heckuva lot.
The Protocol: What to Do When It's Imposter Syndrome
1. Ground yourself in what you actually know.
This is what the positioning work I do with clients in the Collective is really for — and I don't think most people realize it when we start. When we spend time excavating your stories, your hard-won lessons, your lived insights from years of doing this work, we're not just building marketing. We're building the foundation of conviction.
So that when the doubt shows up, you have receipts. Not borrowed credentials. Not inflated claims. Your actual experience, your actual wins, the things you've genuinely done and learned.
Your expertise isn't made up. It came from somewhere real. When the imposter voice gets loud, go back there.
2. Don't white-knuckle it alone.
I made the decision to go to Beirut by going back to something I already believed that I would regret NOT going.
But here's what I didn't know until later: when I mentioned to Mickey and David that I'd almost said no, they were baffled. Both of them.
They told me they would have done everything in their power to convince me if I'd tried to back out — that it hadn't even occurred to them that I'd question whether I belonged there, because they didn't question it for a second.
They saw something in me that I couldn't see in myself. That's the thing about imposter syndrome — it's almost always invisible to the people around you who know your work. The doubt feels enormous and obvious from the inside. From the outside, it's usually nowhere to be found.
This is why you need people around you who are doing the same thing you're doing — building their own businesses, navigating their own versions of this — who can reflect back what they actually see in you.
Not cheerleaders who tell you you're amazing no matter what. People who tell you the truth with kindness. People whose opinion of your capability you can borrow when yours runs out.
One of our members brought her imposter syndrome right into the hot seat today and named it out loud. And within minutes, the rest of the room was nodding. Multiple people in completely different businesses, at different stages — feeling the exact same thing. She worked through it by bringing it into the open, not spinning her wheels all alone.
3. Talk to yourself the way you'd talk to a friend.
Someone on today's call said something I'm going to be quoting for a long time: "We need to talk to ourselves like we talk to our dogs."
Try this: if a friend came to you with exactly these worries — her specific doubts, her specific fears — what would you say to her? Take thirty seconds and actually answer that question.
You'll immediately hear how hard you've been on yourself. The things we'd never say to someone we love, we say to ourselves constantly and without blinking. The reframe isn't about toxic positivity. It's about applying the same generosity inward that you give to everyone else automatically.
The next time imposter syndrome hits — and it will — don't treat it as a verdict. Treat it as a signal.
Ask the question. Figure out which kind of doubt you're actually dealing with.
If there's a real gap, close it.
If it's imposter syndrome — and it usually is — go back to what you know is true. Reach out to someone you trust. Talk to yourself the way you'd talk to someone you love.
And if you haven't felt it in a while? Check whether you've been playing it safe. The bowlines aren't supposed to stay tied.
In love, growth, and throwing off the bowlines,
Kasey
P.S. If imposter syndrome is something you're navigating right now, consider joining the Collective. I promise you are not the only one — and the room is safer than you think.