I’ve Been a CTO. I Still Don’t Always Know What I’m Doing.
Leading with authenticity isn’t a weakness — it’s the only thing that actually works.
Real John here… This week, I’m getting back into leadership/management and a little about my sobriety journey. A little personal this week, and less functional. I hope this opens your mind to what you need to look at and realize you can be surrounded by people and still feel lost and alone. Its ok to feel imperfect but remember we all are perfect versions of ourselves. Ten of Hearts this week, if you know you know.
Side note: I learned a REALLY cool trick this week, and if you work with me, ask me about it. I need to practice, and it is so cool that I know how its done and it still fools me. Ok, sorry, had to share that… on to the newsletter.
Let me tell you something that took me decades to say out loud.
I’ve led engineering teams at multiple companies. I’ve been VP of Engineering. I’ve carried the CTO title. I’ve sat in board rooms, made million-dollar infrastructure decisions, and presented roadmaps to boards who were betting real money on my judgment.
And there have been moments — more than I’d like to admit — where I was sitting in that room thinking: I have no idea if this is the right call.
That’s imposter syndrome. And if you think it goes away when you level up, I’m here to tell you it doesn’t. It just gets quieter. You just get better at managing it.
Or in my case, for a long time, I got better at drowning it out.
The Lie We All Agreed To Tell
There’s this unspoken contract in tech leadership. You project confidence. You speak in certainties. You never let them see you sweat. Because the moment you admit you don’t know, someone in the room will decide you shouldn’t be leading.
So we all walk around performing expertise like it’s a job requirement.
And here’s the thing — it works. Until it doesn’t.
I’ve watched brilliant leaders make catastrophically bad decisions because they were too committed to their own narrative to ask a simple question: “Am I sure about this?” I’ve seen teams lose trust in their managers not because the manager made a mistake, but because the manager pretended they hadn’t. Everyone in the room already knew.
The performance of certainty costs more than the admission of uncertainty ever will.
Getting Sober Forced Me To Meet Myself
I’m sober. I don’t talk about it enough, but I’m talking about it today because it’s directly connected to everything I’m about to say about authentic leadership.
When I got sober, I couldn’t perform anymore. Not because I didn’t want to — but because sobriety has a way of stripping everything down to what’s actually true. The armor comes off. The noise goes quiet. And what’s left is just you, in the mirror, with no way to avoid the conversation.
That’s terrifying. It’s also the most clarifying thing that’s ever happened to me.
For a long time, I had been managing imposter syndrome the way a lot of high-performers do — by staying busy, staying loud, and staying just comfortable enough to not have to sit with the doubt. Getting sober took all of that away. Suddenly I had to actually face the question: do I believe in myself, or have I just been outrunning the question?
The answer, honestly, was somewhere in the middle. And that was okay. Because for the first time, I was finally dealing with what was real instead of what I was pretending.
What I discovered on the other side of that process is that I’m actually pretty good at what I do. Not because I have all the answers — but because I know how to ask the right questions, I know how to build great teams, and I’m persistent enough to keep going when things get hard. That’s not nothing. That’s actually the whole job.
But I couldn’t see any of that clearly until I stopped running from myself.
What Actually Happened When I Led Honestly
When I was leading the engineering team at Obsess, I walked in knowing immersive retail was a new space for me. I didn’t pretend otherwise. I told my team: “Here’s what I know. Here’s what I’m figuring out. Here’s where I need your help.”
We hit over 90% retention on that engineering team for more than two years. In an industry where turnover is treated as a cost of doing business, that number is almost offensive.
I don’t think that happened despite my honesty. I think it happened because of it.
When people know their leader isn’t going to fake it, they stop faking it too. And then something remarkable happens — actual problems get surfaced early. Actual solutions come from the people closest to the work. The team stops managing up and starts building forward.
Sobriety taught me that people can feel authenticity. They can also feel the absence of it. You can’t fake authenticity, at least not for long. Your team knows when you’re performing. They’ve always known. The question is whether you’re going to make them pretend along with you, or invite them into something real.
Imposter Syndrome Is Lying To You About What Leadership Means
Here’s the reframe that changed everything for me: imposter syndrome assumes that “real” leaders have all the answers. But that’s not leadership — that’s just being a know-it-all with a title.
Real leadership is knowing how to get to the answer. It’s being persistent enough to keep asking questions until the problem is understood. It’s being self-aware enough to hire people who are smarter than you in the areas where you’re weak.
I am not a graphic designer, shout out to Alyssa E. who IS one. I’ve never pretended to be. I’ve always hired for that. I’m a problem-solver who can write code in more languages than most people have heard of, and I know how to get a product shipped. That’s my lane. I try to stay in it. And I surround myself with people who can cover everything else.
That’s not weakness. That’s the actual job.
The Authenticity Tax
I won’t pretend leading authentically doesn’t cost you something. It does.
Some people will mistake vulnerability for incompetence. Some rooms will read honesty as hesitation. There will be moments where the polished, confident answer would have served you better politically — even if it was empty.
But here’s what I’ve learned: the people who punish you for being real are not the people you want to build with anyway. The best engineers, the best collaborators, the best humans — they can smell performance a mile away. They’re waiting for someone to just be honest with them.
When you show up as yourself, you attract people who want to work with you. Not the version of you that’s been optimized for a room.
Getting sober made that non-negotiable for me. I don’t have a performance version anymore. This is just who I am. And it turns out, that’s more than enough.
I’ve definitely been separated from friends who didn’t like my authentic-self mainly because they were not ready to face their own truths. That is ok. They are on their journey and our time together has ended.
I am now surrounded by people who support me, encourage me, and laugh with me. That means more and working now is what I’ve dreamed of. I’m helping people get better, solving technical challenges, and meeting so many new people. That is what it is about for me at this point in my life.
So What Do You Actually Do With It?
Here’s what’s worked for me when imposter syndrome shows up — and it still shows up:
Name it. Not publicly in the middle of a board meeting, but to yourself. “I’m feeling like a fraud right now.” Just labeling it takes some of its power away.
Separate feeling from fact. Feeling like you don’t know what you’re doing is not the same as not knowing what you’re doing. Your track record is real. Your experience is real. The feeling is noise.
Ask the question. Whatever question you’re afraid to ask because it’ll make you look like you don’t know — ask it. Ninety percent of the time, three other people in the room had the same question and were too proud to raise their hand.
Build in public. Share what you’re figuring out — in a newsletter, in a team all-hands, in a conversation. When you do, you give other people permission to do the same. That’s how trust gets built at scale.
Face yourself. However that looks for you. Therapy, sobriety, journaling, a long walk, an honest conversation with someone you trust. The imposter voice gets loudest in the dark. Bring it into the light and it loses its grip.
I want to say that again: The imposter voice gets loudest in the dark. Bring it into the light and it loses its grip.
The Bottom Line
You don’t have to have all the answers to deserve your seat at the table. You just have to be honest about which ones you’re still working on.
The most dangerous leaders I’ve met aren’t the ones who don’t know. They’re the ones who don’t know and won’t admit it.
Don’t be that person. Be the one who creates a room where the truth can breathe.
Getting sober taught me that I can do hard things. That I can face uncomfortable truths and come out the other side stronger. That the version of me that stopped running from himself is a far better leader than the one who was always performing.
Your team will build better things because of your honesty. It may fall apart first, but the room you are making is the one you want to be in. I promise.
Now go build something amazing — and stop pretending you don’t know what you are doing, you know exactly how to build it.
John Mann is the founder of Startups and Code, a former CTO, and a lifelong developer who’s been writing code since he was 9 years old. He writes weekly about AI, startups, and tech leadership.