Imposter syndrome

I've been running a business for a long time, and it's quite successful — most importantly, it provides for my family — and you'd think I wouldn't still feel like an imposter, but I do. It doesn't make sense to me, but it is what it is. And what it is is unrelenting.

I thought hitting certain milestones would change it — if I could make this thing sustainable, turn it into a real business, or hit $𝑥 MRR, or get 𝑛 customers, then I'd finally feel different.

But the goalpost always moved. It still moves.

What's funny is that it isn't criticism or online comments that get to me, most of the time. It's the self-doubt.

The feeling that I shouldn't have made it this far. The feeling that people don't want to hear what I have to say, or that what I want to say is somehow wrong. That I don't know enough.

That maybe I just got lucky.

But that ignores the work I've put in over the last eight — almost nine — years. Years of blood, sweat, and yes, tears. Being a founder is hard. From the outside it may look easy, but there's literally no playbook. What works for one won't work for another. And you don't even know what will work until after you've done it.

For years, I ignored the 'fail-fast' mantra and just focused on not dying. Instead of succumbing to the enterprise sales dance, I went #nocalls. Instead of expanding head count to cover for me, I redesigned my business so that I could still take time away.

At every step of the way, I doubted myself. If people only knew what I was doing, they'd think I was batsh*t crazy.

"And who are you to tell them to do this too? — you may fail!"

And yet, I haven't failed. In fact, I've succeeded.

(And if I do fail, who cares? People fail all the time. Not everything has to be a success. I've failed countless times over the years.)

But despite the success, I still feel like I have no authority to share "it" with others, much less to tell others to do it. My self-doubt creeps in and tells me that I'm an imposter — that I shouldn't be here.

The self-doubt manifests itself as an unrelenting voice in the back of my head whispering — or rather, shouting:

"Who are you to talk about this?"

This voice used to debilitate me, and it's the reason I didn't share my journey for a long time. It's the reason I left social media for years. It's the reason I didn't share my thoughts on bootstrapping. It's the reason I didn't speak about my thoughts on commercial open source.

Yet even with the success, I still have self-doubt. In fact, if anything, the success makes it worse. The more success, the more impact of being found out — whatever the f*ck that means.

But over the years, I've begun to realize that this voice is lying. The self-doubt is unfounded — irrational. If Neil Armstrong — the first man to walk on the moon — felt like an imposter, maybe it's even normal.

Maybe the imposter syndrome isn't proof that I don't belong. Perhaps, it's a side effect of pushing myself into places I haven't been — into uncomfortable places — into places maybe I do belong.

Do I feel like an imposter writing this post? Yes. And have I trashed similar posts in the past? Yes.

But I won't let that stop me now.

The real risk isn't in being "found out." It's in listening to the voice — and letting it stop me from sharing, from shipping, from doing.

At the end of the day, like most people, I just want to be heard, and I want people to like me. I want to know that what I do has value, because if I'm being honest — right or wrong — my self-worth can get wrapped up into what I build. It's part of me. It's my art.

But waiting for permission — to be told, explicitly, that I belong — is just another way of holding myself back. No one is keeping score. No one is going to tell me I've "earned" the right to speak. I have to put aside the self-doubt and I just have to do things.

Maybe imposter syndrome never fully goes away. Maybe it does, eventually. Maybe I can write about that happening — and how it happened. But it hasn't yet, so this is where I'm at.

Either way, I'm not waiting for it to happen.

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Aside: sometimes when a post of mine hits the front-page of HN, or some subreddit, or gets shared in a newsletter, I'm shocked to hear that people have been following my journey since the beginning. That they look up to me. That I inspire them.

For the longest time, I was unaware other founders — outside of Keygen's customer base — even knew I existed. Nobody ever reached out and told me.

I never wrote because I thought I was an imposter writing into a void.

So if you look up to somebody, or like their writing, tell them!

It may make their year, and help them do things.