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I had a Yale MBA, $1,800 of Yale money to test my startup idea, and somehow still managed to talk myself out of it. This is about that.

So I actually did the thing. Yale had an entrepreneurship program, I applied, got in, and they gave me $1,800 to test a business idea. And it was a good idea — an online course to actually help people get their dream job. I ran the ads, tested the funnels, none of it worked, and instead of figuring out why and trying again, I just stopped. I convinced myself the data was saying something it probably wasn't.

I was scared. I had the idea, the support, the funding, and I still talked myself out of it because I didn't feel credible enough to be the person teaching it.

About 70% of people experience imposter syndrome at some point, and it hits hardest among high achievers, which I find deeply annoying. You rack up credentials and somehow feel less qualified.

And separately, like 40% of people won't pursue a good idea because they're scared of failing. Because all of us overly-credentialed, high achievers see “ready” as a moving target that never actually stops moving.

I've been chasing it for years. I'm done. AI is doing great things for my anxiety (thanks for that), but it's also the reason I stopped waiting and started building. You're reading the result.

If you're sitting on something you keep telling yourself you'll do once you feel more qualified — come do it with me. I don't think that “ready” feeling is coming anytime soon.

Next issue: 30+ ways people actually make money outside their day job (and how I evaluated all of them)

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