The hidden curse of doing one remarkably hard thing is that your brain weaponizes your past success against your future growth.
There's a sketchbook on my desk still sealed in plastic. Bought it three months ago from an art store in Lisbon. Haven't touched it since.
I used to draw when I was a kid. Cartoon characters from shows I watched. Faces of strangers on the bus. My mom's hands while she cooked. I was terrible at it, but I didn't know that yet, and not knowing was the whole engine.
I walked past the store on a Tuesday with nowhere to be, thought I'd pick it back up. That feeling lasted about eleven minutes. Got it home, opened YouTube to find a beginner tutorial, and something in my chest locked shut.
Beginner.
I'm 37. I built a company from nothing and sold it. I make more in two hours a day than most people make at jobs that eat up their whole week. And I'm going to sit here learning how to hold a pencil like I'm in somebody's third-grade class.
That's the trap. You do one hard thing, and your brain decides you're never allowed to suck at anything again. Every new thing gets measured against the thing you already built. Nothing survives the comparison. So you stop starting.
A buddy back in San Diego sold his landscaping business a couple of years ago. Did well for himself. Told me he wanted to try woodworking. Two weeks later, he'd dropped four grand on tools, burned through forty hours of YouTube tutorials, and hadn't cut a single piece of wood. I asked him why, and he said he didn't want to waste the materials.
He wasn't protecting the wood. He was protecting himself from not knowing what he was doing. Because once you've been the guy who knows, going back to not knowing feels like you're losing something you can't name.
I did this with everything after I sold the company. Every idea for what to build next had to pass this invisible test. Is it big enough? Is it worth my time? Will people think I'm moving backwards? I killed projects in the shower before they ever made it to a Google Doc because they felt too small for a guy who'd already had a real exit.
Meanwhile, I was 35, delivering Chipotle out of my Honda, sleeping in my childhood bedroom. So clearly, the standards were doing great work.
You've felt this. Maybe you stopped yourself from learning something because you couldn't justify being a beginner at your age or your income level. Maybe you had an idea that lit you up for ten seconds before your brain ran it through the filter of everything you've already accomplished and kicked it back as not serious enough. Maybe you shelved a project because it wasn't strategic. Because it didn't connect to revenue. Because it was just something you wanted to try, and wanting to try wasn't a good enough reason anymore.
That filter feels like wisdom. Maturity. Standards. It's not. It's fear in a blazer.
Everything good I've ever built started with being genuinely terrible at it. Fumbling. Guessing wrong. Making calls I had no business making. The version of me that didn't know what he was doing was the version willing to try. The version that had already succeeded was the one too paralyzed to look stupid doing something else.
Surfing works like this. Every new break you paddle out at, you're a beginner again. The wave doesn't care about last week. You sit in the lineup and watch and eat shit for a while until the water starts making sense. There's no skipping that part. The guys who try to skip it are the ones who get hurt.
I haven't unwrapped the sketchbook yet. But I'm going to. Some flat morning when there's nothing on my calendar, which is every morning, I'll sit on the balcony and draw something terrible. And my brain will tell me a guy pulling in $25K a month should be doing something more significant than sketching a crooked face on a blank page.
And I'll have to sit there with the pencil and remember that every single thing worth having started exactly like this. No skill. No plan. No good reason to believe any of it would work. Just someone dumb enough to begin.
The sketchbook cost twelve euros. The willingness to be bad at something again is the expensive part.
— Best, Jose
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