I chose safety over aliveness
I built my freedom by being willing to lose everything. Now I won't risk a damn thing to keep it alive.
A buddy asked me last week why I don't start another company. I told him I like my life the way it is. We both knew I was full of shit.
The truth is I'm afraid. The guy who dropped out of college at 19 and started a logistics company with $800 and a used van is now scared to test a new price on a digital product because what if it drops conversions by two percent. That's where I am. That's who I've become.
That's the trap. You build freedom by being reckless enough to bet on yourself when you have nothing to lose. Then you get the freedom. And suddenly you have something to lose. So you stop betting. You stop building. You maintain. You protect. You check the dashboards to make sure nothing moved instead of trying to make something move.
When I was 22 and running my company out of my parents' garage, I said yes to everything. Contracts I didn't know how to fulfill. Routes I'd never driven. Clients who were probably going to stiff me. I didn't care. The worst that could happen was going back to being broke. I was already broke.
That willingness is what built the thing. Every good decision I made in my twenties came from having nothing worth protecting.
Now I've got three income streams pulling in 20 to 25 grand a month. They work. They're automated. They don't need me except when something breaks. And I treat them like they're made of glass.
A woman I met at a coworking space in Lisbon a few months back was telling me about a business she was starting. She had maybe two months of savings. No safety net. No backup plan. She was terrified and she was doing it anyway. I sat there listening and realized I couldn't remember the last time I did something that scared me. Not a wave that was a little overhead. I mean something where I genuinely didn't know if it would work.
She reminded me of myself at 22. And that pissed me off more than it should have.
You've done this. Maybe you found a pricing model that works and you won't test a new one even though you suspect there's more on the table. Maybe you have a client roster that pays reliably and you won't pitch anyone new because rejection might crack the story you tell yourself about having it figured out. Maybe you had an idea that lit you up for the first time in months and talked yourself out of it by Wednesday because the risk didn't justify the math.
The math will never justify it. That's the point. The spreadsheet will always tell you to protect what's working. The spreadsheet doesn't know that protecting what you have is how you slowly stop being the person who built it.
I turned down a partnership opportunity this summer. Good terms. Interesting product. Would've meant building something new with someone I trusted. I spent four days running the numbers and said no. Not because it was a bad deal. Because it would've introduced uncertainty. The possibility that something in my quiet little setup might need to change.
I chose safety over aliveness. And I told myself it was maturity.
There's a guy I see at the break most mornings. Maybe mid-twenties. He paddles for everything. Waves that are too small, waves that are closing out, waves that are clearly not his. He eats shit constantly. Wipes out, paddles back, goes again. Some mornings I watch him from the lineup thinking he needs to learn to wait, read the sets, pick his spots.
But he's catching more waves than I am. Because he's out there trying while I'm sitting on my board calculating which ones are worth the effort.
I don't know how to get that version of myself back entirely. But I think it starts with one decision this week that doesn't come with a guaranteed outcome. Not a big swing. Just something where I don't already know what happens next.
The person who built the thing you're so busy protecting was never afraid to lose it. Keep protecting long enough and you'll lose him instead.
— Best, Jose
