A different cage is still a cage.
I've been telling the same story for three years. The logistics company, the burnout, the Chipotle parking lot. People love it. That's the problem.
A woman at a bar in Mexico City asked me last month what I did before this. I gave her the whole arc. Seventy-hour weeks building something I didn't love. Sold the company for six figures and felt nothing. Went broke. Delivered burritos at 35 from my childhood bedroom. Rebuilt everything from scratch.
She put down her drink and said, "You should write a book."
I've heard that sentence maybe forty times. And every time, I feel this little pulse of something. Validation. Proof that the worst years of my life were worth it because they make a good story now.
The story gets tighter each time I tell it. Funnier. Better timed. I know where to pause. I know when to drop "I was 35, living in my parents' house, delivering Chipotle." I know the laugh line. I know the exact moment they'll lean in.
I'm not sharing my life anymore. I'm doing a set.
That's the trap. Your origin story becomes your identity. And the more you polish it, the more you need it. Which means you need the old version of yourself to stay the villain forever. The guy who burned himself down for a decade. The guy who missed everything that mattered. You keep him alive in the telling so you can keep being the guy who woke up.
But what that costs you is the present tense. Your most interesting material is always five years ago. The thing happening right now, the quiet mornings, the two hours of work, the surf sessions, the small calm life you actually built, none of it gets airtime. Nobody puts down their drink when you say "I woke up at 9, checked a few numbers, went surfing, ate a fish taco, and read for two hours."
So you skip it. Every time. You jump back to the warehouse. The burnout. The midnight client calls. Because that's where the energy is. That's the version of you that earns attention.
I caught myself last month on a call with a buddy back in California. He asked how things were going. Instead of talking about the week I'd had, which was honestly pretty good, I pulled out a story from the logistics days. Some nightmare about a client calling me at midnight on Thanksgiving and me picking up on the second ring like a damn dog.
He paused and said, "Yeah, you told me that one."
Sat with that for a while after we hung up.
He wasn't being mean. He was telling me something I didn't want to hear. That I'd turned my past into a routine. A greatest hits album I keep playing because I'm scared the new stuff isn't good enough.
You do this too. Maybe not the same story. But you've got one. The failed startup. The year everything collapsed. The relationship that gutted you. And you rebuilt. You're in the good part now. But the good part is quiet. It's Tuesday mornings and steady income and a life that mostly works. And when someone asks what's new, you reach back for the wreckage because the wreckage gets a reaction. The wreckage makes you somebody.
You become a museum of your own worst year.
I've been trying something lately that makes me uncomfortable. When someone asks what I do, I talk about this week. Not 2019. Not the company. Not the Chipotle parking lot. Just this week. Where I surfed. What I'm reading. What I cooked. It feels thin every single time. Like I'm handing someone a blank page.
But it's true. The polished story, the one that kills at dinner, that one stopped being true a while back. Not because it didn't happen. Because the guy it happened to doesn't exist anymore. And I've been propping him up like a puppet every time I need to feel like my life is worth talking about.
The life I have now is quiet and small and good. It doesn't make anyone put down their drink. It won't be a book.
The most dangerous story you tell is the one you can't stop telling. Not because it's wrong. Because it keeps you from noticing that what came after might be the whole point.
— Best, Jose
