You master the art of beginning and never learn how to stay
I've lived in fourteen cities in three years and I couldn't tell you my neighbor's name in any of them.
Not because I'm unfriendly. I can walk into a hostel common room anywhere on earth and have dinner plans by sundown. I know how to find the good cafe, the cheap tacos, the morning surf break. Give me a new city and I'll have a routine inside a week.
That's my real skill. Arriving somewhere and making it mine.
What I can't do is stay.
Two months in Lisbon, I had a whole thing going. Coffee every morning with the same three people. A bakery that knew my order. A surf buddy who'd text me when the swell picked up. Then one Tuesday I got a feeling. Restlessness. An itch. Something that whispered you could be somewhere else. By Thursday I was on a plane to Mexico City.
I told myself I was being spontaneous. Living free. But I know what I was actually doing. Leaving before it got hard. Before someone expected me to show up on a bad day. Before a friendship crossed into the kind where someone asks what's actually wrong and waits for a real answer.
That's the trap. You master the art of beginning and never learn how to stay.
A buddy back home has lived in the same town his entire life. Same barber since high school. Same crew he plays basketball with on Wednesdays. He knows the woman at the dry cleaner by name. She knows his kids.
I used to pity him. Genuinely. I'd be sitting on some rooftop in Bali watching the sunset and I'd think about him driving the same route to the same office and feel like I'd won something.
But he's got a thing I don't have. Depth. Fifteen years of the same Wednesday game means those guys know him in a way nobody on this earth knows me. They were there when his dad got sick. He was there when one of them went through a divorce. That doesn't build in two months. That doesn't build when you're already browsing flights by week six.
I ran my logistics company for ten years. Hated most of it. But it was the only thing I ever stayed with long enough to compound. The relationships. The skills. The reputation that came from people knowing I'd still be around in six months. All of it grew from years. Not arrivals.
Now everything I've built is designed to run without me. That's the whole point. But it also means nothing in my life needs me to be anywhere, with anyone, for longer than I feel like. Every room I'm in has an exit door and I installed every one of them on purpose.
You've felt this. Maybe not with cities. Maybe with projects that light you up for three weeks until the novelty fades and you jump to something new. Maybe with friendships that are great until the other person actually needs you and then you get busy. Maybe with every idea you chase just long enough to feel momentum before you pivot to the next one.
Beginnings are clean. Nobody's disappointed you yet. You haven't disappointed yourself. Everything is still just potential.
Middles are where it gets ugly. Where someone has a bad week and needs you to just be there without being interesting. Where the work stops being fun and the only way through is the boring kind of discipline that doesn't feel like anything. Where the city has a rainy stretch and there's no sunset worth mentioning.
I don't have this one figured out. What I'm trying is small and probably dumb. I told myself I'm staying in Ericeira until March. No checking flights. No "maybe Thailand" tabs open at midnight. I want to see what happens when the barista stops asking my order because she already knows. Not because I charmed her in week one. Because I'm still there in month four.
The one thing in my life that was ever worth anything took ten years I didn't enjoy. The good stuff didn't come from showing up. It came from not leaving.
Turns out the hardest thing I've ever tried to build isn't a business or a lifestyle. It's a middle.
— Best, Jose
