You design a life with no roots and then wonder why nothing grows
I've had the same best friend four times this year. I don't talk to any of them anymore.
There was a guy in Lisbon who surfed the same break I did. We'd paddle out at dawn, grab coffee after, sit there for an hour talking about nothing and everything. One of those friendships that feels like it's been going for years even though it started three weeks ago. He told me about his divorce. I told him about the years I lost running my company. Real stuff. Not small talk.
I left for Mexico in November. We said we'd stay in touch. We texted for maybe two weeks. Now he's a name in my phone I scroll past.
Then there was a woman in Oaxaca who ran a small ceramics business out of her apartment. We'd cook dinner together twice a week. She's the one who told me I eat like someone who forgot that meals are supposed to be an event, not a task. That stuck with me. I still think about it.
I left for Bali after six weeks. Same script. Texts for a while. Then silence.
That's the trap. You design a life with no roots and then wonder why nothing grows.
I used to think roots were the problem. When I was running my logistics company, every relationship I had was tied to a place. The warehouse guys. The clients. The girl I was dating who lived twenty minutes from the office. I was pinned. People, obligations, geography. All of it holding me in one spot.
When I sold the company and started moving, I thought I was finally free to find the people I actually wanted. Not the ones proximity handed me. Not the coworkers I grabbed beers with because we clocked out at the same time. Real connections. Chosen ones.
And I found them. That's what makes it worse. The people you meet while traveling are sometimes the best people you'll ever meet. You connect fast because neither of you is performing your job title or your zip code. It's just two humans being honest in a place neither of them is from.
Then one of you gets on a plane.
You've felt a version of this even if you've never left your city. Maybe you had a friend at a job and one of you quit. Maybe you clicked with a neighbor and they moved. Maybe you met someone at a conference and for three days you talked like old friends. Then you went home and the thread went cold within a month.
Connection is easy. Keeping it is the whole game. And the thing about a life built around total freedom is that you're always the one leaving. You're always choosing the next city over the current people.
After the fourth time this happened I caught myself pulling back. I'd meet someone great and somewhere behind my eyes a clock would start. Three weeks, maybe six, then a flight. So I'd keep things lighter than I wanted to. Share less. Laugh more, say less. Not because I didn't care. Because I'd done the math on where caring gets you when there's a departure date.
I turned myself into a tourist in my own friendships.
I don't have a clean fix for this. I'm not writing from the other side. But something shifted. I stopped treating cities like episodes of a show I was binging. Started staying longer. Two months minimum, sometimes three. Not because I have to. Because friendships need the same thing good waves need. Time and consistency. You can't rush either one. You just have to be in the water long enough for something to build.
And I stopped pretending the goodbye doesn't cost anything. It does. Every time. The price of meeting someone real is that leaving them is going to hurt. I spent a year trying to avoid that by not letting anyone in far enough to matter. All I got was a phone full of contacts and nobody to call.
The guy from Lisbon texted me last week. Just a photo of our break at sunrise. No caption. I sat with it for a while.
Some people are worth the plane ticket. Even if you're the one who left.
— Best, Jose
