In Transit: Part 05
The Company You Keep
There's a specific kind of laughter that happens when five people who've known each other for a while are sitting around a table, and someone says something that sends everyone into hysterics - except you. You're laughing too, of course, because the energy is infectious and everyone is lovely and welcoming. But there's a half-beat delay. A small gap where you're watching them collapse into each other, referencing something from two winters ago, some inside joke that's been polished smooth by retelling, and you're on the outside of it. Not excluded, just... new.
I felt it in Bansko, a small ski resort town in Bulgaria. Two weeks with a boy I'd met in Egypt and his tight-knit community - people who'd spent the last two years building a language of shared moments I'd never witnessed. They were generous with their space, warm in their inclusion, but I could sense my place at the edges of their circle. The awareness that I was visiting someone else's history, a guest in their accumulated context. It wasn't bad. It just was.
And it made me miss my people in a way that felt urgent.
The thing about building a life in motion is that you're constantly negotiating what connection even means. You meet people in passing, in pockets of time that feel enormous when you're in them and tiny when you look back. Sometimes you know immediately. Sometimes it takes years to circle back. And sometimes, the people who know you best are the ones who knew you before you ever left.
I think about Gabe standing in front of that restaurant in Cartagena, and how I recognized him before my brain caught up to the fact that it was actually him. We'd been obsessed with each other once, best friends back in San Francisco, before I moved to LA in 2019 and we just... stopped talking. Not because of anything, just because proximity makes things easy and distance makes them optional. We still followed each other on Instagram, double-tapping each other's stories like friendly ghosts.
But then I posted that I was in Colombia, and he was too, and suddenly we were standing face to face in the warm Cartagena evening, and it was like absolutely no time had passed. His demeanor hadn't changed - still that same easy grin, still those same attentive eyes when he listened. We had so much catching up to do. Me, a year and a half into nomading. Him, fresh out of firefighter probation, about to propose to his partner, who was someone I'd never even met.
We spent the next few days together, me with his firemen friends, him with a couple of mine, wandering this new country like we were excavating an old friendship. I keep thinking: if I'd never started traveling, if I'd never had the urge to go to Colombia, would we have found our way back to each other? Or would we have stayed friendly ghosts forever?
Then there was Calvin.
I met him through a solo traveler app, and I didn't know what to expect. I was alone in Okinawa, and we'd agreed to meet for a drink, and I was bracing for that awkward initial small talk, the feeling-each-other-out phase that usually comes with meeting strangers.
But we clicked immediately. Like, immediately. It felt like we were already friends, like we were just picking up a conversation we'd started months ago. He was a singer too, and we bonded over music in that quick, shorthand way you do when you find someone who speaks your language. We decided to find a karaoke bar. The first two were closed. The third was a tiny hole-in-the-wall place, and we sang our hearts out until they kicked us out at closing.
The next few days unfolded just like that: easy, silly, free. We walked around American Village, drank on the waterfront, went to this wild magic show. Then we drove to another island and biked around it in a thunderstorm. I remember the rain coming down in sheets, absolutely drenching us, and on any other day I might've been annoyed, but we were laughing so hard we could barely pedal. It felt like nothing else mattered. Just the storm and the movement and this ridiculous, joyful freedom.
He went back to Germany, and I left for San Diego. We haven't seen each other since, and we don't talk much, but I added him to my close friends story on Instagram because he's someone I want to keep in my orbit. I know if we ever cross paths again, we'll pick up exactly where we left off.
And lastly, Rachel.
I met Rachel six years ago when we worked together at a Starbucks in LA. She's always been a good friend - reliable, dependable, someone I could count on. But it wasn't until she came to visit me in London this past fall, on her first international trip, that I understood what it meant to have a friendship built on shared history and depth.
The moment I saw her on my doorstep, I felt like I'd been transported back to California. I felt like I was home.
We didn't do a terrible amount while she was there. We walked along the canal every morning, the air crisp and a little cold, our breath almost visible in front of us. We went to Batch Baby for coffee, stopping at the same spot on the corner where the light hit just right. We ate at the close-by arepa place. We cooked in the kitchen, and in my head, I kept calling the neighborhood "ours." My stomach hurt so many times from laughing too much.
It was only a week, but it mattered more than I knew how to articulate, and it was because Rachel has known another version of me - the LA version, the restless version who couldn't figure out what she wanted. And now she was here, meeting this new evolved version, the one who'd been on the road for close to two years and she still knew me. I didn't have to explain myself. I didn't have to perform. I could just be.
When she left, I cried. Not just because I'd miss her, but because I realized how much I'd needed that. How much I'd needed to be in the presence of someone who held my history, who could see all the layers at once.
Here's the truth I keep coming back to: this lifestyle is only worth it when you have that kind of connection. There's a reason so many digital nomads feel lonely, and it's because they're lacking people in their lives who make them feel truly seen and truly known. When you meet people on the road for a blip of time, they only get to know a layer or two of who you are. And that's okay - some of those connections are beautiful and brief and exactly what they need to be.
But the ones that last, the ones that matter, require intention. They require showing up, again and again, even when it's not convenient. They require saying, "When will I see you next?" instead of "See you around." They require effort that feels easy when you're in one place and Herculean when you're constantly moving.
It's easy to get caught in the current. To keep chasing the next city, the next experience, the next version of yourself. But when you find your people - the ones who laugh with you until your stomach hurts, the ones who make it feel like no time has passed when you see them, the ones who show up on your doorstep and bring home with them - you hold on to them. Because they're what make this whole thing worth it.
I think about Bansko, sitting in that room full of lovely people, feeling the weight of my newness, aware of all the context I didn't have. And then I think about walking along that canal with Rachel, the word "ours" hanging in the cold London air, my stomach aching from laughter.
Both are true, and both matter.
Because one reminds you what you’re searching for.
And the other tells you when you’ve found it.
This is the fifth post in In Transit, a series exploring the messy, non-linear reality of building a life while constantly moving. Last month, we reflected on loneliness and the quiet cost of life in motion. This month looks at the people who anchor us, the fleeting connections, and the ones who hold our history.
Have you ever felt caught between new connections and the pull of the people who really know you? We’d love to hear how you navigate it. We’re figuring this out together.
Next month’s piece explores why belonging might be the scariest kind of freedom.
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