I keep a list in my phone called “People.” It’s not organized or formatted. Just names, cities, and a sentence or two about each person. Some entries are years old. Some I added last month.
The list started in 2018 in a hostel common room in Berlin, when a woman from Bogota told me something that rearranged my thinking so completely that I was afraid I’d forget it if I didn’t write it down. I didn’t forget it. But I wrote it down anyway, and then I kept writing them down — the people who, through a single conversation or a shared afternoon, became permanent residents in how I understand the world.
Here are a few of them.
Valentina, Berlin
The hostel was in Kreuzberg. One of those places with a bar on the ground floor and dorm rooms upstairs that smelled like laundry and ambition. I was twenty-four, between things, traveling with no particular plan.
Valentina was sitting at the bar reading a book in Spanish. We started talking because she asked if I knew the Wi-Fi password. Within an hour, we were deep in a conversation about careers, specifically about the guilt of not wanting a conventional one.
She was a lawyer in Bogota. Good firm, good salary, her family was proud. She’d taken a month off to travel Europe and was dreading going back — not because the work was bad, but because she’d realized the work was fine. “Fine is the most dangerous thing,” she said. “Bad, you can leave. Good, you enjoy. But fine? Fine keeps you stuck because you can’t justify the exit.”
I’ve thought about that sentence hundreds of times since. It applies to jobs, relationships, cities, clients. The things that aren’t bad enough to quit but aren’t good enough to deserve your time. Valentina put language to something I’d been feeling but couldn’t articulate.
We stayed in touch for a year or so. She eventually left the firm and started a legal consultancy focused on Colombian startups. Last I heard, she was thriving. But even if she’d gone back to the firm, that one sentence — “fine is the most dangerous thing” — would still be the most valuable thing I received from a stranger that year.
Marcus, Bali
Ubud, not the beach towns. I’d gone to Bali partly because everyone told me I’d love it and partly because I was skeptical of anything that many people agree on.
Marcus was German, early fifties, and he ran a small manufacturing company back in Stuttgart. He was in Bali alone for two weeks, which seemed unusual for a fifty-something German businessman, and I said as much. He laughed.
“I come here every year,” he said. “Not for the yoga or the smoothie bowls. I come because running a company makes you hard in a way you don’t notice until you’re surrounded by people who are soft.”
We spent three days together. Not traveling — just eating meals, walking through rice terraces, talking. Marcus had a quality that I’ve since learned to recognize and value: he was genuinely curious about a twenty-something’s view of the world without being patronizing about it. He asked real questions. He listened to the answers. He disagreed when he thought I was wrong.
On our last dinner together, he told me about the year his company nearly went under. A major client pulled their contract, cash flow collapsed, and he had to lay off a third of his workforce. “The hardest part wasn’t the money,” he said. “It was that I stopped trusting my own judgment. Once that goes, everything goes.”
That conversation has come back to me at every difficult moment in business since. Not as comfort — Marcus wasn’t a comforting person — but as a reminder that losing confidence is a more serious threat than losing revenue. Revenue comes back. Confidence, once shattered, has to be rebuilt brick by brick.
Elif, Istanbul
The best cab ride of my life was in Istanbul, which is saying something because Istanbul traffic is a test of spiritual endurance.
Elif was my driver. She was one of the few female cab drivers I encountered in Turkey, and she was immediately, disarmingly funny. Within five minutes, she’d made fun of my pronunciation of Sultanahmet, recommended a restaurant that “only Turks know about” (it was packed with tourists, but the food was genuinely excellent), and offered her opinion on the Turkish economy with more nuance than most analysts I’ve read.
The ride was supposed to take twenty minutes. Traffic made it forty-five. I didn’t mind.
Elif had been a schoolteacher for fifteen years before driving a cab. She switched because the pay was better — which tells you something about teacher salaries in Turkey — but also because she liked the freedom. “In a classroom, every day is the same children,” she said. “In a cab, every ride is a new person. I learn something every day.”
She asked me what I did. I told her about the agency. She asked how many people worked for me. I told her. She nodded and said, “Five people depend on you. Don’t forget that when you’re tired.”
I think about Elif more often than she’d probably believe. The simplicity of that observation — people depend on you, don’t forget it — cuts through all the abstraction of “leadership” and “management” and brings it back to what it actually is: a responsibility to other humans.
James, Cape Town
James was sitting next to me at a wine bar in Stellenbosch. American, originally from Philadelphia, had been living in Cape Town for eleven years. He’d come to South Africa to work for an NGO after college and just… stayed.
“I was supposed to be here for a year,” he said. “But then a year turned into two, and two turned into ‘I bought a house,’ and here we are.”
James had built a life in Cape Town that most people would envy — a small consulting practice, a house in Woodstock, a deep community of friends. But what struck me wasn’t his lifestyle. It was his relationship with the concept of home.
“Americans think home is where you’re from,” he said. “South Africans think home is where you’ve chosen to be. It took me a few years to switch from one to the other.”
That distinction between inherited home and chosen home has stayed with me. I’ve lived in different cities, moved countries, built relationships across time zones. The idea that home is a decision rather than a birthright is both liberating and demanding — it means you have to actively choose, over and over, rather than defaulting to where your parents live.
James and I still email occasionally. Not frequently — maybe four or five times a year. But each email picks up exactly where the last one left off, which is a quality specific to friendships formed in travel. There’s no social maintenance required. Just genuine connection, whenever it happens.
Yuki, Osaka
I met Yuki at a standing ramen bar in Osaka. The kind of place with eight seats, a single chef, and a line out the door. She was standing next to me, and we started talking because the wait was long and the only thing to do was talk or stare at the wall.
Yuki worked for a tech company in Osaka and was exactly one week away from quitting to start her own business — a subscription service for Japanese artisan ceramics. She was terrified and exhilarated in equal measure.
What made the conversation memorable wasn’t her business plan. It was the way she talked about fear.
“In Japan, we’re taught that uncertainty is something to avoid,” she said. “But I realized that every interesting thing I’ve done happened because I was uncertain. Certainty is boring. Certainty means you already know what happens next.”
She said this while eating ramen, casually, as if she were commenting on the weather. But it landed with the force of something that had been thought about for a long time.
I’ve repeated Yuki’s framing to at least a dozen people since: certainty is boring, certainty means you already know what happens next. It’s become something I reach for when I’m standing at the edge of a decision and the safe option is pulling me back.
Why Strangers Matter
There’s a reason these conversations happened with strangers and not with friends.
Friends know your context. They know your history, your defaults, your patterns. When a friend gives you advice, it’s filtered through what they know about you. That’s usually helpful. But it can also be limiting — they reinforce your existing framework because they share it.
Strangers have no framework for you. They respond to what you say in the moment, not who they think you are. And because the relationship has no future obligation — no need to maintain it, no social debt — the conversation can be startlingly honest. You can say things to a stranger you wouldn’t say to a friend, and they can say things back that a friend would hedge.
Travel puts you in proximity to strangers in a way that normal life doesn’t. Not just physical proximity but psychological proximity — the shared vulnerability of being somewhere unfamiliar, the lowered defenses that come with being outside your routine.
I don’t romanticize this. Most conversations with strangers are forgettable. Most hostel small talk is exactly as deep as “where are you from” and “how long are you staying.” But every now and then, the alchemy works. The timing is right, the openness is mutual, and someone says something that lodges itself permanently in your thinking.
The List Keeps Growing
My “People” list has maybe forty names on it now. Some became actual friends — people I see when I’m in their city, people I’d call if I needed advice. Most are just names with a sentence next to them, snapshots of moments that mattered.
I look at the list sometimes when I’m feeling stuck or narrow. Not for answers — none of these people gave me answers. For perspective. For the reminder that the world is full of people thinking about interesting things, and all it takes to access that thinking is being willing to talk to someone you don’t know.
Valentina’s “fine is the most dangerous thing.” Marcus’s warning about losing confidence. Elif’s quiet reminder about responsibility. James’s distinction between inherited and chosen home. Yuki’s reframe of uncertainty.
None of those ideas are mine. They were given to me freely, by people who had no reason to give them except that we were in the same place at the same time and we chose to talk instead of looking at our phones.
That’s the whole trick, really. Choosing to talk.