I’ve spent a significant chunk of my adult life alone in places where I didn’t speak the language, didn’t know anyone, and wasn’t sure what would happen next.
I don’t say that to sound adventurous. Most of it wasn’t. Most solo travel is logistics and waiting and figuring out where to eat when every menu is indecipherable and you’re too proud to point at pictures. It’s standing in a bus station in rural Turkey at 11 PM, realizing the last bus left an hour ago, and quietly problem-solving your way to a solution that doesn’t involve sleeping on a bench.
But something happens when you spend that much time navigating uncertainty alone. It changes the way you think. And eventually, it changes the way you lead.
The Early Trips
My first real solo trip was Southeast Asia. I was twenty-two. I’d traveled before — family vacations, a semester abroad — but always with a net. Someone to consult. Someone to split decisions with. Someone to blame if things went wrong.
Alone in Bangkok, there was no net. Every decision was mine. Where to stay, what to eat, which bus to take, whether to trust the guy offering a ride. These seem trivial, and individually they are. But collectively, they’re a constant stream of micro-decisions made under incomplete information.
Sound familiar? It should. That’s basically a description of running a company.
I didn’t connect the dots at the time. I was just a kid with a backpack trying not to get ripped off. But those early trips were training something I wouldn’t have a name for until much later: comfort with ambiguity.
Ambiguity Tolerance
In leadership, there’s a concept called ambiguity tolerance — your ability to function effectively when you don’t have all the information. Some people freeze. Some people over-research. Some people make a decision and move.
Solo travel trains the third kind.
When you’re alone in a city you’ve never visited, you can’t wait for perfect information. The restaurant might be terrible. The neighborhood might be sketchy. The train might not go where you think it goes. You make the best decision you can with what you have, and you adjust.
I think about this constantly when I’m running the agency. Should we pursue this client? Should we try this new channel? Should we restructure the team? I rarely have all the information I want. But I’ve made thousands of decisions with incomplete information in foreign cities, and the pattern is always the same: gather what you can, decide, adjust. The cost of indecision is almost always higher than the cost of a wrong decision.
A bad restaurant in Hanoi taught me that. You eat something questionable, you feel rough for a day, and then you’re fine. But if you’d spent two hours researching the perfect restaurant, you’d have wasted the evening. The calculus is the same in business, just with different stakes.
The Loneliness Part
People don’t talk enough about the loneliness of solo travel. The Instagram version is golden hour on a rooftop with a journal. The real version is eating dinner alone at 7 PM on a Tuesday in a foreign city, watching groups of friends at other tables, feeling the full weight of your choice to be here.
I won’t pretend I loved every minute of it. There were evenings — in Bogota, in Tokyo, in a small town in southern Morocco whose name I’ve forgotten — where I genuinely questioned why I was doing this. Where the solitude felt heavy instead of freeing.
But those evenings taught me something that boardrooms and business books never could: how to be alone with a hard feeling and not run from it.
Leadership is lonely. That’s a cliche because it’s true. You make decisions that affect people’s livelihoods. You hold information you can’t share. You absorb stress so your team doesn’t have to. And often, there’s nobody to process it with in real time.
Solo travel didn’t make that loneliness disappear. But it made it familiar. I’d already sat with that feeling in a hundred different cities. I knew what it tasted like. I knew it would pass.
Reading Rooms
Here’s a specific skill I picked up that transfers directly to business: reading rooms without speaking.
When you travel alone, you develop a heightened awareness of non-verbal dynamics. You learn to read a cafe before you sit down. You learn to gauge a taxi driver’s mood before negotiating a price. You learn to tell the difference between a friendly approach and a setup.
You do this because you have to. Without a companion to confer with, your own observation is all you’ve got.
I use this skill in every meeting. Watching body language when a client hears a price. Noticing when a team member’s energy drops during a strategy session. Sensing the moment a negotiation tips from productive to adversarial.
Most people in business are so focused on what they’re going to say next that they stop watching what’s happening in the room. Solo travel broke that habit for me. When you spend weeks in places where you don’t speak the language, listening with your eyes becomes default.
Patience as a Strategy
In Marrakech, I once spent an entire afternoon buying a rug.
Not because I particularly wanted a rug. But because the shopkeeper invited me for tea, and the tea became a conversation, and the conversation became a second tea, and by the time we got around to talking about rugs, I’d been there for two hours and it felt like the most natural thing in the world.
In Western business culture, we’d call that inefficient. Two hours for one transaction? We celebrate the quick close. The efficient meeting. The 30-minute deal.
But the shopkeeper in Marrakech understood something that took me years to learn: patience is a strategy. The longer we talked, the more I trusted him. By the time I bought the rug, I didn’t negotiate nearly as hard as I would have if he’d pitched me cold. And I walked away feeling good about the purchase, not pressured.
I think about that rug seller more than I think about any sales book I’ve ever read.
When I’m working with a prospective client now, I don’t rush. I don’t push for the close. I ask questions. I listen. I let the relationship develop at whatever pace feels natural. Some of our best client engagements took months to formalize. The ones I pushed for quick closes? Those are the ones that churned.
Confidence Without Certainty
The biggest shift solo travel created in how I lead is this: I became comfortable being confident without being certain.
Those two things — confidence and certainty — look similar from the outside but are fundamentally different. Certainty means you know the answer. Confidence means you trust yourself to find it.
When you navigate forty countries alone, you develop an almost irrational trust in your ability to figure things out. Not because you’re particularly smart or resourceful, but because you have a track record. You got out of that situation in Istanbul. You found your way in rural Japan without GPS. You survived that overnight bus in Bolivia.
Each solved problem adds to a mental library of “I’ve handled worse.” And that library is what I draw from when the agency faces something new. A client crisis. A strategic pivot. A market shift. I don’t know the answer in advance. But I’m confident — genuinely, not performatively — that I’ll figure it out. Because I always have.
That kind of confidence is magnetic in a leader. Teams can feel the difference between a leader who’s pretending to have answers and a leader who’s genuinely comfortable not having them yet. The former creates anxiety. The latter creates trust.
What I’d Tell My Twenty-Two-Year-Old Self
I’d tell him that the discomfort is the point. That the night you spend lost in a city you can’t pronounce is worth more than the night you spend in the hotel with the good Wi-Fi. That every moment of confusion and solitude and low-grade fear is building something you won’t be able to name for years.
I’d tell him that leadership isn’t about having answers. It’s about being steady when there are no answers. And that steadiness — that particular brand of calm under uncertainty — doesn’t come from business school or management training. It comes from the accumulated experience of navigating the unknown, alone, and coming out the other side.
I’d tell him to keep going. To take the weird route. To eat the questionable street food. To say yes to the invitation from the stranger.
And I’d tell him to pay attention. Because every city, every misstep, every quiet dinner for one is teaching him something he’s going to need later.
He just doesn’t know it yet.