How I Learn a City
Rolling through 🚲
I grew up in Texas, which means I grew up in a car.
That’s what you do there. Drive everywhere. Windows up, AC on, moving through the world in a climate-controlled box.
I rode my bike around the neighborhood as a kid. But it never occurred to me that a bike could take you somewhere. That it could be transportation, not just recreation.
Then I went to Europe, at 22, and saw people commuting on bikes, I was awakened.
Old people. People in suits. People with groceries. Just part of the day.
Something clicked.
I was 24 in DC when I signed up for my first triathlon.
I’d never really ridden a road bike. But I got a Giant OCR1, and hit the road.
I still remember the first time I hit 30 miles per hour on a descent.
White knuckling the handlebars. Front wheel shaking. Completely convinced I was about to lose control.
I didn’t. But I also didn’t know that yet.
By the time I hit 50+ on Whiteface Mountain in Lake Placid a few seasons later, I felt like I could go 70 and be fine.
That’s what time on the bike does. It teaches you how to hold steady when things get fast.
Somewhere in there, I started dreaming about being a bike messenger. It wasn’t about the job, really.
It was the freedom. The adventure. The no guardrails of it. Being outside the system. Moving through the city instead of past it.
I never became a messenger. I became an endurance athlete instead. But the feeling stuck.
Since then, I’ve learned every city I’ve lived in on two wheels (and supplemented on two feet).
Inner DC was traffic circles and learning how to hold my line with cars. Outer DC was the best kept secret of trail infrastructure in the United States paired with the National Parks.
Austin was long and flat with some occasional undulation. Miles that stretched out and let the mind wander.
Portland was landscape of fantastic natural beauty. Being swallowed by a horizon of trees and mist.
New York on a Citi Bike was urban mountain biking. Dodging potholes, cabs, pedestrians. No car, no train, just weaving through the chaos. Freeing in a way that surprised me.
Now it’s Miami.
Flat. Hot. Infrastructure still catching up.
But there’s the underline—a networked path that’s been here for years, disconnected in places. And now they’re finally linking and modernizing it. South Miami neighborhoods to downtown. Suburban to urban in one unbroken line.
I rode it this morning. An hour from my house to Midtown to meet a friend for a workout.
US 1 most of the way. Past Coral Gables, Coconut Grove, through Brickell, into the heart of things.
The energy shifts as you go. Quiet streets give way to construction cranes. Strip malls turn into towers. You feel the city waking up around you.
In a car, I feel trapped. On a bike, I feel free. I think that’s always been true.
There’s something about the full sensory experience.
The smell of the city. The whiz of the wheels. The way you hear conversations as you pass, music from open windows, the hum of the neighborhood.
You notice things you’d never see from a car. The nooks and crannies. The spaces between the obvious.
Someone once asked me how to really know a place.
I said: meet the people. Go to the spots that have developed over time—the restaurants, the shops, the corners where regulars gather.
But more than that—watch how people interact. How they move through spaces. How the city holds them.
You can’t do that at 40 miles per hour with the windows up.
You have to slow down. Be in it. Let the place come to you.
I think that’s how I learn myself, too.
Not by thinking harder. By moving through. Finding the nooks and crannies. Uncovering what’s been there all along.
The bike just makes it literal.
This morning, somewhere between Coconut Grove and Brickell, the city was just waking up.
And I wasn’t exercising. I was just moving.
That’s when I feel most like myself.
