Dan Koehn.
Let’s play a little game of “three truths and a lie.” And yes, I know it’s usually two truths, but I had three and couldn’t decide which one to cut.
1. I have terrible insomnia.
2. I absolutely love driving for Uber.
3. A job change left my wallet — and my existential near-term outlook — feeling a little light.
4. Santa and the Tooth Fairy crashed my 50th birthday party in October, arm-in-arm, ready to eat some birthday cake.
And so, it began — or, more accurately, began again.
The first time I drove for Uber was in 2015, during a period of seismic shifts in my life. A midlife career pivot had me packing up for Miami and a role best described as “challenging.” That chapter ended with my return to Madison, where family and friends welcomed me back — gainful employment, however, did not. Enter Uber.
I drove for Uber for several years, loving the stories that passengers shared. I found myself weaving the dialogues of strangers into the monologues in my mind. Then came 2020. When COVID shut everything down, so did I, pausing not just the driving but the spontaneous connections with the outside world that had become a quiet comfort.
While I drove sporadically after COVID, it was mostly for a little extra pocket change. Fast forward to December 2024. A job that clearly wasn’t working out gave way to something far better: a return to my dream job, doing work I loved with colleagues I deeply admired and cared for.
But it also came with something else: a sizable decrease in pay.
Sure, I worried about the money — for a day or two. But one sleepless night, I found myself grinning in the dark. The idea was simple, elegant, even. I had a car, endless hours of insomnia, and a knack for chatting with strangers. Why not put it all to use? A few clicks later, my account paperwork was filed, and I was ready to go.
That first night back felt like revisiting an old hobby, rusty but familiar. I eased into small talk with passengers, rediscovering my favorite type of ride: the Dane County Regional Airport drop-off. “Going anywhere good?” I’d ask. The standard reply: “Visiting family.” My follow-up: “Is that good?” Sometimes, it earned a laugh, other times a knowing sigh, and occasionally, an unsolicited family drama download. It’s the kind of response that reminds me why I love this gig.
Before long, my Taos turned into a rolling confessional. A sanctuary for late-night truths. Strangers poured out their lives in the quiet anonymity of the dark. There was the tipsy 20-something, his breakup angst spilling out as unsteadily as his words, seeking advice with slurred sincerity. (Spoiler: I gave it.) Couples bickering in the backseat, their whispered tensions rising as if I weren’t there. And then there was the underage girl who produced a maraschino cherry masterpiece after a wild night on University Avenue. Her friends assured me she was okay. (Spoiler: She wasn’t.)
Every ride reminded me that life, like an overnight Uber shift, is messy, unpredictable and beautifully human.
What started as a side hustle quickly became a classroom. Behind the wheel, I mastered the art of reading the room — or the backseat. Some riders craved silence, while others sought connection, and I adapted. One moment I was an armchair therapist, the next a faux philosopher, sometimes even an amateur comedian. And always, I was learning — about people, about myself, about the quiet magic in brief connections.
Of course, it wasn’t all wit, wisdom and wonder. There were the drunk college kids belting off-key anthems like they were auditioning for The Voice. The front-seat cheeseburger incident — a guy who spilled his meal in the front footwell mid-turn: wrong seat, wrong snack. And let’s not forget the guy who tipped me with what I’m pretty sure were fake $2 bills, delivered with a flourish, as if to say, “You’re welcome.”
But amidst the chaos were moments of unexpected grace. Like the man starting a second career after decades in printing sales, carrying no trace of bitterness. Or the bartender who handed me a portion of his carefully smoothed-out tips — a quiet gesture that spoke volumes.
Driving gave me something else, too: space. Space to think, to reflect, to appreciate. There’s something meditative about cruising through Madison’s streets under the glow of streetlights. I didn’t just think about the pay cut — I thought about my values and the life I wanted to lead.
Resilience, I realized, isn’t about grand gestures. Sometimes, it’s about showing up, cruising through the grind, and finding the beauty hiding in the cracks.
Getting back to the game. As you probably suspected, the lie was number four. Santa and the Tooth Fairy never arrived for birthday cake. But even a lie tells something. Is there something the fib says about the fibber?
Think about it: the stories we tell, the truths we tweak, and the fictions we craft aren’t just about navigating the complexities of life. Often, they’re about survival, connection and even self-discovery.
Every Uber ride is a glimpse into this ongoing game. Passengers step into my car with the version of themselves they want a stranger to see. Sometimes, though, they let raw, unfiltered truths slip, caught in the comfort of fleeting anonymity.
Perhaps life itself is about finding where those lines blur — the moments when truth meets fiction — and how much of ourselves we’re willing to share in those fleeting exchanges. Ultimately, the biggest truth is this: We’re all traveling down life’s winding roads, figuring out which pieces of our story we’re ready to reveal. Maybe that’s the game we’ve been playing all along.
Dan Koehn is a writer, arts critic, and recovering opera singer who also serves on the Isthmus board of directors. He is working on a collection of essays called Driven by Stories.
