A collection of shared experiences with the City of Chicago
More than a hundred true stories from 5 years of driving Uber and Lyft in Chicago — what people tell me, what they tell each other when they forget I’m there, and what happens in between. Some are funny. Some are hurtful. Some are life-changing. You won’t know which is coming next. Neither did I.
Sometimes they talk to me. Sometimes they talk to each other and forget there’s anyone else in the car — two friends in the back working something out, a family in from a rural town halfway across the country, or halfway around the world. Either way, I’m right there.
For 5 years now I’ve been writing it down — the conversations, the arguments, the things said to me and the things said near me. A hundred and five so far, and I’m still driving.
It isn’t just a book of crazy Uber stories. It’s that too — you don’t drive here this long without collecting them, and that’s usually what makes people lean in when I bring it up. But it’s a good deal more than anyone expects going in.
I grew up in Chicago. Grew up with Chicago. And you don’t spend years driving a city the rest of the country talks about without noticing how little the talk has to do with what’s actually in the car. What’s in the car is people being people — funny, generous, contradictory, worn down, kind. The same as any other city in America. The same as anywhere else, honestly.
The people in these stories aren’t specimens I observed. I’m in them too.
She spent the first ten minutes roasting my car — the dent, the carpet, all of it. Twenty years in the military and she still laughed like that. By the drop-off we were somewhere else entirely: greed, God, and the devil.
She got in researching something for her business and got out knowing about tribal rolls, and how many of them were destroyed, and who that cost. We spent the rest of the ride on a harder question — how do you keep your integrity and still work for the man?
Twenty-five minutes and a string of wrong addresses before I found him. He got in mid-thought, already going about the mayor of Detroit and how the mafia was a different thing altogether. His friend tipped forty dollars.
He couldn’t remember much of anything — except the exact street Northeastern Illinois sits on, and every punchline he’d ever learned. Red birds have blue babies. Blue birds have red babies. What bird has no babies?
She taught yoga, and she talked about how all of us are connected like it was simply a fact she’d checked. I talked her ear off. She stayed calm the whole way. I still owe her a first class.
… and a hundred more.
I grew up in Chicago — grew up with it, really. I’ve been driving here 5 years, and somewhere in there I started writing it down instead of just telling it at parties.
For some people, I’m the first real version of Chicago they ever meet. Someone from here, who loves it here. Whatever they’d heard about this city before they got in the car, I’m what they get to hold it up against.
The city was never mine to begin with. I just grew up in it, and I get to hand a piece of it to whoever’s in the back seat. I’m proud to be that. If someone gets out with a kinder picture of Chicago than the one they got in with — and of people anywhere — that’s the whole thing.
5 Star Confessions is the first book. It won’t be the last.
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