The first ride was a guy named Derek who got in smelling like a Subway footlong and immediately asked me to turn off the music. I had exactly one song playing — something low, something inoffensive — and Derek needed it gone. I turned it off. Derek did not say thank you. Derek ate whatever was in that bag for the entire eleven-minute ride and got out without a word. I sat in the parking lot of a Walgreens on Atlanta Highway and thought: this is fine, this is going to be fine.

It was not fine. I lasted nine days.

I want to be clear that I went into this with real optimism. I had the app, I had a reasonably clean car, I had a pine-tree air freshener from the gas station and a phone mount I'd ordered off Amazon for eight dollars. I had done the math — loosely, the way you do math when you want the answer to come out a certain way — and I had convinced myself that a few hours on weekend evenings would cover something real. A bill. A cushion. Something.

The Brother-in-Law Planted the Seed, Which Should Have Been a Warning

It started, as several things on this list have started, with my brother-in-law. He had been driving for about three weeks at that point and was in the phase where it's still exciting — before the mileage adds up, before you've had your first truly unpleasant passenger, before you've done the gas math with any honesty. He was enthusiastic in the way that a man is enthusiastic about a thing he has not yet really examined.

"Bro, you just drive. That's it. You just drive and they put money in your account. I cleared like — I don't even know, a lot — last Saturday."

He genuinely didn't know. He had not looked at the actual deposit. This is important context.

I had DoorDash already, which I understood. DoorDash is transactional. You pick up a bag, you drop off a bag, nobody is in your car, nobody asks you to turn off the music. The bag does not have opinions. I told myself rideshare would be the same energy, just with a person instead of a burrito bowl, and that the person would be quiet and grateful and we'd have a pleasant five minutes and I'd get paid.

I downloaded the app on a Thursday night. I was approved over the weekend. Monday I did my first ride. Monday I met Derek.

Nine Days of Strangers Sitting Behind My Head

Here is the thing nobody told me, or maybe they told me and I didn't listen: you cannot see the people behind you. They're just there, in your back seat, in your peripheral vision in the mirror, breathing. Some of them want to talk. Some of them do not want to talk but make noise anyway — sighing, scrolling with the sound on, conducting a speakerphone call about something that is genuinely none of my business. One woman argued with someone for the entire ride from the EastChase area back toward downtown and ended the call right as I pulled up to her building, said "thanks hon" to me like I hadn't just heard all of that, and was gone.

I did about four or five rides a night on the evenings I went out, which was not every evening. I had the kids some nights. I had work that ran late some nights. I had nights where I sat in a parking lot for forty minutes waiting for a ping and just... drove home. Those nights were their own special kind of demoralizing.

Day six was the worst. I got a long ride — which felt like a win — out to a suburb I didn't know well, and then the app routed me back through every construction zone in Montgomery County, and by the time I was home it was close to midnight and I had to be at my desk by eight. I sat in the driveway and did the math for real this time. I wrote the numbers in my phone. They were not good numbers.

Day nine I picked up a college-aged guy who asked me if I'd considered "just doing this full time." I said I had a full-time job. He said, "yeah but like, the freedom though." I said "yeah." I dropped him off. I drove home. I did not open the app again that night.

Fifty-Three Dollars, One Tank of Gas, and a Certain Amount of My Soul

Over nine days I made fifty-three dollars and change before the app took its cut. After the app took its cut it was less. After gas it was less than that. I did not write down the exact final number because I think some part of me didn't want it to exist as a document.

The eight-dollar phone mount is still on my windshield. The pine-tree air freshener lasted about two weeks. Those are sunk costs I'm choosing not to think about too hard.

The real cost was the hours, and the hours had a texture to them that DoorDash hours don't. With DoorDash I'm alone. I'm listening to whatever I want. I'm a little brain-off, a little zoned out, just navigating and handing over a bag. With rideshare I was on the whole time. Presentable. Agreeable. Performing a version of myself that was cheerful at 10:45 on a Tuesday night, which is not a version of myself that exists naturally.

I'm a remote software engineer. I spend most of my day in a state of low-grade social conservation. By evening I have approximately nothing left for strangers. I knew this about myself and I signed up anyway, which is the part where I was visibly wrong and I'm willing to say so.

The App Is Still Installed, Which Tells You Everything

I didn't delete it. I want to be honest about that. It's sitting on my phone right now, somewhere in a folder with a few other apps I opened twice and never closed accounts on. I keep it because — I don't know why I keep it. Optimism, maybe. The same optimism that got me into this.

What actually stuck was a sharper understanding of what I'm willing to trade. DoorDash is still on the rotation because the math is bad but the experience is bearable and I know exactly what I'm getting. Rideshare math was also bad and the experience cost me something I couldn't quantify, which made the whole thing feel like a worse deal even when the dollars were comparable.

I also came away with this: the brother-in-law is still driving, three months later, and he's still in the phase where he doesn't quite look at the deposits. I find this admirable and slightly worrying and I don't say anything because he seems happy and who am I to audit someone else's optimism.

My oldest asked me why I stopped doing "the driving one." I said the hours didn't work out. They accepted this without follow-up questions, which was generous of them.

The app is still there. I'll probably open it again someday — a slow weekend, a weird bill, a moment of misplaced confidence. That's sort of how this goes. Post the Ls too.

Note: Everyday Hustle Jeff is the written side of a digital series. These accounts are composite and dramatized. Any figures are what they were on the day, for one person, and are not a projection, a track record, or advice.