The DoorDash Shift I Forgot to Count the Parking

It was a Tuesday night, maybe seven-thirty, and I had a two-hour window before the kids needed anything from me. The app was surging — slightly, not dramatically, the kind of surge that looks good on a phone screen and means basically nothing once you're in traffic. I accepted it anyway because the alternative was sitting on the couch watching something I'd already seen.

Downtown Montgomery on a weeknight has its rhythms. The restaurant cluster around Dexter Avenue gets busy, the orders stack up, and if you're lucky you can run three drops in the same half-mile without burning much gas. I knew this. I had done this before. What I had apparently decided to forget, completely and without any good reason, was that every single parking spot in that corridor costs money after five p.m., and I did not have my quarters-in-the-glovebox system anymore because I'd spent them on a car wash two weeks prior.

So I paid for parking. Four times. On a two-hour shift. With my debit card, like a person who does not understand his own situation.

Why I Keep Driving Downtown Even Though Downtown Costs Money to Stand In

The honest answer is that downtown orders pay better on paper. The restaurants are closer together, the drop-offs are denser, and for about forty-five minutes on a good night it actually feels like the math is working. I've had shifts down there where I ran four orders in an hour and felt genuinely clever about it.

The problem is I keep doing the math in my head during the good part and stopping before I get to the parking receipts. It's a habit I've documented before — the math I do after the shift is always less flattering than the math I do during it. I know this. I keep doing it anyway. This is either optimism or a learning disability and I genuinely cannot tell which.

The brother-in-law had actually warned me about this specific thing the last time he was over. Not about parking specifically, but about hidden costs in general. He was pitching me on a vending machine route at the time, so I wasn't listening as hard as I should have been, but the principle was sound.

The Four Parking Meters That Quietly Ate My Tip Money

First stop was a pickup on Commerce Street. Pulled up, found a metered spot, tapped my card because the meter only takes cards now, and paid for thirty minutes I didn't need. The pickup took four minutes. I left twenty-six minutes on the meter for the next person, which felt generous and was actually just wasteful.

Second stop was on Coosa. Different meter, same card tap, same four-minute pickup. I was starting to feel it but I told myself I'd make it back on the tips. The tip on that order was two dollars and forty cents. The meter was a dollar seventy-five. I was technically ahead by sixty-five cents on that transaction if you don't count gas or the first meter, which I was actively choosing not to count.

By the third stop I had found a loading zone that I was about sixty percent sure I was allowed to use. I was not allowed to use it. I did not get a ticket, which felt like a win, and which I now recognize was just luck that I am absolutely going to spend again sometime.

The fourth stop was back near Dexter and I just paid the meter again. A dollar fifty. At this point I was running on the logic that I was already committed to the shift and stopping to recalculate felt like quitting. That is not good logic. I know that. I was tired.

"Dad, did you make money tonight?" my oldest asked when I got home. I said yes. I said it with confidence. I had not yet done the actual math.

I did the math later. At the kitchen table, after the kids were in bed, with the receipts from my pocket laid out next to my phone. It looked like a crime scene for small amounts of money.

Thirty-One Dollars and Eleven Cents, Before I Found the Fourth Receipt

The shift ran about two hours and fifteen minutes door to door. The app showed earnings that looked reasonable until I subtracted things.

• Gas: I don't track this precisely enough, which is its own problem, but the route I drove was about nineteen miles of actual movement plus circling. Call it four dollars, conservatively.
• Parking: six dollars and twenty-five cents across four meters. I found the fourth receipt in my jacket pocket the next morning. It was a dollar seventy-five that I had completely blocked out.
• Net, after gas and parking: thirty-one dollars and eleven cents for two hours and change.

Fourteen dollars an hour, roughly, before you account for wear on the car, which I don't know how to calculate and have been told I should learn. Victor mentioned once that most people dramatically undercount vehicle depreciation on gig work. He said it the way he says most things — not as a lecture, just as a fact he happened to have. I nodded and then continued to not calculate it, which is where I still am.

The shift I'd planned around a promo code paid better per hour than this one did, and that one felt like a loss at the time. That's the part that really got me when I sat with it.

What I Changed, Which Is Not Much, and What I Wrote on the Whiteboard

I put "PARKING" on my whiteboard. In caps. Next to the other things I keep forgetting to factor. The whiteboard has a lot of words on it at this point and very few of them have been crossed off, but the act of writing something down makes me feel briefly organized, so I keep doing it.

I also moved my DoorDash downtown window. If I'm going to run that corridor, I start before five when the meters are free, or I stay on the east side where the parking situation is less hostile. That's not a strategy, it's just me adjusting after the fact, which is how most of my adjustments happen.

The thing I didn't change is that I'm still doing the downtown shifts. The density is real even if the parking eats into it. There was a whole week where I tried to actually make the numbers work in a systematic way, and what I learned is that the numbers don't really cooperate with systems — they just do what they do and you adapt or you don't.

I also put a roll of quarters in the glove compartment. Three days later my youngest found them and asked if we could do laundry. We did laundry. The quarters are gone.

The app is still installed. I'll probably drive downtown again this week if the surge looks decent enough around seven. I'll probably forget something else. There's a good chance it's the quarters.

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.