DoorDash and Postmates Padded My Pockets — and Taught Me a Life Lesson

Extra money is great, but so is responsibility

Photo: Clay Banks/Unsplash

I won’t lie to you: delivering for DoorDash and Postmates over the past few months has been very good business. Thanks to the extra income, I paid off $1,000 of debt, saved up $2,000, and only had to sacrifice my weekends. I still dedicate my weekdays to writing, but Saturday and Sunday are for dashing (as we call it).

All was going well — until I started to bite off more than I could chew.

When I started reading up on food delivery services, I learned that drivers could make serious bank if kept two or three apps running simultaneously. Pick up one order from McDonald’s for DoorDash, swing over to the P.F. Chang’s for Postmates, and if you’ve got dreams of going pro, squeeze Wendy’s in for Grubhub and the trifecta. If you’ve ordered food and watched your driver deviate from the map and end up in the next state over, this strategy is likely why. (Or, like me, they could have a half-broken GPS.)

I felt like the Mad Hatter, driving from restaurant to restaurant with enough food in my car to feed a nation. I pocketed an extra $100 a day, and my delivery days were jammed. No boredom, more money — what’s not to like? Getting screwed, as it turns out.

Being the ambitious type — and the “I want more money” type — I began to increase my workload. No more using one app a day: I wanted to go all in. I felt like the Mad Hatter, driving around my neighborhood from restaurant to restaurant with enough food in my car to feed a nation. I pocketed an extra $100 a day, and my delivery days were jammed. No boredom, more money? What’s not to like?

Getting screwed, as it turns out.

The workload may have been heavier, but it was the logistical quagmire that ended up dragging me down. I’d debate in my head: Should I go pick up Carvel for Postmates first or deliver this pizza for DoorDash? No, no, no, I’ll cancel the ice cream, deliver the pizza, wait for a new Postmates order, and pray to God I’m not insane by morning.

I needed a break. Maybe a straitjacket. But all it took was one very embarrassing episode to resolve the entire situation.

I called in a big pizza order for Postmates, and told the cashier I’d pay when I got there. I was in no rush — pizza takes time — and DoorDash kept spamming me with deliveries like everyone in my city had simultaneously developed a massive case of munchies. So I headed to handle a couple of those in the meantime.

Then, 15 minutes into my delivery shift, my phone chirped out the “game over” tune from Super Mario Bros. — the signal that a Postmates order has canceled. (How the company got the rights to the song is anyone’s guess. If the company got the rights to the song is anyone’s guess.) The customer must have seen I didn’t head directly to their address, and thought I’d abandoned their order.

I wasn’t super thrilled about calling the pizza place to let them know; they’d already spent the time and food to fulfill the order. So, uh, I didn’t. Instead, I decided to avoid the awkward conversation and let the message they’d get from Postmates do my work for me. It wasn’t like the cancellation was my fault. I was just completing another delivery — for a different service — before picking up the order.

Well, that pizza place called me. I was driving, so I let it go to voicemail. (I know, I know.)

Another 20 minutes later, I got another call and decided to pick up this time. I explained what happened to the cashier, and she let out a loud sigh. “Okay,” she said, “please don’t let this happen again, we have to throw this food out now.” I began to apologize, but she hung up before I could finish.

It bugged me — not that she cut me off, but that I screwed up by taking on too much work, and now my character was at stake. Some people might chalk this up as a “whatever, time to get on with my life” kind of moment, but not me. I needed to make this right. The order total had been $31, so I drove to the ATM, then drove like a maniac to the pizza shop with the exact amount in my pocket. After parking the car, I took a deep breath, walked to the front door — and found out they were closed.

So the next day, I drove back to the pizza shop, marched in, and stuffed the cash into the tip jar. Money doesn’t mean anything if you can’t preserve your character. I was in the wrong, and I couldn’t just let it go without making it right. The way I saw it, I could lose $31 or my soul. A bit hyperbolic? Maybe, but you don’t have to believe in karma to know that negative acts will eat away at your conscience.

And next time, I’ll only bite off as much one customer can chew.

Ultramarathoner, Comedian, Crypto Man. Also a diehard Trekkie 🖖🏾| You can catch me on my publication Yard Couch.

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