From Hand to Mouth – A “Successful” Artist Hustles, Explores the Other Gig Economy, and the Little White Tesla That May Have Broken His Will

This title is sticking. It was the teaser I shared yesterday. You’ll have to make a few inferences on your own. If that’s not working—ask.

Also, note that there’s absolutely no intention to bellyache or complain, with the exception of the driver of that little white Tesla.

I’ve been exploring DoorDash as a means to bridge cash flow gaps. Work comes when it comes, and no amount of hustling will bring patrons and students to my door.

In short, DoorDash is great at generating immediate cash in limited amounts. (It’s also terrible. That’s the part I’m leaving out for another go at this topic.)

I want you to know a few things about DoorDash—as a consumer:

  • Dashers come from all walks of life. If you’re reading this, you have a good idea about who and what I am. I’m not atypical. I’ve seen grandmothers, housewives, teens, and the sketchy. (There are the sketchy, for sure.)

  • There’s a lot of bait and switch with beginning drivers. You make great money the first week or so. Then… (It’s complicated. It’s real.)

  • The tip you offer when you order isn’t a tip. It’s a bid. DoorDash rarely pays more than $2–$3 for a run. The drivers receive an offer that includes your tip. We don’t know what part of that offer comes from you or DoorDash. In addition to the bid, we see mileage (one way), the restaurant, and the approximate location of the customer.

  • The best offers—a high bid, short route—go to the most aggressive and experienced drivers. It makes sense to tip well at the front end. But remember, that’s not really a tip.

  • Drivers often balance two orders, coming and going to and from two locations. That means one of these meals is sitting in the car longer than you or the driver would like.

  • Drivers are at the mercy of restaurants. We’re summoned to arrive when the meal should be ready. This rarely works out. You’ve been to restaurants and seen us collecting up front, anxiously watching our phones. The restaurants purposely call us in early so that the orders don’t pile up.

  • Waiting for the next run (My 7-minute estimated wait was 35 minutes yesterday. This is typical.)

  • All of our runs are one way. I picked up a recent run that led me to Carmel. The run they assigned to get me home was miles north of Westfield. I once ended up on a 60-minute rush hour run to Broad Ripple for $7.

  • You may refuse any offer, but one of your metrics takes a hit. Best drivers get the good offers. To keep the points, you take a run to Broad Ripple.

  • On a productive shift, about a third of your time is downtime—often burning gas and not getting paid.

  • As a driving gig worker, about a quarter of your pay goes to gasoline and about a quarter to taxes. On a slow night, you may spend significantly more on fuel. Remember that afternoon drive to Broad Ripple? Drivers just eat the wear and tear on their car.

I think you get the idea. It’s so hard not to write more and peel back more layers. Point fingers. Complain. Make it complicated. 

There’s no exposé here. This is what gig work is. Everyone in the network gets it and understands. Unfortunately, many are trapped here—or feel that they are.

I’m not. I’ve been a gig worker—not so much on the underbelly—for decades. I’ve got a dozen gigs and a delicate dance to keep my head above water. Sometimes the next dance on your card is with a partner that doesn’t bathe.

Yesterday, I had an exceptionally difficult morning. When I popped out of bed at 8:00ish, DoorDash notified me that it might be a good time to pick up a shift. My brain—which didn’t get to drink coffee until noon—(is the foreshadowing too obvious?) told me that no one needed anything on a Sunday morning. Unfortunately, I just needed cash. I took it.

The first run came straight away. (Of course, it did; that’s why they called me out.) It was a short run from Burger King to West Maple Avenue for $6—about a mile drive. These runs can be great; if the restaurant has the meals ready, I can deliver and be ready for my next run in 10 minutes.

The second run came right away. It was going to be a good morning! It was a $4 run to Old Town. Not great, but these pile up.

I returned to a Hot Spot. (To get the best work, you park in a designated spot that’s adjacent to the restaurants in demand.) I parked at Steak ’n Shake—Starbucks ready—for 35 minutes. I was about to clock out and head home when another run came in. To Meijer to grocery shop for $7.75.

I almost didn’t take it. Meijer on a Sunday morning is an event in itself. Long lines of folks that only have time to shop on weekends. The list was simple—some produce items, greens, an onion, and sweet potatoes. That was simple. The woman also wanted a container of unsalted chicken broth. Should be easy. I found it quickly, scanned it, and DoorDash refused it, telling me it was not the right item. I was confident that it was. I texted the customer and confirmed. After about a dozen prompts (hyperbole?), I was able to override the system and add it to my cart.

Great! Not so bad. I headed for the self-checkouts. Short lines. Fast. When I began the checkout, I was prompted that I was not to use the self-checkout. With a sigh, I reloaded my cart and pushed—against the line—back out to the checkouts. Only two lines were open, and the carts were stacked high. There was a problem with someone ahead of me that required at least two supervisors’ attention. At this point, I knew I’d be late, my score cut, and possibly have an upset customer. I texted her to let her know what was going on and waited.

Another anxious moment for Dashers is the checkout at stores. We all have a debit card that belongs to DoorDash. As we check out—in real-time—they load the card to cover the costs. That way, if I’ve made an approved substitution or couldn’t find something, I don’t have to deal with it.

In the three weeks I’ve dashed, I’ve only received two real tips—after the delivery. There is absolutely no incentive for anyone to tip. In a sense, they already have. Most don’t even see the driver to see how they handle the food or to hand off cash. I never expect, or even hope for, them. I had done my job for an agreed-upon price. $7.75. High anxiety. 45 minutes. 14 miles. Ugh.

This is when I began writing this essay in my head.

Then I took a $5 run—6 miles—to deliver Starbucks.

This was my easiest pickup EVER. The bag was packed—neat and tight and on the counter—when I walked in. Two small coffees in a bag. Coffees in a bag? I decided that Starbucks knew what they were doing and turned north on S.R. 37, wondering why it made any kind of sense to drive two cups of coffee 6 miles for any reason. The carbon footprint. Who’s this lazy? (Sorry. I am judging.)

Back to turning north on S.R. 37. Leaving the light and making the turn… mid-turn… the little white Tesla ahead of me momentarily slams on its brakes—so do I—darts around the car ahead of it, and accelerates, weaving in and out of traffic.

I look down, and my car floor is a soup of wet bag, inadequate drink holder, and two small Starbucks cups.

I was beyond my breaking point. I’m proud to say I held it together, but I was gutted. Just gutted.

I pulled into a parking lot and contacted DoorDash. They refunded the customer, paid me half my offer for my trouble, and didn’t penalize me. That was gracious.

At the end of the day, I had driven about 20 miles and made $17.50.

Will I Dash again? Sure thing. I need a side hustle for my side hustles.

However, last night I explored a more structured, go-to-work side hustle. We’ll see where that goes. 

(Note- If you’re worried about our income, don’t. The essentials are under control. This strain is the result of planned projects being delayed and learning a bit about selling writing. The money comes at publication, not acceptance. That money I thought was coming March 1 is really June 1.)