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A Little Voyeurism, a Lot of Adventure — My Side Gig Is Kind of Addictive

My DoorDash job takes me places I’ve never been before — and I’m loving the thrill


spinner image Robin Flanigan, of Irondequoit, NY, during her DoorDash shift, Saturday, September 7, 2024.
Robin Flanigan, who lives in Irondequoit, New York, just outside of Rochester, sees her DoorDash job as an adventure. She never knows where she’s going next or who she will meet.
Matt Burkhartt

What do you do as an empty nester in your mid-50s? If you’re like me, you take to the streets. 

If your mind is in the gutter, not that kind of work. I’m talking about driving for DoorDash.

I got the idea after visiting a friend whose 20-year-old son was on his way out the door for a shift with the food-delivery service to earn going-out money.

I thought, Hey, I’m living on a one-person income. I could use a few extra bucks to go out.

But was I too old? I certainly wasn’t in the majority: 51 percent of “Dashers” are between 20 and 30 years old, with only 10 percent over 40, according to job search site Zippia.

My mother hated the idea, my daughter warned me against sexual predators, and I keep it a secret from a close friend because I don’t want any more judgment.

spinner image Robin Flanigan at a restaurant picking up a delivery order
Matt Burkhartt

But I’ve been an entrepreneur since I can remember — collecting cans to turn back to the store for cash, writing books — and sometimes that means forging ahead into the unknown.

Plus, Dashing is exciting. I feel like I’m in a video game — somebody else has the controls and, for the most part, is responsible for where I go. I never know what’s coming next, and there’s a thrill in that.

I don’t have an addictive personality, yet Dashing feels addictive. It’s a common scenario that when my shift ends and I have the option to press the “Dash Now” button again, I have a conversation with myself about why it’s good to stop and go back home. Or I finish with work on a gorgeous Tuesday afternoon an hour before meeting up with a friend to go swimming and think, I could get in a 45-minute Dash.

I’ve also seen parts of my city — Rochester, New York — I never knew existed: cute neighborhoods from the 1950s filled with mid-century modern homes, a Chinese restaurant where servers and patrons were only speaking in Chinese (I’m definitely going back there to eat).

And it’s voyeurism at its most appropriate. I come, invited, to see a snippet of a person’s life, like the skinny 20-something woman who ordered the bottle of Jose Cuervo and the young mother who ordered organic snacks.

I’ve learned not to make assumptions. Such as, there’s no logic to tipping.

spinner image Robin Flanigan dropping off a delivery at a person's front door
Matt Burkhartt

I got stiffed by someone in an affluent suburb, only to have a woman in a lower-income part of the city tip me in cash — not online like most, because she worried DoorDash might not pass along her $3 gratuity to me — and then with hands clasped and torso bowed, say, “Peace, love, light.”

There is a great deal of logic in scheduling, however. I make as much on one Saturday night as I do over four weeknights.

spinner image Robin Flanigan using GPS on her phone to locate a person's home
Matt Burkhartt

I’m lucky. Dashing, for me, is not really about the money. I drive in silence, using the time as a break from the world, even in the midst of the controlled chaos of each delivery cycle. The sights and sounds I wouldn’t have seen and heard otherwise have been rewarding. Standout moments within three days of each other included a plane taking off against the setting sun, a rainbow after a short storm and a flock of geese flying low overhead. You can’t put a price on any of that.

And I’m helping people with my free time. So when my friend texts to cancel our swimming date because of an upset stomach, I don’t consider my night ruined. I head to my newest app instead and find my next adventure.

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