How Many Gigs Does It Take to Make It in NYC?

Longreads

The gig economy (“a phrase which encompasses both the related collaborative economy and sharing economy”) is inescapable. AirBNB (now in Cuba) and Uber flood your feeds regularly. Chipotle recently announced its partnership with delivery startup Postmates—burritos at your doorstep are imminent (Quality? Price? Questionable). These companies seem successful, but what about the individuals who carry out their mission statements—the couriers, the hosts, the drivers? Is there genuine money to be made in the gig economy? Is it an economically—and emotionally—viable means of support? For one month, Sarah Kessler attempted to employ herself using TaskRabbit, Fiverr, Skillshare and other “sharing”-centric companies. It didn’t go well.

When I come across the task, “Proposal Flash Mob in Central Park,” I know immediately that I am exactly the wrong person for the job. The training video opens in a mirrored dance studio, with a man in a tight-fitting black t-shirt. “Please make sure you…

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