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 are familiar with this choreography before you commit to that rehearsal so we don’t have to waste any time,” he explains in a high-pitched voice before counting out about three minutes of what looks to me like complex choreography. During slow claps at baseball games, I’m the fan who claps on the wrong beat. A real rabbit might have a better chance of learning this dance.

But the job pays $20, and because it involves a two-hour rehearsal beginning at 8 a.m., it could help me finally achieve an elusive goal I had been working toward for weeks: a full day of micro-entrepreneurship employment. I had already lined up a personal assistant gig for mid-afternoon, and I had bids out on a handful of odd jobs in the evening. Experience has taught me not to count on any of these, but still, here was the morning timeslot that could lead me to an eight-hour workday. I accept the offer.

And then I immediately panic.

Read the story