This is what happens when a Gig Economy devotee goes full time

When the poster child for Generation Flux gets a full-time job, he realizes that maybe stability isn’t the enemy.

This is what happens when a Gig Economy devotee goes full time
[Illustration: Kirsten Ulve]

“What do you do?” It’s a loaded question even in the best of circumstances. But when your career is a crazy quilt of activities that feed different aspects of your personality—in my case, stand-up, punditizing on news shows, writing, delivering speeches, and heading a fledgling company—the only way to answer is with a comma-separated list of titles. Meanwhile, inside my head, I am giving my interlocutor the heavy side-eye for trying to reduce me to just one thing.

A few years ago, I celebrated my mobility, flexibility, and refusal to be defined in this very magazine, proudly stating, “Uncertainty is the certainty. Change is the constant. Experimentation is rewarded. Stability is an impediment.” Then, to be even more clear, I added, “If I could get a big check from TV, that would be cool. But I’m not desperate for those things.” By “those things,” I meant that one thing would answer the question of what I do in less than a tweet.

Then last fall, I got offered a job cohosting a TV show. Faced with a real-life choice between the gig economy and routine, I hesitated. The TV network, Pivot, was new and unproven. The city, Los Angeles, was not New York. The universe was testing my instability theory.

The more I considered it, though, the more I warmed to the idea of losing my geospatial flexibility. Airports didn’t have to be my second home. I could have a daily rhythm, swipe in at a security desk every day, make small talk with the same people, and be able to predict my whereabouts beyond the next 48 hours.

On October 6, 2014, I joined Jacob Soboroff and Meghan McCain as a cohost of TakePart Live, a nightly issues-oriented news-talk show. It was weird having the same schedule every day (right down to eating my post-show Sun Chips and banana), but the work was fun and the intellectual range intense. I’d learn about the plight of Ugandan refugees and then explore the racial and gender politics within the latest TV shows. The format and rules of television at that pace were foreign to me, but I felt I was adapting to it all. Then, just nine weeks into my grand experiment with steady employment, our team found out that the network would not renew the show for 2015. “But I just learned the TV format and how to get my makeup off in less than five minutes!” protested my inner voice, adding in a forceful whisper, “And in New York, winter is coming!”

In six months I had gone from not wanting something, to wanting it, to getting it, to losing it. Rather than go home to New York (again, winter), I explored L.A. and used my newly found time to think. For years I had preached the gospel of inevitable, persistent change and the death of security because of technological disruption. In celebrating the relentless onslaught of the future, I had undervalued the present and the benefits of developing a regimen and honing a craft day in and day out.

My short-lived stint with a regular gig (forget that life on TV isn’t exactly “regular”) showed me what my life might look like with a little more certainty and enhanced my respect for predictability. I’ll always embrace change—since these personal epiphanies, I’ve started a podcast and gotten very active on Snapchat (check me out at snapatunde)—but the experience of getting and losing that big job has given me valuable information that’s helping to craft the next one.