Careers and Side Hustles in Creative Work

By Jonathan Wynn

In an article titled “Institutional Office and the Person” one of the great mid-century sociologists, Everett C. Hughes, wrote that a career is “the moving perspective in which the person sees his life as a whole and interprets the meaning of his various attributes, actions, and things which happen to him” and that any self-appraisal was dependent on how that person moves through an organization, as a kind of sequence of roles. What if we don’t really work in institutions anymore?

Careers, particularly in the creative world, don’t match Hughes’ model. People are not moving through any one organization, or even any one career, but several and, at times, concurrently. When you graduate you might not have one career, but two or three. (It is likely, in fact, that the average graduate will have three or four career changes, and four job changes by age 32.) Millennial workers will likely have to work more than one job to make ends meet. You will, quite possibly, have to make ends meet with what are called “boundaryless” jobs and careers.

Boundaryless careers sound somewhat attractive, particularly in the creative world: flexible hours, flat or vague hierarchies, some autonomy wherein one can cobble together work that is free of more formal labor conditions but with a fair amount of growth in income. In an article called “Predictors of Success in the Era of Boundaryless Careers” Eby, Butts, and Lockwood note that these careers “transcend organizational memberships and consist of sequences of experiences across both organizations and jobs.”

Somewhere in the enthusiasm for “boundaryless careers” and the new “gig” economy of Uber and AirBnb is the fact that these jobs are unlikely to turn into a full-time job, or be particularly fulfilling. The popular press is catching on with this realization, publishing reports like “Let’s Call Millennial Side Hustles What They Really are—Part Time Jobs We Need to Survive,” and “The Necessity of the Side Hustle.” And I bet Hughes would enjoy writing about this phenomenon.

In the U.S.’s new consumption-based service economy, there a certain subset of folks who are drawn to jobs that are more creative in nature. Although, to be sure, tech jobs are only now catching up to the working conditions that creative types have always experienced. In a book that elegantly tracks the life course of a novel from its inception through production to its reception by a reading public, Clayton Childress’ Under the Cover cites the experience of midcentury novelist Malcolm Cowley, who notes that authors live “on crumbs from a dozen different tables.”

The stories of working gigs that can pay the bills yet are only minimally distracting main career-goals reminds me of people in the fine arts working in cafes and bars that allow for irregular hours and still some income. Richard Lloyd’s Neo-Bohemia is a study of how all these creative and side hustle jobs coalesce into a kind of subcultural ecosystem.

I lived in one of these side hustle communities back in graduate school and, even though graduate school isn’t always a creative endeavor (although I’d disagree), it was truly exciting to be around people who were all doing creative work. While working in a Brooklyn café to pay the bills while I was in grad school, we all supported each other in our “real” jobs: going to performances, gallery openings, even dissertation defenses.

Michael P. Jeffries’ Behind the Laughs: Community and Inequality in Comedy illustrates that fusion of personal and professional lives in Los Angeles’ sketch comedy, improv, standup and screenwriting worlds. Aspiring comedians, like those I lived with in Brooklyn, require amounts of reciprocity and respect from their social network, which works as a kind of a family. (Families, Naomi Gerstel corrected me once, are not generalizable as positive, of course.) Similarly, Jooyoung Lee mentions how an open mic community can serve as a kind of family in his book, Blowin’ Up: Rap Dreams in South Central.

Jeffries gives us a sense of the experiences of being on the edge of potential success and failure among folks who do creative work but need the side hustle too. Comedy gigs are uneven, rare, and uncertain, making success anything but guaranteed. Comedians work hard out of necessity, requiring versatility in working in many different entertainment spheres.

What happens, then, when creative dreams go unfulfilled? Ofer Sharone, whose book Flawed System/Flawed Self examines how wider employment systems shape whether or not someone who is unemployed will center blame on themselves, or the wider market. Sharone sees Americans as more inclined to blame themselves, but contrary to that finding, Jeffries sees U.S. comedians as having a greater sense of self-authorship. In line with the ethos of the new gig economy, a successful career for Jeffries, a comic defines success for themselves knowing that comedy isn’t meritocratic, and whether they have had public experiences they characterize as successful.

On a more positive note, I’ll end with a story of how side hustles were actually institutionalized. At one time, Google saw them as an important enough part of the creative tech economy. So important that they actually paid their employees to spend 20% of their time to be on creating and developing new products. That policy ended officially in 2013, but it lives on in other ways. (Here’s a nice write up of how tech companies can’t really kill 20% time policies.)

Let’s think, instead, about how these creative jobs and side hustles can have a symbiotic relationship. Do the skills of the comedians in Jeffries’ book and the MCs in Lee’s book develop in their entertainment scenes transfer to other jobs? Lee, for example, notes that the MC skills of one of his respondents, Flawliss, were perfectly suited toward sales: grabbing people’s attention, keeping it with some humor and entertainment, ad libbing on the fly, and so on.

In both books these creative types learned how to craft an identity that can be a brand, and learn that performances need to be transformed into products transforming a subcultural career into a cultural career. It’s like Google’s 20% time, in a way. Granted, they want to be professional comedians and hip hop stars. But in both books there are moments wherein we learn that some skills are transferable to other kinds of jobs, and other kinds of side hustles. These moments remind me of a great move in a book by Sudhir Venkatesh, wherein he showed that running a drug ring was just like running a formal business. It’s a nice move that normalizes what everyday folks might think of as abnormal or irrational behaviors, whether it is being in a gang, or irrationally chasing improbable dreams.

For more on the lives of creative workers, there is a lot of research reports and data available on the Strategic National Arts Alumni Project (a name that was transparently generated for the purposes of having a great acronym: SNAAP) website.