I got into freelancing through comedy.
Once upon a time, back when Facebook’s data breaches were still a secret and Elizabeth Holmes walked through the Palo Alto Whole Foods with her head held high, I was one of those mythical tech workers—a data scientist at a San Francisco startup. During a lull in my job (startups are chaotic, although if you’re at a low enough level, you can last a while without anyone realizing you’re not working), I began doing stand-up comedy at night. After a year of 20-hour days balancing both, I had saved up enough money to quit my tech job and give myself time to “regroup,” as I told my mother, or, more accurately, catch up on sleep.
I intended to go back to work as a data scientist, but I wanted to continue my stand-up career, and I couldn’t find a job flexible enough to do that. I know there are full-time jobs that don’t require a full-time effort, but—as I quickly learned—they rarely advertise as such. I loved comedy, and I was nervous about committing to anything that might take time away from my craft.
Instead, I picked up any work I could find—I walked dogs, tutored for the SATs, wrote social media posts, blogged. For a while, I had a job writing inspirational posts on LinkedIn. I’d roll out of bed at 10 a.m., hungover and still caked in the black mascara I’d worn to my stand-up show the night before, chug black coffee and belt out, “12 Things the Most Successful People in the World Do Before 8 a.m.” I felt alive.
There was limited risk at the time. I was still on my parents’ health insurance when I began freelancing, and I was still in the age range when all my friends routinely discussed going back to grad school. To be fair, they still do, but it’s more along the lines of, “If X career doesn’t pan out, I’ll have to go back to grad school.” It seemed okay that I didn’t have a full-time job, but it also seemed transitory.
At the time, I wouldn’t have said that I wanted to be a writer—I would have said I wanted to be a comedian. However, the only paid comedy gigs I got were as a writer. I started writing for the New Yorker Shouts & Murmurs column, which led to a book deal, which provided me with justjust enough financial security to not look for a full-time job for a few months, even as my tech savings ran out. When the book was finished, I needed something new, but the idea of going back into an office every day was wholly unappealing.
I kept finding more and more freelance opportunities. I somehow thought writing comedic essays might lead to a NetflixNFLX stand-up special, but lo and behold, they steered me toward writing non-comedic essays. Or tweets for random small businesses who wanted to hire me for exactly six days. At some point, I began dividing my time into work on my “true craft” (stand up comedy, TV pilots no one would ever read), and “money” (freelance writing and social media jobs). I still didn’t see myself as committed to any one career—and that’s part of the benefit of freelancing. You never have to fully commit.
I didn’t consider myself a freelancer until I filed taxes in 2018. I’d been paid by about 30 entities in 2017, and I had a vague sense that things were about to get complicated. At the start of 2018, as the 1099s rolled in like old lovers back for one last hurrah, I had a profound thought: If I tell TurboTax I’m a freelancer, will my overall tax bill be lower? I still have no idea—I’ve only tried it one way. But that year, I became one of the 36% of Americans who identifies as a freelancer.
I wasn’t making so much money that I had the capacity to hire anyone else, which meant I managed all my own financials. As a freelancer, I learned far more about accounting than I ever intended (or cared) to. But I also learned how to manage my own schedule, seek out new clients, gauge how long a specific project will take, and plan out how much vacation I wanted. I became a one-woman end-to-end operation, managing all the details I’d once thought were the exclusive purview of HR professionals. It didn’t happen all at once. In fact, almost all of it happened through trial and error. I went a full year without taking a single day off before I realized I needed to plan and save for vacation in advance if I didn’t want to lose my mind—but more on that later.
I was long hesitant to call myself a “full-time freelancer,” in part because I worked far more than 40 hours a week. But after six years at it, I have to accept that I’m one of the 14% of Americans who freelances full-time (two-thirds of whom are under 35). what I am. In recent years, I’ve been offered salaried positions, and I know I’m not alone in considering this—49% of freelancers say they would go back to a traditional job. And while the appeal of health insurance has almost won me over, something has always stopped me. At the end of the day, the benefits of freelancing have outweighed the costs.
In this column, I’ll dive into what it’s like to be a freelancer: tips for those already part of the hustle, advice for those considering taking the plunge, and general thoughts about the freelance/full-time divide. It’s certainly not all rosy, and some days I think to myself, “Gee, I wish I made more than $450 dollars this month.” But it’s the deal I’ve made myself, and for now, I’ll take it.
