In the face of dire job prospects, freelancing felt like it might be a solution; a way to be a writer on my own terms.
The summer I started freelancing, I also worked as a barista at a bicycle store—an odd combined business that served those willing to spend six dollars on a latte and much more on a folding bike. I spent my days steaming milk and directing people towards racks of colorful bicycles, my evenings and weekends writing articles and trying desperately to get them published.
It was 2019. I was twenty-one years old, an undergraduate student in an English and writing program. I was about to enter the last year of my degree and still wasn’t sure what I wanted to do afterwards. At that point, I wasn’t sure what being a writer would even look like.
I had vague fantasies I’m sure many aspiring writers share, ones formed by watching too many rom-coms and speaking to too few actual working writers. Some days, I imagined myself working in a newsroom or at a magazine, clocking in every day to work for some hip, well-dressed editor. On others, I pictured myself writing from home, my days revolving around a beautiful desk in a book-filled office: I might get up, make myself a coffee, and spend the rest of my workday writing a novel or an essay or whatever else.
Though I nurtured these fantasies, I understood they weren’t easily achievable; that stable, full-time writing jobs were few and far between, as people constantly reminded me. Wide-eyed and concerned, the adults in my life would ask questions like “And what do you want to do with that degree?” Or, better yet, the concise and scathing “So, what next?”
I also knew that things in the industry were only getting worse. It seemed like every few months, another media company or literary magazine fired most of its masthead or folded entirely. My career as a writer had barely started, and it was already marred by uncertainty and dread. As I sent out those early pitches, the future was something I tried not to think too hard about.
All I knew for sure was that, slowly, I was getting somewhere. After months of canned rejections or silence from editors, a few essays and articles were getting commissioned. And while these moments seem small in retrospect—little pieces for little pay—at the time, those first acceptances felt monumental.
After the thrill of those early acceptances came frustration.
In the face of dire job prospects, freelancing felt like it might be a solution: a way to be a full-time writer on my own terms. I was following successful, full-time freelancers on Twitter and imagined a life like theirs, not realizing how much work went into the glossy features and culture writing they shared online. I imagined that, come the following summer when I graduated, I might not need to work in customer service at all—that I might be able to be a writer in the way I’d always dreamed, devoting most of my time to assignments like theirs.
But after the thrill of those early acceptances came frustration. I handed in drafts and received silence from editors. It took months for the pieces to get published; months longer for me to get paid. While I worked the espresso bar, I felt distracted and anxious because of freelance projects that felt beyond my control. Still, I told myself the frustration was temporary. I brushed it off as a symptom of just getting started.
I imagined freelancing would get easier. That, as I collected more bylines, I would start receiving as many acceptances as rejections. That, as I gained experience and started getting taken more seriously by editors, navigating the industry might come naturally: pay might get better; pay might come sooner; my work might revolve less around following up and more around writing.
I was mostly wrong.
*
After graduating, I threw myself straight into an MFA program, too scared to leave the comforts of academia and fully enter the workforce. I’m now in my second year, still freelancing on the side. And while I thought more time in school might make me feel surer of myself and my future in the industry, it’s had the opposite effect. My uncertainty has been exacerbated by a fast-approaching second graduation date and the realities of the pandemic, which has shed light on even more problems in the writing industry.
Over the past year and a half, people in various fields have grown increasingly disillusioned with their jobs. This is understandable: the pandemic has highlighted so many of the unfair and unkind ways that companies treat their employees. When the world is falling apart, it’s harder to put up with how much is expected of us at work and how little care we receive in return. Suddenly, a long commute, a lack of sick days or a forced return to the office—things we might have just groaned at before—feel egregious. Even the fundamentals of work life, like living in dense and expensive urban centers, feel frustrating and unnecessary.
This frustration has, in some cases, made it easier to romanticize freelancing. That logic goes like this: if companies are the source of your problems, removing them from the equation solves them. Hate working for a corporation that doesn’t care about you? Work for yourself! Not able to find a good job in your field? Make your own! Scared of being laid off? Become your own boss!
It’s easy to believe that freelancing might be a solution. In the case of writers, journalists and editors, it also feels like an answer to the instability of our industry, where mastheads are constantly shrinking and publications are constantly folding. It might even seem like an attractive option, marked by freedom you don’t get when you’re staffed: you choose your hours, your own projects, the people and publications you work with.
Tim Herrera, who formerly edited the New York Times Smarter Living section and runs the popular Freelancing with Tim newsletter and events, has become a vocal advocate of self-employment on Twitter. Since announcing that he quit his job because of burnout back in August, Herrera has often encouraged others to do the same.
“Quit your fucking job and work for yourself :)” he says in one tweet. This same message—quit your job—appears over and over, even in response to job postings. When someone asked about paying bills, he replied: “Meh these things work themselves out!”
There’s nothing inherently wrong with this advice (though, at a time when work is hard to come by, treating quitting as a one-size-fits-all solution has understandably led to some pushback in the replies). Burnout from work is real, and for him—someone with a padded resume in the writing industry, who admits to having a year’s worth of living expenses saved up—freelancing likely is the best option. To be clear: there are lots of folks who are able to be full-time freelance writers and enjoy it. These can be people who’ve started freelancing while already financially stable; people who take on a wide mix of work they enjoy and that can sustain them; even just people who are just well-cut out for it, thriving on the stress of multiple deadlines and a rotating cast of editors.
But the reality, as I learned firsthand, is much more complex.
Freelancing full-time simply isn’t for everyone. I’ve loved so many parts of freelancing during the two years I’ve done it. There are projects I’m proud of, editors I’m overjoyed to have worked with. But for every high, there’s a grim low point: a month where I’ve anxiously been waiting for payments on multiple projects; a day where I’ve had to suggest a kill fee on a project I loved writing because an editor showed no interest in actually publishing it. The stress of waiting for these things, and having no control over the timing, can feel insurmountable—and I can’t even imagine having it as my sole source of income.
Working for yourself isn’t a solution to the stress and burnout that accompanies work because it’s still working. And while you have the freedom of choosing your own projects and hours, you don’t have a salary, benefits, or even a guarantee that you’ll get paid on time.
When you’re not on the masthead, it can be easy for editors to put your work on the backburner. So much of my career has felt like a waiting game. I wait to hear back about a pitch; I follow up and wait some more; I wait for edits; for publication; for payment. I repeat my questions and feel unheard. There have been times when a piece comes out months after it was first pitched, making the work feel outdated and futile by the time it comes out.
Beyond the waiting, there’s also the problem of work-life balance. The boundaries between what is and isn’t work bleed together when you never clock in or out, email notifications popping up at dinner or on the weekends. And, if freelancing is your main source of income, it’s hard to put your foot down with a pushy editor who demands too much of your time—especially when you’re getting started.
You’re also relatively unprotected: There are no straightforward policies against mistreatment; no ways to clock out; no HR department you can complain to. Even as I’ve gotten more comfortable negotiating contracts and asking about pay, it still feels like walking on eggshells—as though a wrong move could jeopardize future opportunities.
Freelancing can’t be a remedy to the problems of working in the writing industry.
It’s not all glamorous work in the way I thought it’d be, either. So much of freelancing is balancing writing you’re proud of with writing that pays—many of the freelancers I know also do public relations work or SEO, though from the outside it looks like their full-time work solely involves fun, glitzy journalism or literary projects.
Put simply, freelancing can’t be a remedy to the problems of working in the writing industry. You’re still subject to the same editors and newsrooms and poorly-funded magazines as your staffed peers—you’re just working for them without a salary or security.
Part of the problem is that my idea of what being a writer meant was outdated from the start. I was still clinging to my fantasies of the capital-W Writer: someone who clocks in at a publication or who works from home, rising to make coffee and go to their desk, where their day’s work awaits them.
I’m not saying these people don’t exist. (In fact, I’m fairly certain I’ve just described Stephen King.) What I am saying, though, is that this model is unattainable for most writers. There are the exceptions—those who can manage the stress of freelancing full-time, or who defy all odds and rise to incredible levels of success at staffed publications. But for the rest of us, it’s worth remembering there are other options.
That first year of freelancing, I didn’t feel like a “real writer” because I thought a writer had to be fully devoted; that a writer couldn’t also be a barista, or an office clerk, or whatever else. What I’m slowly coming to terms with is the fact that, for me, full-time freelancing just isn’t worth it—and that’s not on me, but on an industry that makes it hard for individuals to succeed.
I don’t know what the years after school will look like for me. After graduating, I might be one of the very lucky people who get a staff position somewhere, my name up on a masthead. I probably won’t be. And, if I’m not, a job with a stable income that allows me to afford rent and litter for my cat sounds like a dream—writing on the side can be enough.
Gabrielle Drolet is a freelance writer and cartoonist based in Toronto.
