A Year of Freelance Writing Taught Me Why I’ve Struggled With Other Jobs

Jan 4 · 7 min read
[A close-up of two white hands typing on a laptop] Photo by Luke Lung on Unsplash]

Ingrained warnings

You can probably picture the scene: a writer sits in front of a computer, typewriter, or piece of blank paper and wills their brain to function. Writing is so imbued in this mysticism of challenge, frustration, and stubborn endurance that, at least to my younger self, it felt entirely unapproachable. I couldn’t understand why anyone would want to ram their head against a metaphorical wall all day with the risk of making no progress.

As I got older, this repeated characterization of the disastrously-blocked writer teamed up with other warnings about the unbearable solitude of the work and the chaos that emerges when living without externally-imposed structure.

I also picked up on messages that said, unless I was sure my work would immediately gain popular and critical acclaim, I was better of seeking a respectable career in another field. There was always an implied shame about doing creative work without becoming rich or famous, as if being simply decent at one’s job or not appealing to mainstream tastes inherently indicated failure. As someone with a degree and other work options, I understood writing as something that would always remain a secondary pursuit.

But these messages failed to account for the reality that there are swaths of creative people making a career of their work without achieving fame and fortune. And, no one seemed to consider that some of us like solitude and setting our own schedules. Looking back, I can see how I was taught to assume that my career needs are the same as everyone else’s.

The competition: other jobs

To understand why working as a freelance writer has been such a relief for me, I want to explain my experience with other jobs. Since graduating from college, I have worked in two different restaurants, been employed at a handful of schools as an instructional assistant, and completed one quarter of a social work master’s program (yes, for the intents and purposes of this essay, I will count grad school as a job). Each time I changed settings I hoped previous problems would vanish, but they always followed right along.

First and foremost, as a trans person, I have had to deal with misgendering, intrusive comments and questions, and even overt gaslighting and trauma in the workplace. The specific nature of these issues shifted as I proceeded with my physical transition, but they were ever-present — interacting with students, parents, coworkers, customers, instructors, and classmates all had their unique challenges.

Then, there is the general imposition of being around people all day. While I can be friendly, kind, collaborative, and so on, doing so will take a huge toll on my energy, even if I’m only surrounded by people I like. Specifically, as a neurodivergent person, I have to put extra effort into ensuring I communicate clearly through my tone, facial expressions, and word choice. Even when I try my best, though, I am often misunderstood in frustrating ways.

Furthermore, those around me would often casually say things that I found upsetting. For example, spending time in a break room meant overhearing incessant fatphobic and body-shaming comments. Once, a coworker shamed herself for eating the communal snacks, vocally worrying that she would become fatter than her pregnant coworker. At a different job, a teacher would yell at his students, just out of the blue. Many of the kids were scared of him, and this behavior also activated my own trauma, even though I was never the target of his words.

Then, last year, I began my master’s degree with the goal of not only finding suitable and sustainable work but also to connect with more people who shared my values. While I made a few friends, I again experienced the same issues integrating into a group setting. As others bonded over the academic workload or the stress of their practicum placements, I watched from the edge, not really able to relate, and wondering what I was missing. The classes were fine in and of themselves, but when I envisioned a career in the field I realized much of my satisfaction would depend on relationships with my colleagues. The sense of disconnect was one of the main reasons I left the program.

On paper, all of these paths were within my skillset, but none of them proved sustainable. I never lasted more than six months in a single workplace.

Making strengths of weaknesses

There’s a moment near the end of E.J. Koh’s 2020 memoir, The Magical Language of Others, that has stuck with me ever since I read it earlier this year. Koh is just beginning a graduate-level poetry program, and one of her instructors bluntly tells the class that if they have the capacity to do anything else for work, they won’t make it as a poet.

The point is there are so many more accessible, straightforward, and/or sustainable careers than writing (especially poetry, in the example). If one of those feels attainable, you should latch onto it and go.

I think back to this moment when I talk to people about my writing. I’ll often receive comments about my drive, discipline, or even my bravery. I don’t want to totally discredit my own effort, but, in general, my days spent writing don’t require the inner battle that others presume — at least not to the same extent that showing up to any of my other jobs did.

The day-in-day-out process of writing is a good fit for my predispositions, and I find that it even allows my usual workplace weaknesses to become strengths.

When working with my usual publisher, I have full control of what happens to a piece between the pitching and editing processes. Here on Medium, this freedom goes even further. There’s no micromanaging, no one to get in the way of my stubborn preferences. I also can write at the time of day, and days of the week, of my choosing.

I know people often see freelance work as a way to make their lives more flexible, such that they can work from whatever faraway place they wish to visit. By contrast, I take the opportunity to create a rigid structure in my days. This kind of control provides me a sense of comfort that I haven’t had when working in coworkers’ classrooms, for example. Knowing what to expect from each day, before it happens, goes a long way toward decreasing my anxiety.

This isn’t to say, though, that I don’t sometimes switch up my routine. If some part of the process isn’t going well, I have the ability to make immediate changes without consulting, or even affecting, anyone else. I can be as flexible or as fixed as I choose.

Rethinking how we discuss careers

Because I prefer to create my own schedule and environment, to work (and, often, be) alone, and to stick to one task for long stretches of time, writing is a good fit for me. Unfortunately, when receiving career advice, these predilections were never seriously accounted for. Instead, all attention was focused on channeling those with high GPAs and respectable standardized test scores into four-year colleges, while suggesting community college and/or trade school for everyone else. In the social science realm of college, the school-to-work connection continued to feel equally murky.

While I don’t at all regret earning an undergraduate degree (in large part because I had the privilege of graduating without debt), it’s crucial to note that I have not once worked a job that required said degree. When beginning to contract with my main publisher, they simply provided me with a trial assignment to see if I was capable of completing work that met their standards. At the start of my current project, the editor also requested a résumé and writing samples, but the emphasis was on demonstrating ability rather than any level of formal education.

People have long pointed out the mismatch between the education system and employment opportunities (specifically in the U.S.), and the full extent of the problems created by capitalism and its connected structures is much too large for me to explore here. It is important to note, though, that financial considerations usually override many of the other preferences that I’ve discussed here. If the U.S. had living wages and real financial support from the government, people would be much freer to choose how they spent their time.

In addition, when it comes to social norms, we must stop discussing creative careers, and other atypically-structured work, in such limiting terms. When certain aspects of a job or career — such as lack of social contact or external accountability — are presented as inherent challenges, it limits young people’s understanding of their options.

Continuing to frame careers as we have been means reinforcing normative neurotypical (as well as able-bodied, white, male, etc.) experiences as applicable to everyone. There are many reasons why someone might choose, or even enjoy, dedicating their time to something that doesn’t fulfill expectations of prestige. Each one of us is doing our best to meet our needs, and sometimes that means abandoning a plan and stumbling our way into something more sustainable. For me, that more sustainable thing happens to be writing.


If you learned from and/or enjoyed this essay, and are able to, please consider supporting trans people in need by donating to the Black Trans Travel Fund, an organization that provides Black trans women with “financial and material resources needed to remove barriers to self-determining and accessing safer travel options.”


Written by


white, trans/agender, femme often disguised as masc, NW-based. exploring gender beyond traditional narratives. patreon.com/alixperrywriting

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Written by


white, trans/agender, femme often disguised as masc, NW-based. exploring gender beyond traditional narratives. patreon.com/alixperrywriting

Blank Page

Blank Page is home to stories that help creatives get smarter at writing.

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