Why I Left Freelancing
The be-your-own-boss lifestyle is not for everyone.
In October 2019, I left a well-paid, full-time content marketing job to freelance for a year and a half.
In April 2021, I left freelancing and went back to being a full-time, nine-to-five content marketer.
Over the past year and a half, I’ve cycled through a lot of feelings. A lot of feelings.
Feelings about who I am, the meaning of work, the meaning of life. And that forever-question: how should we be spending the limited time we have on Earth in the best way possible?
I still don’t have the answer to this question, but after my experiment with freelancing, I do know that it’s not for me. At least not right now.
Why I Chose to Freelance in the First Place
In October 2019, I decided to quit my job and freelance.
I made this decision because:
- I was feeling stagnant at my job; and
- I wanted to focus more on developing my writing craft, on my own terms, writing what I want.
The job I had paid well, but the commute took up at least three hours of my day. After work, cooking dinner, eating, and cleaning, I had no more energy left to do any writing of my own.
I also felt a lack of meaning in my job. It was very corporate and profit-driven, so I felt little pride in spending one-third of my waking hours dedicated to something like that.
So, I left. I took up a part-time gig at a grassroots non-profit whose mission aligned with my values. And I used the remaining time to work on my own projects and freelance.
Freelancing: the Pros
Now, freelancing wasn’t a bad experience. I thoroughly enjoyed it and I’m glad I did it. I just decided not to do it forever.
Having complete control over your own hours (other than the few hours I gave my part-time job) was exhilarating. I could wake up at noon, work past midnight, work at a café, or even work naked if I wanted (not that I did; chafing is real).
I was 25/26 years old, and after a lifetime of having to please someone else (teachers, professors, parents, bosses, etc.), having complete control over my own time was like one long exhale.
I must admit: freedom was delicious.
I could also write about anything. No more worrying about search-engine-optimized blog posts or maximizing conversions from carefully worded call-to-action buttons. I could write about things that matter: social justice, mental health, media literacy — these are topics that make my heart sing.
I found Medium and began building a modest following here. I found a community and became friends with amazing folks like Anangsha Alammyan (editor of this pub!), Itxy Lopez, and Dayon Cotton, among others. I found camaraderie with writers from all over the world.
2020 was a horrible year for a lot of people, but I did quite well that year, everything considered. I got published in THIS Magazine, which was a magazine I admired since I was a teenager. I also got personal essay published in my local Pride publication, earned my first long-term freelance client, and published regularly with several Medium pubs.
Most importantly, I made a very personal and committed decision to write and finish my first novel.
So, what went wrong?
Freelancing: the Cons
Freelancing was fun for the most part, but I did struggle with aspects of freelancing. And I had underestimated how much these things would bother me.
My main struggles had to do with productivity and taking responsibility for non-writing-related things.
Productivity
When it comes to productivity, I’m somewhat of a contradiction. Under the right circumstances, I can write insanely quickly. Not to brag (ok, somewhat to brag), but my productivity numbers in my first corporate job out of university were pretty insane. In fact, I’ve never missed a deadline. Ever.
But here’s the caveat: to get into this zone of productivity, I need external pressure.
In university, this was the threat of bad grades. In working adulthood, this was the threat of being fired, the potential to earn more, and the fact that in most jobs, other people’s jobs depend on you being competent at yours.
But no one depended on me while I freelanced. I was my own boss, my own company. If I decided to slack off, no one would write me up.
Of course, I needed to earn money, but I was never super desperate because I had my regular part-time gig. And since I have no dependents and no car, I got away with living cheaply.
So, I found myself lazing around a lot. There were…plenty of naps, plenty of Netflix, plenty of doing, well, nothing. I did a lot of reading, which was nice (thanks New Yorker subscription deal!), but I wasn’t nearly as productive as I would have liked.
People who are self-motivated, entrepreneurial types may tell a different story, but this is mine.
Non-Writing-Related Responsibilities
The other thing that paralyzed me was the responsibility.
When you freelance, you’re responsible for everything — HR, accounting, legal, PR, everything. I had to learn stuff way out of my usual knowledge pool. And I had to make some decisions that, frankly, I wasn’t comfortable making.
To be honest, I’ve never been good with responsibility. I have a type of OCD that makes me feel more stressed about responsibility than a reasonable person should.
So, I do appreciate that I don’t have to worry about certain things now that I work for a company. Someone else worries about the budget; I just worry about writing.
Why I Left Freelancing
I ultimately left freelancing because my regular client decided to hire me full-time.
Taking the job wasn’t a decision I made lightly. At first, I was hesitant about losing my freedom and afraid that I wouldn’t have enough time or energy to write.
But this job is admittedly a little different from other jobs I’ve had. Many of my past jobs I accepted out of desperation. My vision and values didn’t align with those organizations, and I was either ambivalent or downright cynical about the products and services they offered.
This time, I had already been working with the organization for nearly a year, so I knew what I was getting into. I had some grasp of the company culture and its values.
More importantly, the company I work for now gives me the opportunity to marry two of my deepest passions in life: music and writing.
But isn’t freelancing the best?!
There’s a lot of “leave your corporate job and monetize your side hustle” talk out there, especially on Medium. The “be your own boss” narrative is trendy and marketed as the answer to our generation’s anxiety about being a corporate slave. Freelancing is often framed as a ticket out of the misery that is being a cog in the capitalist machine.
And to many people, it could be the ticket they’re looking for.
But freelancing just wasn’t for me. I like my current job. I’ve never been at the same job for more than two years, and for once, I can see myself being here for a long time.
I’m not promising that I’ll stay in this job forever. Maybe at some point, I’ll go back to freelancing. Maybe I’ll go to grad school. Maybe I’ll become a stay-at-home parent. Who knows? I try not to plan life too far in advance; I like seeing where the winds take me.
Balancing Writing with a 9-to-5
This all being said, there’s still the problem of fitting personal writing into a day taken up mostly by a nine-to-five job.
It’s not easy and I’m still trying to figure it out. But I’m optimistic.
I’ve learned that for most people who aren’t geniuses (yours truly included), you have a choice: either half-ass a dozen things or whole-ass a small handful of things. I’ve half-assed writing a novel all my life, so I’ve made a binding decision with myself to buck down and get it done.
I can’t guarantee that I’ll become a famous published author, but I’ve made a commitment (and publicly declared it) to get my novel as far down the publishing path as possible. If I bail, well, that would just be embarrassing.
To prioritize this project, I’ve had to say no to a few things. I’ve had to break my heart. I’ve also had to sacrifice some leisure time and I’ve forced myself to become a morning person. I know I’m usually too tired after work to write, so I wake up before 6:00 AM to do it first thing.
As for accountability, writing on Medium and writing fiction is a self-motivated task, so I’ve had to think of ways to “manufacture” some sort of external pressure to keep me on my toes.
I started working closely with a critique partner who has been immensely helpful. Our partnership has been amazing, but it also comes with the caveat that I must uphold my end of the bargain. We set timelines for each other and we honour them.
As for writing on Medium, I took a break in April but this article signals my return! And I do plan to keep writing. My monthly newsletter necessitates that I send something to my subscribers, so having that nag me in the background keeps me productive.
Summing Up
For a long time, I thought there must be something wrong with me if freelancing didn’t work for me. I read so many blog posts about how freelancing gave people the freedom they’ve always wanted, how it made them rich. Surely there’s something wrong with me if I was unhappy at my old jobs…and unhappy while freelancing.
But when it comes to work and writing, there’s no one-size-fits-all. Some people thrive at freelancing; others need more structure.
I’ll be honest. I was ashamed to admit that I need structure, and I was ashamed to admit that freelancing hasn’t worked super well for me. Freelancing definitely has a “cool” factor and popular culture associates creativity with a lack of structure. (Creativity also has a cool factor.)
But hey, I can be creative and still like structure.
I’ve written about how constraints can encourage — rather than stifle — creativity. And I think that for me, having structure allows me to focus.
So, if you’re freelancing and thriving, congratulations.
And if you’re working a traditional job and thriving, also congratulations.
But if you’re not thriving doing what you do, perhaps it’s time to look for something else.
Li Charmaine Anne (she/they) is a Canadian author and freelance writer on unceded Coast Salish territories (aka Vancouver, Canada). Her work has appeared in literary journals and magazines and she is at work on her first novel, a contemporary YA about queer Asian skater girls. To read Charmaine’s articles for free (no subscription required), sign up for her newsletter.
