So, You Want to Quit Your Job and Become a Freelance Writer

In 2021, I left a job that had become toxic. The Covid-19 pandemic, family reasons, and a mid-life crisis also played a role in my decision. Yet fundamentally, the despair caused by devoting 25 years to a calling that had become destructive and mean was the primary motivation for me to upend my life at mid-career.

Doing so was difficult and terrifying, at first, even though I knew I would have a roof over my head, supportive family members, and enough money to pay my basic bills into the foreseeable future.

Nothing that has happened since has caused me to regret my decision to get out of a situation that had become demoralizing and untenable. I miss the job as it once was. I do not miss what the job became or what it was doing to me.

That said, nothing about this change has been easy, either. I want to share a few things I’ve learned about being a freelance writer in case they are helpful to someone else. Some of these lessons might also be of interest to other professionals who yearn to try something different.

Ultimately, you must decide to leave a job on your own. You can ask for advice, ponder your options, draw up a provisional budget, and run-through scenarios in your head for months or even years. But at some point, you either jump or you do not.

There is no shame in staying put — and resisting the siren song of the gig economy — even if you no longer love your job. Stability has a lot to recommend it.

For those who do decide to jump, here are three things I’ve learned along the way:

1. Changing from a steady paycheck to freelancing will be even harder than you — and the people who love you — anticipate.

I enjoy writing and love the freedom that a freelance life can provide. However, I admit now what I could not admit for at least the first twelve months into this adventure: it was great to have a title, embossed business cards that I did not pay for, an IT department to call upon, and an office. I took all of that for granted.

The reliability of a fortnightly paycheck was also lovely, but I knew I had to relinquish that in order to get my life back. What surprised me was how much I had come to rely on my title and professional affiliation to establish my credibility to others — and to myself — without any further effort on my part.

Without that shorthand, though I was still the same person who had done everything listed on my resume, it was as if the professional me had vanished into a void. I am still learning how to reclaim everything I wrote and did when I had a mainstream job and repurpose it for this new life. I am also still learning how not to start every interview with, "When I was an academic . . . "

2. Though their pay is often low, and they have no authority, the writer usually ends up being the single most important person in the corporate workflow at the crunch points. 

It may be difficult for the reader to appreciate how naïve I was when I started this new life. Looking back, I can barely believe it myself. Despite having navigated the slippery shoals of academia for over two decades, I was stunned at how awful a bad freelance client can be — mean, petty, and spiteful.

Content mills — or, more neutrally, writers’ platforms — sometimes connect you to good clients. I have had a few and valued them greatly. However, between taxes and the fee that the platform charges to broker the client-writer relationship, you will likely find that your earnings rapidly drop to levels that are demoralizing.

This is not just a matter of ego, and please don’t let anyone tell you that it is. The hard truth, in my experience, is that a freelance writer who works through a content mill is usually the last person to get the material and the least remunerated.

Yet deadlines in this world suddenly become “critical” and inflexible. There will be no quarter given to contingencies such as the flu, a family emergency, or your wi-fi breaking down. I am happy to admit that I probably did pick up a few diva-like behaviors as an academic. Yet this situation has little to do with that, and everything to do with the assumption that writers are disposable.

No matter how long the project has been in the pipeline, your ability to turn out flawless copy by an immovable deadline suddenly becomes crucial to the company, the shareholders, and even the survival of capitalism as we know it. If you dare to interrogate this situation, you will be blacklisted. 

Forget all you’ve read since 2019 about “quiet quitting,” work-life balance, or flat organizational charts. There will be none of that here. Indeed, Charles Dickens or Karl Marx, magically transported to the year 2024, would recognize the basic, exploitative working principles of content mills within a nanosecond.

3. Freelancers are gaslit often by clients, intermediaries, and even other freelancers.

No matter how good your past performance, every new job with a content mill starts the clock and performance review anew, like some nightmare version of Groundhog Day.

This will be the case regardless of whether the material is more difficult than the brief promised. It will happen though the amount of money that is sub-sub-subcontracted to you is miniscule compared to compensation taken by all the intermediaries that passed the project down the line. It will even happen when the expectations placed on you, timewise, defy the laws of physics.

I expect there are freelancers out there who never drop a stitch and who just adore their wonderful clients. Indeed, I know that there are because these freelancers stand ready on comment boards to shut down anyone who dares to suggest that fault can lie anywhere other than with the writer.

These angels in the content mill are, in fact, so predictable and quick to squash even a hint that the machine might not be working fairly that one is tempted to wonder if perhaps they are paid corporate shills. Oh, but surely that’s paranoid. I cannot conceive of a company that might want to depress workforce discontent by isolating critics from the ranks.

If you are that freelancer who routinely clears $5,000, $6,000, or $9,000 a month via a content mill, all while writing a novel, running a coaching business, and successfully day-trading, please do not tell other writers that they simply need to be more organized or work harder. Few of us want to hear about the 6-figures you make annually through Medium, either, since those days--even if they existed once--seem long gone. 

Finding Your Way

A content mill is designed to churn through talent in a highly competitive market. Some people may thrive within the system— and good for them — but that does not necessarily mean that the system is a good one.

Let me conclude by reiterating that I do not regret my decision, at mid-life, to start over. I do not even regret working with writers’ platforms as a first step toward my new professional life.

I did want to share my experience, though, because nothing about freelance writing is easy, no matter what the glossy magazines promise. The path can be exhilarating, rewarding, and life-reaffirming. But it is never easy. Please don’t let anyone tell you otherwise and please learn to recognize gaslighting when it happens to you.