14 Years of Freelancing: A Reflection
4 min read

14 Years of Freelancing: A Reflection

14 Years of Freelancing: A Reflection
by Watchduck, CC BY-SA 4.0

Fourteen years ago, after I realized teaching middle school wasn’t my thing and left sunny Tucson for the sad, cold, and lonely city of Eau Claire, I started freelancing full-time. I had done a few stories here and there, mostly about things like mixed martial arts and Olympic weightlifting, but when I found myself without any job prospects beyond a part-time minimum wage job at a bakery, I decided I could do better.

I entered my career at entry level wages, pumping out content mill posts for $7.50 and $15 a pop, ignoring seasoned freelancers who told people not to take work at that rate (and quickly scooping up the 10 cent a word jobs they thumbed their noses at). I picked up some steady editing gigs, so I knew I could always pay my rent. I traded my flip phone for a smartphone so I could leave the house. Within a year I was making as much as I had as a teacher, working fewer hours. (I’d also supplemented my teaching salary by teaching Sunday school at my local synagogue and by working as a promo model offering food samples and free shirts and plastic trinkets at various grocery stores and bars, so I was used to constantly working). I started teaching weekend classes for adults, did managing editor work for an agency, and gave up on all of my side hustles involving things like teaching herbal first aid. 

When I started I wrote about anything, for anyone–the beekeeping magazine, the yarn magazine, you name it. I wrote about social media and about content marketing and did a bunch of ghostwriting for health blogs. I eventually found myself making six figures or close to it, but was also working every single day. It took me longer to realize I could take breaks. It took me even longer to realize I could say no. And, of course, I always had to fight to get paid. I even had to take two separate clients to small claims court. (I won both times.) I switched to invoicing software that would automatically send reminder and past due notices. I would also print out the notices and send them certified mail when I needed to. I hardly ever got paid on time.

I transitioned to covering privacy and security because I was obsessively researching it for personal reasons–and realized I had to write about it if I wanted to make rent that month because this had taken a lot of time. I soon decided it was a lot more interesting than what I had been covering. 

Freelancing meant I had to buy my own health insurance, for years. It meant I had to eventually pay someone to follow up on unpaid past due invoices because I would get irritated, which killed my productivity. It meant I had to go to cafes or cowork to remember what being around people was like, but that dozens of random people I respect would hop on a call to answer questions, for free, pretty much anytime.

Freelancing has earned me distrust from people who should probably be more worried about what they post publicly, but it’s also gotten me out on a food and cheese tour in Madison, exploring Huatulco, and a free visit to a very nice Ayurvedic destination spa to write about for a trade journal. I’ve gotten to interview some of my heroes and written investigative stories about people’s now-former heroes. I’ve done awkward video interviews of MMA fighters while getting paid more for mileage than I did for the 12+-hour days and I’ve signed five-figure contracts, and sometimes the five-figure contracts paid less per hour than the 10 cent a word pieces. I’ve stayed up til 2am every week writing a column because I didn’t get approval on the topics in time. In my worst experience, I dealt with an editor who decided to ghost us for months on end, on a very secretive and high stakes story we weren’t sure was even going to get published. It was worth it, but barely–we published in spite of said editor, not because of him. 

My work has shown up in amici briefs and in reports from the United Nations Commission on Human Rights. It’s led to FTC settlements. It’s gotten people to decide whether to do business with certain companies, and when not to. It’s led to hours-long phone calls and interesting discussions at parties with loud music blaring, making it not conducive for conversation. 

I have made a lot of freelance friends, and sometimes have people to join for tacos and cocktails as I traverse the country. I’ve also dealt with competitive freelancers, who are quick to swarm editors at conferences as they’re trying to leave the room and will give you dirty looks if you happen to already know someone. The freelance community is far more welcoming than it is cutthroat, but I guess it draws all types.

I left full-time freelancing because I’d felt like I hit the ceiling on it–I was asking for fair pay but it was outside of people’s budgets. I went back to school to try to learn some new skills and revamp my career, but continued freelancing. I took on some contract work, and kept freelancing. Eventually I decided to take a job. Still I continue to freelance on the side, even while consumed with full-time work and volunteer work and a rich social life and a million hobbies, even while in an intensive grad school program and an assistantship. Because no publication will have room for every story idea. Because you just never know when you’re going to be on the list of layoffs next, and it’s better to start from somewhere, even if it’s just one or two projects a year. Because everyone can use a little extra cash. 

This past year will be the least I’ve made freelancing since I started, but $7000 isn’t nothing, which is what I made in textbook royalties, along with a single project with a non-profit and an additional article. 

I know that if I do find myself in need of work, I have somewhere to start. But I’m hoping to pull back even more. I’m hoping to spend more of my spare time learning ukulele or decorating cookies or practicing magic tricks or trying to figure out how to design those soft circuits and e-textiles. 

In 2024 I am working on my book, updating my textbook, and finishing up one final freelance project… but I’m sure more will find their way to me. It is very hard to quit.