15 Years of Freelancing: A Reflection

When I started freelancing, I don't think I realized how successful I was at it. My goal was to build a huge email list and sell info products, something I never quite managed. My interests were so versatile that it made more sense to borrow other organizations' built-in audiences as a freelancer. I even had one or two failed crowdfunding campaigns. For a while I was doing a bit of content mill work, which paid pennies but if you worked fast paid a higher hourly rate than I could have gotten at the local coffee shop. (Lesson: You could be doing everything right even while being told it is "wrong.")

Eventually I started making as much as I had teaching. (A low bar, I know.) Then I made double that, and sometimes triple that. I juggled freelance writing with a managing editor gig at a fitness journal. I wrote an online textbook, negotiating for an advance in case it didn't sell. (It just sunsetted this year, but I was making a cool five figures in royalties each year.) I took gigs for agencies managing brand blogs, making sure they didn't overlap with anything I covered editorially. I wrote a weekly security news column for Wired and did group chats about hacking tools in Mr. Robot so I could write about things I cared about while doing other work for the bills. I was always hustling. I tried to send two pitches and two follow-ups a day if I didn't have enough work lined up or coming in. I didn't care as much about the pay per word but would keep track of the pay per hour. I quietly made a good living off of work other people thumbed their noses at, pitching those $400 and $500 posts that had less competition than anything $1/word and up. (Lesson: You can juggle lots of beats while everyone else is "specializing." And you can ignore the finger wagging and sometimes take "low paying work" that's fast and steady.)

I quit clients constantly because they paid late, didn't pay enough, or were more trouble than they were worth. I honestly didn't have to worry about finding enough work... but it may not be work I actually enjoyed. I spent a lot of time honing my craft, going to conferences, finding ways to automate my past due notices when I was inevitably paid late. I started attaching invoices to the emails where I attached my writing, to stop the invoices from "getting lost." (Lesson: if you are constantly improving your skills and networking, you can also improve your client roster to people who pay on time or who you simply prefer working for.)

Eventually I felt that I'd hit the ceiling on freelancing. I was doing more work--and more valuable work--but there wasn't budget for higher pay. I went back to school (after deferring for two years until I could go on a scholarship) and got my Masters degree at Cronkite. I was hoping to pick up some data journalism skills, some visual journalism and audio journalism skills, all to supplement my writing and reporting. I did learn a thing or to but did not end up incorporating any of it into my work. Still, I think grad school helped me hit the reset button and I settled into a full-time job. (Lesson: Don't pay for grad school for journalism if you can help it. Get an assistantship instead. Also realize there is a ceiling to what you can earn as a freelancer, and you may not want to start from scratch on new skills depending on how long you've been doing this. And you probably can't learn them well enough in three semesters.)

I sometimes wonder if I would have been able to make it as a freelancer if I had made my attempt in 2024 instead of 2009. So many publications have cut back on freelance work, lowered their rates, or taken more writing and reporting in house. The competition is fierce, with an ever-increasing number of laid off journalists throwing their hat in the ring along with everyone who has ever had a side hustle. The paid newsletter space is saturated. Even at my day job I've pivoted away from pure journalism to product and program management with a side of policy work. I've worked on my speaking skills and panel moderation skills, taken courses on communication and leadership skills, and studied cybersecurity, source protection, physical safety. (Lesson, for all of us: always keep learning and pivoting.)

The whole time I've worked full-time I've continued freelancing. This is for multiple reasons that I've heard discussed when people are deciding which projects to work on as a freelancer. Pay, prestige, and pleasure. (I've also heard this referrred to as "one for the reel, one for the meal, one for the feel.") Sometimes there are entire beats or topics you can't write about for your day job (if you write for your day job at all), whether it's for the sheer joy of it or because it can create some kind of meaningful impact. Having side income is always nice, and it's much easier to ramp up a freelance or consulting business when needed (due to a layoff or furlough) if you have a current client or two. One never knows what tomorrow may bring. (Lesson, or rather an opinion: It's good to keep your options open!)

In the past couple years I've had just a handful of clients, and I have been thinking about how to ramp that up as I only have two projects in the works, with the possibility of a third. This is the lowest amount of work I've had lined up since I got started. One of the project is a book that would lend itself well to video courses. And, of course, consulting is also always on the table. Though I'm extremely picky about my clients, I do still take the occasional meeting. As I said last year, it is very hard to quit.

It's been a great 15 years. Here's to the next 15.