How To Freelance on Top of a Full-Time Job
An expression I’ve never quite understood was the cliche about “having your cake and eating it”. I mean, isn’t the whole point of possessing cake the eating of it? And can’t cake always be “had” unless you’re in a food crisis and you don’t have access to butter, eggs, sugar, flour et cetera? I don’t really get it.
A better phrase that captures the same essence is Yogi Berra’s famous malapropism: “When you reach a fork in the road, take it.” Professionally speaking, I’ve long sought to “take the fork”, that being the point of divergence between the security of the nine-to-five gig and the adventure and growth potential of the freelance life. My success at this has varied over time, but I think I’ve finally landed on the right balance between the two.
When I first started freelancing, I had a full-time job as a high school English teacher in a Tokyo suburb. I later left this job for another full-time opportunity as a translator and copy editor for a boutique translation firm in downtown Tokyo, fully embracing the Japanese “salaryman” role. At the time, my freelance output was fairly slow—a magazine article here and there—and this pattern persisted following my move back to Canada and my entry into the communications scene in Edmonton.
There have been a few periods of my life when I was a full-time freelancer, but I always seemed to return to full-time employment. I still like the security of a full-time gig. I like health benefits and putting away into my public-sector pension. I also like being a member of a team; freelancing can be a pretty isolating experience. I also like not having to hunt for my dinner Neanderthal-style all the time, which is the reality of being a full-time freelancer. At the same time, though, I enjoy the adventure, stimulation, and, yes, compensation that comes with having a side hustle.
I have indeed demonstrated that at least in your professional life you can “take the fork” and proceed along both prongs for quite some time. At least it seems to be working out for me so far.
COVID Changed Everything.
The COVID-19 pandemic transformed a lot of people’s professional lives. In my case, my post-pandemic professional life would be utterly unrecognizable to my pre-pandemic self, and I indeed find myself hard-pressed to remember things having ever been any other way.
Until the end of 2019, with the exception of brief stints in 2014 and 2016 when I was fully freelance, I always worked in an office. Working on-site Monday through Friday from 8 to 4:30 or whatever placed great limitations on what I could do as a freelancer. Sure, I still had my evenings and weekends, but many hours of my week were being eaten up by commuting, prepping lunches, and other tasks associated with going to the office. Not only that, scheduling client meetings and interviews during normal working hours was virtually impossible, placing serious limitations on the kind of work I could do.
In the earliest phase of the pandemic, I got my first ever fully remote position as a full-time writer and communications strategist for Vista Virtual School, Alberta’s only entirely online K—12 school. After nearly a year of this, I got a new job with Covenant Health (where I still work to this day), but I succeeded in keeping Vista Virtual as a part-time freelance client—my first attempt at truly “taking the fork”.
When this contract came to an end, I parlayed my remote work experience into a part-time gig with a tech company in Montreal. This job ended up meshing perfectly with my full-time role at Covenant. Because this client was situated two time zones ahead of me, I could easily schedule client meetings in the hours before I was on duty for Covenant, and the lack of commute meant I could do client work right up until 7:59 am before switching gears for my day job. At times, I would—and still do—log two hours of client work before I “show up” at my day job, by which time I’m revved up, fully caffeinated, and ready to do my best work.
These days I aim to log around 20—21 hours of client work a week, which averages out to around three hours a day. I mostly accomplish this by front-loading my days with client work, as I tend to be a morning person and prefer to save my evenings as much as possible for other activities, like working out, cooking, household chores, or just relaxing—basically anything that doesn’t involve starting at a screen. I currently have clients on both coasts of North America, meaning that I tend to have client meetings before and shortly after my regular work hours. I also use my lunch breaks for client meetings—at least when I have to.
This structure and pace of work would be virtually impossible if I had to commute to a physical office every day. I still like going in occasionally, usually once or twice a week, but I found I took to remote work like a duck to water right from the start, and at this point I can’t imagine working any other way. It would have to be an absolutely amazing job offer one way or another (or some sort of dire straits in my life) that would persuade me to go back to my pre-COVID mode of working. Barring some disastrous setback, I don’t see that happening.
I’m extremely lucky to be able to do what I do at the pace I’m doing it. Most people don’t have the luxury of being able to roll out of bed, do a bit of morning meditation and journalling over coffee with a dog in your lap, get showered up, and then sit down to work on creative writing assignments for a couple of hours before your main gig starts—which also mainly consists of writing assignments—all without the necessity of leaving your house. I’m also not starved for company, as I get to have lunch and dinner with my wife, who also works from home as a private music teacher, which means a steady procession of students in and out of the house during the week.
It would be in poor taste for me to express gratitude for COVID, as the disease produced so much suffering for so many people. That said, I AM grateful for the way it transformed the work world, at least in my world. My life, while busier than it’s ever been, is far richer and more stimulating than it ever was pre-COVID, and I wouldn’t trade my current reality for anything that came before it.
How To Deal With It All
Those of you reading this post might be thinking, “Wow, this guy must really have his poop in a group! He must be really organized and on top of everything!”
Sigh. If only.
To my credit, I’m far more organized now than I used to be, but any organizational guard rails I have in my life have been hard won. It was about a year before the pandemic hit that I received a medical diagnosis that explained, well, everything: ADHD. My default brain state is chaos, and to say that organization doesn’t come naturally to me is a colossal understatement. While I’ve always been an excellent writer, I also used to be a disaster at following instructions and meeting deadlines, which probably explains why my previous attempts at going fully freelance ended in failure.
My ADHD diagnosis has been a major factor in my decision not to abandon the security of the nine-to-five job. The thought of not having that structure in my life, to say nothing of the fact that I would have to deal with all my own health insurance stuff and pension and everything else an employer deals with for you, fills me with anxiety. While I consider myself pretty entrepreneurial, business management has never been my strong suit, and there would invariably be a lot more of that if I were to be fully self-employed. The more life security stuff I can outsource to other people, the better I feel.
That said, maintaining an active freelance practice on top of a day job does require a fair bit of organization—certainly more than I’m naturally inclined to possess. One of my daily practices that has greatly enhanced my organization is daily scheduling. One of the last things I do before I go to bed is plan out the following day, with everything scheduled down to 15-minute increments. This is about the only way I’ve found I can do everything I want to do in a day. Of course, things come up and I’m not always able to follow my best-laid plans to the letter, but, like a teacher’s lesson plan, it provides a structure to fall back on and helps you prioritize tasks.
Visual cues help me keep everything in focus (I use a big whiteboard to keep track of my innumerable writing assignments from various sources.), as do a range of technological tools. The ability to merge multiple Google calendars into a single calendar was a game-changer for me, and I’ve been fortunate that most of my clients are primarily Google and Slack-based in their communication, platforms that are conducive to flipping between accounts. I’m also a prodigious user of alarms on my phone, which I find helpful for transitioning between tasks, particularly as my ADHD hyperfocus leads me to get completely absorbed in tasks.
Whenever possible, I always seek to have standing weekly meetings with key people in both my day job and at my freelance clients. Regular meetings help me keep the various assignments I have across my professional landscape top of mind and help me talk through problems out loud. The advent of AI-based transcription software for meetings has been absolutely life-changing for me, as it’s obviated the need to take extensive notes in meetings. And when all else fails, I can always ask ChatGPT what it thinks I should do with a specific writing assignment, or in my life in general.
I’m not entirely sure how I’m managing to do everything I’m currently doing, but I seem to be managing it all. I don’t know how long I’m going to want to keep up this pace of work, but for the time being I’m enjoying it—and enjoying the results of it. When it comes down to it, I love to write and I’m happiest when I’m doing a lot of it, which is why, on top of everything else I do, I also maintain this blog.
In the wired, AI-enhanced world of 2024, it is indeed possible to “take the fork” in your professional life, provided you enjoy what you're doing and are getting enough screen-free time in your life. I certainly wouldn’t want to be alive at any other time in our history, despite our world’s innumerable problems. These tools exist to help us be all we can be. We might as well use them.
