A Year Off The Beaten Career Path
Rome, the “eternal city”. We drank tiny espressos and meandered past open ruins, pistachio gelato melting onto our hands. We paid a second homage to the eternal city’s treasures — the colosseum, the Trevi Fountain, St. Peter’s Basilica — edging our way back for picturesque vantages after just a few minutes in the thick of it. It wasn’t Rome we had come to see; The New Romantic was playing at the Festa del Cinema di Roma and I had yet to see my first film projected onto a big screen.
This time last year, the Sudbury, Ontario shoot had just wrapped. Even after 8 weeks of under-sleeping and over-caffeinating, I was on a high. I’d just been part of making a movie with a ragtag crew of creatives, from whom I’d learned a million things. I suddenly felt certain about my direction; that I was where I was meant to be. Yet two weeks later, I handed in my resignation letter. Three weeks after, I was unemployed and moving things back into my parents house. Two days before Christmas, I was bound for India with a one-way ticket. It was a time of sweeping change and I’d be lying if I told you that it didn’t feel great. Liberating. Thrilling, even.
Because until then, I had gone about life in the expected manner. I graduated from high school with scholarships and went directly to university. I graduated somewhat according to plan, started an internship that fall, and leveraged it into a full-blown 9 to 5 by New Year. I set forth on a charted course; yet I was always finding ways to divert from that path, even if only momentarily. I spent two semesters abroad where academia took a backseat to endless surf trips and tipping back two-euro wine bottles before an Eiffel tower backdrop. Instead of interning close to home, I opted for a position with Los Angeles Magazine. And when I did return, I used each 2-week vacation to float in the Dead Sea or motorcycle across Myanmar. It was on such a trip that I was taken under the wing of a Danish ‘bike gang’ that called themselves ‘Trækfugle’, aka. ‘migratory birds’. It resonated with me—that birds were wired to make for another home whenever shifting seasons beckoned—and I spent the rest of the day envious of them. But then I returned to my job, my apartment, and my routine, picking up where I’d left off without so much as a second thought.
A lifestyle shift didn’t seriously occur to me until this time last year. By working on the film, I hit the ground running in a new place, surrounding by new faces, with what essentially turned into a completely new job. The change was revitalizing and by the time I was home, previous conversations shared with my partner Luke about integrating travel into our lifestyle tugged at any lingering roots. Once the idea of embarking on an adventure of my own design, shaping my own environment, and directing my own career took hold… well, here I am exploring beautiful Slovenia. What I have yet to share is my journey through this first year of freelance work. And though I’m still in the early stages of what I predict will be a long-term affair, I hope you gain something from my stumbling blocks and small victories.
TAKING THE PLUNGE
When I resigned from my full-time job, freelancing was still a very loose construct in my perception. It seemed like something reserved for the Instagram models, social media influencers, and digital nomads of the world. Sure, freelance work was out there somewhere, but it was a distant and intangible thing. I left Vancouver with savings meant to last until we arrived somewhere in Europe, where I knew I could get a working holiday visa. I was prepared to work any job I could get, and also ready to draw on my serving experience if I had to, in exchange for a new experience abroad. But as I relaxed out of my former routine, the idea of controlling my own schedule appealed more and more.
With no idea of where else to begin, I read The Wallet Moth, a blog about the freelance lifestyle written by someone Luke and I had met in Chiang Mai on our “fifth date”. Yasmin’s site gave me some ideas about online jobs that I had transferable skills for (virtual assistant, writer, editor, English teacher). From there, I googled things like “freelance work” and spent hours aggregating information. During the research phase, I read endless articles with click-bait titles like “8 Companies with Remote Editing Jobs You Can Do From Anywhere” and “72 Best Freelance Jobs Websites to Get Remote Freelance Work (Fast)”. Then I started applying for anything and everything I could, hoping something would land.
Finding meaningful opportunities didn’t happen overnight. In the beginning, I ran into a few scams that take advantage of hungry job seekers. I failed several editing tests and went through a period of second-guessing my entire college education. I also had some false starts; I made it through the multi-step interview process for a company called Golden Voice English, whose e-learning platform allows freelancers to teach English to Chinese grade school students. I put hours into learning their interactive system and PowerPoint curriculum but despite my wide open availability, a single student has yet to be assigned to my virtual classroom. Further research online (which I should have done from the get go) showed reviews from many people describing how the company tends to over hire. When I inquired about more classes, I was prompted to study and test for a “new” curriculum program without any guarantee I’d get students in my classroom. Needless to say, I requested to terminate my contract…a process that is still dragging on. Luke found more opportunities from the get go and at one time, he was juggling assignments from four companies: Cactus Communications, Enago, and Wordvice plus a remote editor position with a sustainability firm called South Pole (he continues to work for South Pole, taking on the occasional Cactus project).
What did eventually work for me was UpWork. I had forgotten all about signing up because the process of bidding for jobs sounded daunting. But one day, I got an e-mail inviting me to apply for someone’s script coverage gig. The pay was average and UpWork took a 15% cut (which was recently raised to 20%), but US dollars go a long way in India. Plus, reading a script at a beach front cafe would at least keep my skills sharp. In the beginning, the work came in slowly and didn’t amount to a liveable income. I also agonized over the job proposals I sent, and the ratio of applications to actual hires. But the more experience I gained, the more contracts I seemed to close. You can find any type of freelance gig there, and I mean any. Luckily, there are more script projects than Rainbow Mayan Vampire fiction.
There have been challenges and disappointments—I’ve been lowballed, ghosted, led through a lengthy interview process only to learn the client didn’t have funds for the screenplay yet—but with some sifting, I’ve managed to find the right projects and negotiate fair contracts for a combination of weekly and one-time assignments, covering meals and rent. UpWork has also led to my biggest projects including my first TV Pilot, an adaptation based on The Game: Nothing Is As It Seems by Heather Noël, and a short fiction piece to be published by Endless Ink.
While this style of freelance work provides flexibility and freedom, it’s a laborious process without any guarantees. It’s been a good start towards bridging my film career goals with a freelance lifestyle. Taking the next essential step, I found a list of production companies in Slovenia and reached out to every single one. I didn’t hear back from anyone until after summer holidays and out of thirty personalized emails, only two meetings surfaced. But from those two meetings, I’ve completed a commercial screenplay assignment, two series bible projects, a couple editing jobs, and lined up production assistant gig for a feature film shooting in February—not to mention gained a new climbing buddy for us.
While my time at Drive Films gave me a valuable foundation, branching out on my own has taught me things I couldn’t have learned elsewhere. First of all, I discovered how to hustle. That is not to say I didn’t work incredibly hard at my previous jobs, but eliminating the security of a guaranteed work and bi-monthly paycheques gave rise to a whole new work ethic. Being honest and critical with myself through this process, I’ve learned the value of my skills and time. I’ve also figured out ways to push self-doubt away when it surfaces, clearing an attainable path to my goals. I expect the learning curve will be ongoing, but so will my growth. Just one year of experimenting has led to my first screenplay credit and published short—opportunities I’d have missed had I stayed “on course”. I have no way of knowing what lays ahead, but that’s precisely what fuels me to be creative and productive in the present.
I’m not saying freelancing is better than other forms of employment, or the best fit for everyone. But I have enjoyed becoming my own boss, choosing projects I’m passionate about, and directing my own career growth. Without a daily commute, I’ve been saving time, money, and carbon emissions. I’ve also had the flexibility to mix online courses into my workday, bake banana walnut bread between articles, and work on the train ride to Rome for a mid-week getaway. Freelancing has not been without challenges or sacrifices or existential crises…but through the experience, I’ve taken my first steps towards a lifestyle of my own design.
If you are itching for a change, information, resources, and possibilities are out there—but it all starts with knowing yourself and pinpointing the lifestyle you want. And talking about it helps, so please feel free to reach out.