The Accidental Freelancer

When I went back to school for my Master of Arts in Media Production, I thought I had the perfect plan figured out.

Step 1: Move to Toronto (everybody says it’s *the place to be* for all things media, including my true love since 2014, podcasting.)

Step 2: Get my degree in podcasting (okay this doesn’t actually exist, but this program is the closest I can get and the admissions people SWEAR I’ll be able to learn how to make podcasts). (They turn out to be right, thankfully.)

Step 3: Find a sick network job and convince them to hire me to make cool shows, pay me lots of money, and give me healthcare coverage that lets me get regular massages (I love massages).

Well, you know what they say about best-laid plans. Turns out I should have left some space in the map for detours, dead ends, and a completely different destination.

Step 1 goes mostly okay – my boyfriend of 8 months packs up a rental minivan with me (yes, really, and we’re still together 6 years later) and together we drive the 36 hours from Calgary to our new exorbitantly expensive basement bachelor apartment in Toronto. ✔️ CHECK

Step 2 ends up being a year-long challenge that really tests my mental health, and COVID is no help…BUT I get it done. ✔️ CHECK

So if you’re keeping count, we’re 36 hours and 365 days into the plan. How long could Step 3 possibly take?

Year 1 – With the ink practically still drying on my brand-new MA degree, I apply to every podcast network job I can find. No dice. It feels like no one is hiring at all, and everyone is blaming the economy. It’s hard to live in Toronto with no family around at the height of the pandy, so we pack all of our stuff up AGAIN and drive back to Calgary even though I have no idea if there’s a career for me in the West.

Year 2 – I’m annoyed that I’m back in my hometown, and that I still can’t find work with an agency or network. So, I start taking on subcontractor podcast gigs. Eventually, I’m making enough money to quit my part-time job. I’m not working on shows I’m particularly passionate about, but hey, it’s something – and, it’s giving me more than 40 hours of work per week. In spite of this, freelancing still feels like something I’m doing while I wait for my “real job” to start.

Year 3 – Feeling overworked, overwhelmed, and more than a little apathetic, I quit my biggest show. Maybe I just need to start fresh – that’ll fix everything. Too bad there’s no network OR freelance gigs now. Just as I’m about to hang up my producer hat and look for ANYTHING else, one of my clients asks me if I’d be interested in developing a new show that would give me nearly year-round income and a more regular schedule. Plus, I’d own the production schedule outright – no more subcontracting. Of course I say yes, and the first thing they do is send me to Argentina for a recording. Maybe being freelance isn’t so bad??

Year 4 – The freelance career I almost gave up the year before is going shockingly well. I’m still applying for network jobs, though, because I still want to become a “real” producer. I sign a contract with a production company who says they’ll have a show for me soon. I wait, and wait, and wait – but I have lots of freelance work to keep me busy. Suddenly, I am TOO busy. I’d heard people talk about burnout, but I didn’t know that it would make me fantasize about not having to wake up in the morning. I make more money than I ever thought I would…and end up walking away from half of my contracts again, because I’m afraid of what will happen otherwise.

Year 5 – A friend of mine offers to coach me through making my business more sustainable. The timing couldn’t be better, because that production company who hired me folds – taking my patience with it. “Fuck it,” I say, and finally embrace a career that’s been half a decade in the making. I start going to podcasting conferences, where I meet a ton of cool industry people. A friend of mine asks me to speak about freelancing at an event. Afterwards, someone thanks me for making them feel less alone. The thought that maybe they won’t have to struggle the way that I did makes me so happy I want to cry.

Year 6 – I decide I need a new Step 3. After 5 years of waiting for permission to feel like a “real” producer, I finally figure out that I’ve been looking for validation in the wrong place. I always joke that I had to hire myself because no one else would…but I’m actually a pretty good boss.

Step 3: Find a network job ❌ NOT NECESSARY

*New & Improved* Step 3: Keep freelancing. Join forces with another badass freelancer and start a production company. Teach podcasting at a university where I not only love the work, but I also get discounted massages. Make other freelancers feel less alone by starting this newsletter.

It took me 5 years in a career I didn’t think I wanted to realize how lucky I actually am. I did a lot (and I mean A LOT) of stuff the wrong way, or the hard way, or both. But I didn’t know what I know now: that it doesn’t have to be unenjoyable. You can actually like freelancing.

So, if you’re an old-hand freelancer looking for solidarity and better strategies, or a brand-new freelancer figuring out whether you want to dip a toe or cannonball into this weird little pool – welcome. Hopefully my experience and that of all the other very cool people I’ve met can be of use to you. Freelancing has become more than a job for me; it’s a community that I’m proud to be a part of. I like freelancing – and you can, too! So, let’s make your freelance career into something you can actually enjoy.

x Jess