On Taking the Leap Into Freelancing

I’ve done a lot of scary, crazy and bold things in my now 7-year career as a freelance journalist, but none more so than kicking off the career itself.

I tested the waters as a freelance journalist on a part-time basis in the late autumn of 2012, and took the full plunge early in the New Year. Studies show that most choose self-employment out of a disdain for their boss/job, for more control over their careers or to make more money, and I guess my reasons were a combination of all three. At the same time I’ve always been very independent, so much so that when the concept of freelancing was first introduced to me it felt like an inevitability.

In fact, when my journalism professor first introduced us to the concept of freelancing (shout out to Professor Mark Kearney) he didn’t sugarcoat it one bit: he told us that finding work was a full time job unto itself, that freelance rates haven’t budged for the better part of the last half century and all the challenges associated with fluctuating income.

It sounded terrible, but inevitable. I knew myself well enough to know that it was only a matter of time before I went down the path of self-employment, though I wouldn’t have guessed that time was just two and a half years after graduation.

It didn’t help that I spent the first 8 months of those post-graduation days helplessly unemployed with absolutely no prospects, or that the first gig I did land was for a “digital content” studio that only dabbled in what I would call traditional journalism. That constant strive towards independence had also compelled me to move out of my parents house and into a tiny downtown condo, long before I could afford to do so.

Through my first year of formal employment my boss “started me off” with a pretty low salary but promised a significant raise for year two, approximately 30% more than what I had made in year one. I spent a year on the fence about that job, often thinking about jumping ship, but the promise of a higher salary gave me just enough motivation to soldier on. Of course when the longest year of my life finally did come to an end, the raise that was offered to me was closer to 5% accompanies by the promise of another generous raise in just one more year. I reluctantly accepted it.

I was overall pretty unhappy with the lack of agency I had over my own life, when a former classmate mentioned that an editor of his was looking for some outside help with a project at the Toronto Star’s small business section. I jumped at the opportunity to work for the country’s largest newspaper, well before I figured out how I’d do so while stuck in a tiny, open-concept office from 9 a.m. to 6 p.m. with a boss who wouldn’t be too fond of me side-hustling for another outlet. I could do the writing portion during evenings and weekends, but I needed to speak with sources for these stories, and it seemed unlikely that I could reach them outside of standard business hours.

My first solution was conducting interviews in the stairwell of the office during lunch breaks, but that quickly proved unsustainable. Not only was there a high likelihood of getting caught but the background noise of workers marching up and down the steps during their lunch breaks made it difficult to hear my interview recordings clearly. Eventually I found a new trick. 

My small business stories required interviews with experts in Canada, but they didn’t necessarily have to be in Toronto. If you looked back on those stories (i don’t know why anyone would) you’d notice that most of my interviews were with sources based in Vancouver, whom I’d speak to after 3:30pm Pacific, well after I made it back from work on the east coast.

I kept that up for a couple of months until my uncle connected me with an editor from Canada’s second largest newspaper, The Globe & Mail. He was a business reporter but didn’t recommend that I continue pursuing business journalism, seeing as the field was already crowded and more welcoming to MBA graduates than journalism majors.

In that conversation, however, I told him that I was hoping to eventually become a remote working, full-time freelancer. “Those are all the buzz words our careers section editors are struggling to write cover,” he told me. “You should speak to them.”

So he connected me with the careers editor of the Globe and Mail, who gave me my first assignment in early 2013 with a one-week deadline. For that assignment I took a sick day from work and did the whole thing in one day, which impressed the editor enough to give me another try. After a couple more it started to look like I might actually be able to cover my rent as a freelance journalist, as long as I was fine with a food budget of $25 a week.

Pro-tip for new freelancers; you can get a half dozen bagels for about $4, a package of cheese for $5, and some vegetables for another $5 and if you really want to live large, some canned tuna and mayo for about $7. Throw in a dozen eggs and some bread and that should cover you for a week.

What can I say? Some dreams taste like champagne and caviar; mine tasted like melted cheese on a whole-wheat bagel with avocado, tomato, onion, and a on really good week some tuna.

In January of 2013 I earned enough as a freelancer to cover my rent. In February I made $200 more, and by March I cracked the $2000 mark, but only by $10. That’s when I decided to quit my full time job, and take the leap into freelancing.

The first month I put all my focus and energy into freelance, in April, I earned nearly $6,000, though it would be a long time before I saw a month like that again. Through the remainder of the year my salary fluctuated widely, but in the end I earned almost exactly what my former boss had promised I would make that year, before changing his offer.

When he rescinded his offer I couldn’t have imagined making that amount on my own, while working for myself and doing work I actually wanted to do.

After that my mind was made up: I was going to do this for the rest of my life.

Once I started freelancing other opportunities started to arise too; suddenly I could travel, I could pitch any publication I wanted and I could even start pursuing my dream of being a music reporter. You can read more about that in my next post.

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