Money Moments

I tried to file my own taxes as a freelancer. Then the CRA letters started arriving

By: Anna Fitzpatrick on April 9, 2019
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Money is a funny thing. It’s tangled up with just about every aspect of our lives — from where we live, to what we eat and the quality of our relationships — so it’s no wonder that all of us have opinions on what we should do with it. But what shaped our approach to money in the first place? What pivotal moment forever changed the way we think about our finances? To explore these questions, we’re introducing MONEY MOMENTS — a regular series where Canadians reflect on a moment in their lives that shaped their attitudes toward money. 


I started working my first “real” job at the age of 15, trading in my sporadic babysitting and lawn mowing gigs for a hairnet and the chance to perpetually smell like hamburgers. Still, I took pride in my fast food job, feeling very adult for collecting a biweekly paycheque, an employee ID number and an annual T4 slip. The following year, I filed my taxes for the first time with the help of my parents. It took 10 minutes and I got an $80 return. I quickly came to associate tax season with free money. Unfortunately, like staying out past 11 p.m. and eating a pint of ice cream in one go, filing my taxes would one day no longer hold the appeal it once did. 

Around the same time that I was rolling in my $80, I started my first blog, which slowly began to garner outside attention and lead to job offers at indie magazines and websites. Over the following eight years, I accumulated more bylines while working a string of service industry jobs — at a shoe store, a candy store, a cafe — though never earned enough to make a significant boost in my annual income. But a few years ago, at the age of 24, I was getting enough offers for regular writing work that I could afford to scale back dramatically at my day job, then at a bookstore. 

On my first day as an official writer, I applied for an HST number because I heard you needed one of those to be taken seriously as a small business owner. And was I not now my own business? I didn’t understand what an HST number was, only that it was necessary if one was earning more than $30,000 a year (which I was, ahem, not), or what it meant to “collect HST” on invoices. I assumed that having an HST number was a symbolic measure, a bit of personal trivia to drop at parties, like knowing what your moon sign was. I kept track of all my assignments in a colour-coded Google Doc, and patted myself on the back for finally figuring out a career that I'd been warned would be tough. 

And then tax time rolled around. 

I assumed that having an HST number was a symbolic measure, a bit of personal trivia to drop at parties, like knowing what your moon sign was

As I had done in previous years, I filed my own taxes using a free online program. I approached this like I would any tedious chore, knowing that even though it was time-consuming, it would at least lead to another nice cheque in the mail. This time, however, my taxes took hours to do. I had expenses I accrued while researching stories to track and receipts for office supplies to deduct, as well as cryptic fields to fill out that never gave me trouble before. When I finished, it said I owed the government a few hundred dollars. That didn’t seem right. So, I did the whole thing again. It was the final day income tax was due so with no time to spare, I just guessed at what to enter where, until the computer spat out a number I would be getting as a return. Satisfied, I filed and went to bed. 

Several months later letters from the CRA started appearing in the mail, questioning certain sections I’d filled out on my taxes, requesting my HST payments and warning me that I would have to pay interest if I didn’t do so soon. I panicked. This is it, I thought. This is how they got Capone. I’m gonna go to Alcatraz. I hid the envelopes in my desk drawer but they just kept coming. It was a friend who recommended an accountant to me who specializes with artists and freelancers. I made an appointment with Sunny and showed up with a box containing all my ignored envelopes, past invoices, contracts, paperwork and any other scrap of relevant information I could find. Her office was filled with impressive-looking math books as well as knick knacks, toys, a ukulele and a fish tank. She had a soothing presence, and I was worried she’d take one look at the mess I had found myself in and kick me out. Instead, Sunny assured me I was not going to go to Alcatraz, and got to work untangling my mess from the previous 18 months. As she did so, she walked me through the process so that I wouldn’t make the same mistake again. 

This is it. This is how they got Capone. I’m gonna go to Alcatraz

Once she calculated what I owed, I had a good cry, then made a plan to start paying it back. Yes, it was stressful learning that I had needlessly put myself in debt, but the anxiety-inducing drawers filled with mysterious envelopes had now morphed into a tangible number that I knew what to do with. I started collecting HST on my invoices, and set up a direct withdrawal system from my bank account to put money aside throughout the year. I returned to Sunny the following spring, and paid her to do my taxes — a worthwhile investment. 

I am still in many ways much a mess when it comes to money. Being a freelance writer means instability, and I actually have worked a few day jobs over the past few years to supplement my income when I just wasn’t getting enough well-paying assignments. But learning to invest in an accountant and to trust an expert meant that I was taking my career seriously, which took the anxiety and uncertainty out of tax time. No, I don’t get a return when I file, but I do get to call myself a professional writer. That seems like a pretty good tradeoff. 

Illustration by Janice Wu