My Path to Creative Entrepreneurship

I was that kid in elementary and high school who sort of faded in to the background; if with a slight rebellious edge. My grades were pretty average, I wasn’t typically quick to raise my hand (I was kind of shy), and it felt like my friends all stood out for one reason or another a lot more than I did.

The one place I always felt seen, though, was in art class. Even if I wasn’t the most academically ambitious in high school, I rolled through my art classes with ease. I had an intangible “creative eye”, or simply a passion for drawing and image-making in particular. This much I know for sure: when creating something original, I would lose myself in the process in the best sort of way. I know other artists will relate to this feeling.

When it came time to decide what to do with my life beyond high school, the obvious choice was a creative career. So, I applied to two programs: Graphic Design at York/Sheridan, and General Arts at OCAD. Both programs meant moving away from home in Ottawa, to a new city (Toronto), and in the end, I chose the Design program – even with nary a clue on how to use the Adobe software, on gut instinct, design just felt right.

University was an interesting experience; from a design perspective I was not great in the first couple of years; for personal reasons among others – but by third year I hit my stride. Not only was I just getting by, but I was actually excelling (and surprising myself). By fourth year, even my peers, who at one time surely thought I wasn’t cut out for the extreme challenge of our prestigious program, were giving me props. In the back of my head I remember thinking, my parents didn’t help me out all these years for nothing – let’s try to get some good portfolio pieces out of this and make it happen.

While I was finishing my final credit (long story – but ironically my last credit to complete my degree was actually a drawing class at OCAD), I got a part-time junior design job at a start up, run by two freshly minted business partners. This felt very cool at the time, even though it was only part-time (by the way, that company has grown a lot since, and continues to be extremely successful). Simultaneously, I was working at RedBull Canada, cruising around the GTA as a RedBull Wings Team representative. I was also serving beer at festivals. It was a great combination of fun creative things that summer. I ended up deciding to move home to Ottawa in the fall, but almost immediately found myself applying to Toronto jobs again. I remember sitting at an Ottawa Starbucks and coming across one job in particular – a design internship at the Toronto Blue Jays – and what do you know, as fast as I left, I was moving back for what ended up being the most incredible job opportunity to me at the time.

I lived in a tiny (admittedly decrepit) apartment on the downtown west side of Toronto, making 13 dollars an hour, and honestly – truly loving life. I’d pinch myself as I walked to work every day – the CN Tower in the near distance (and right beside my Jays office at Rogers Centre). The city represented a thousand possibilities for the future, and this was just the beginning! I had an amazing boss at the Jays who nurtured my (very green at the time) design skill set, never making me feel like as much of a noob as I was. Not only that – that year, the Blue Jays made a historic Post-Season run towards the World Series (queue, Bautista’s Bat Flip). My internship got extended into winter.

Ultimately, my Internship did come to its natural end, and I’d already applied to a job in Ottawa – another sports gig with The Ottawa Senators. This time, for a full-time graphic design position.

Working there for a year, I met so many incredible people; and it gave me a new perspective on what I wanted next – I was ready to move on from the sports world, and try my hand at an agency. Setting my sights on that new goal, I applied and got my next role at an Ottawa-based digital agency. This new agency was a fun experience – another instance where I had a great Creative Director who respected where I was at in my career, and genuinely cared to try to make me a better designer.

After being there for another year, the next agency job I took was absolutely incredible (CT) – I had a close friend working there at the time, and the projects felt more aligned with what I was interested in, so I took the job when it was offered. I was there for three years, working on all sorts of colourful and exciting projects with top talent in Ottawa, and making life-long friends while at it. 

By year three, however, the pandemic had caused a paradigm shift in my thinking – I was working from home, and oddly being more okay with the #WFHlife than I ever thought I would be, and I’d also taken on quite a bit of freelance that was escalating to a place where I felt there was a decision to be made, and I knew deep down what I wanted to do.

That artsy kid who faded in to the background for many of her formative years, plucked up her confidence, and somehow took the leap in to the relative unknown – leaving a stable job by choice for the realm of entrepreneurship. Neither of my parents are entrepreneurs, and were not overly encouraging of this decision at first. Although I had some decent leads for freelance in place, those only went so far. It was scary and emotional, but the little voice in my head (along with my exceedingly supportive partner, who is also an entrepreneur) encouraged me – and the moment I made the decision, I felt empowered and ready to go.

That decision was just shy of two years ago as I write this (November 2022). The past couple of years have been some of the most professionally challenging and utterly intimidating years of my life. They have also felt the most rewarding and meaningful to me. I’ve realized that autonomy and creative freedom are huge values of mine – I actually do love the business side of things, and taking on clients who I align with on a human level, and whom I can work with one-on-one to create with and for, is what I absolutely love to do. 

So, why the intro? To kick off this blog/journal in an authentic way, I thought why not explain the up-til-now. Being eight years out from my post-secondary days, I’ve learned a thing or two along the way, and I’m hoping this blog/journal can offer up helpful little nuggets to fellow designers, biz owners, and creative folks, while also being an extension of the resources I offer to those I work with moving forward.

All of that to say – entrepreneurship is not for everyone, but for those whom it is right, I strongly believe there is o better path, even with all the trials, tribulations and burnout that comes with it (I know, I’m really selling it). Hopefully, if you’ve made it this far, you’ve gotten something out of this little story.

What’s your story? Let me know in the comments – and I hope to catch ya next time.

–CN.