My brother’s computer was the first computer I got to use. At the time, video games were rudimentary but oh, so solid. When I inherited his computer, the colours of Commander Keen burned my retinas neon as I clocked in the hours perfecting the perfect pogo jump.
At some point I was introduced to Asianavenue, Neopets, Photoshop, interest-specific chat rooms and forums on ezboard. That was the hook and I was married to the internet from then on. At 13, I started making my first websites: a profile on AA and a geocities website proudly declaring my favourite things.
As I went through high school, I had convinced myself I wanted to study Computer Animation. After going through a preliminary portfolio course I realized that I had no interest in drawing other people’s creations. So, I enrolled in Graphic Design instead because frankly, what else was I going to do?
At 19 I was released from what I considered to be prison (being an adult was very appealing to me). I had some websites I had created, about five years in the workforce, a useless ability to draw Bart Simpson and Ren & Stimpy from memory, and a vague sense of direction.
My first (career) job was found through my hobby at the time: photography. I rented a photo studio and convinced the owner that he needed me as an assistant. This would start my life-long career working directly for entrepreneurs.
I helped him with his websites, his rental clients and whatever else he needed. It was a part-time position and I spent the rest of my spare time shooting for local bands and developing a better understanding of the local commercial fashion industry. I learned the ins-and-outs of studio and on-location lighting and got to meet some really cool and ridiculously good-looking people. Eventually I realized it wasn’t the career I wanted so I jumped on Craigslist and found a job with another entrepreneur helping to grow her branding agency.
After about a year of working with her, I got an itch to try something substantial so I wrote a business plan and opened up a community photography rental space in a fancy brick-walled loft. I worked full-time at the branding agency and full-time at my rental studio. I hustled for clients, built a booking system online, and learned basic marketing to get my business off the ground. Within a month I had a steady stream of clients and workshops running. I was working 60-80 hours a week but it never felt like a sacrifice. I closed the studio after a year and went back to focus on my work on the branding agency.
These three years were the most influential years of my career. I learned how to work with clients, how fast I could produce, how to set and work under deadlines, how important morale was, how to manage someone (didn’t do this well at the time), and how to build responsive websites from scratch. We launched some of the first responsive websites in Canada at a time when the agencies around us were still catching up.
Then I quit. I went to Barcelona and ate ham and cheese croissants every morning and wondered why everyone wasn’t awake yet at 9AM. I wanted to work in product but there were not many opportunities in Toronto at the time and I had a portfolio of agency product work. I interviewed for a few companies in San Francisco but no one took the bait. After three weeks in Barcelona and some lazy searching, I was offered a position at a start-up in Toronto for another entrepreneur and I took it. I’d never been good at being unemployed.
I hated the start-up; the working culture was awful. Three months in, someone found me on Twitter and we had a long conversation about my job over lots of cocktails.
Three months later I had had enough. I sent a one-sentence resignation email and sent a subsequent two emails to a recruiter and the original someone telling them I needed a new home. Four job offers on the table in two weeks and I chose Jet Cooper. Then six months later, Satish and Verne pulled us all into the ping pong room and told us we had been acquired by Shopify. Now I work for entrepreneurs, again, except I answer to about 243,000 of them.
I have been asked quite a few times, “How did you get into Product Design?” I think they ask because they’re looking for a magic answer or for me to say something which would give them some direction. I am telling this story because it’s not linear.
I followed my gut and I did what I could. When I liked something, I did it again. If I didn’t like it, I quit. This has guided nearly all of my decisions, career-related or not. I could use this to explain away my career but I won’t.
The truth is my career has been as deliberate as it’s been undeliberate. A career is something you only see looking backwards and if you had pointed me to someone who had planned out their entire life at the start of the trail, I probably would not have wanted to follow in their footsteps anyway. It’s just not any fun knowing what’s around the corner.
Regardless of what path you choose, you’ll learn and it’ll feel like you chose it. Even then, I doubt you would fully believe you chose it. Robert Frost succinctly captures this feeling with the singular word, “sigh” in the following prose from his famously misunderstood poem The Road Not Taken,
I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.
Chase growth. That’s just about the only path that matters.