Hayley Wright, Illustrator and Skate Deck Designer

FLARE #HowIMadeIt celebrates 100+ talented, ambitious and driven Canadian women with cool jobs. Want what Hayley has? Here’s how she did it

Hayley Wright HeadshotHayley Wright; Edmonton; 


Let’s say we’ve just met at a cocktail party. How would you describe, in a nutshell, what you do?

I’d buy you a drink and tell you about how I draw portraits for a living while also creating custom skateboard and longboard decks.

Where did you go to school and what did you study?

I did my bachelor of fine arts at the University of British Columbia, in Kelowna, B.C. Then I studied fashion marketing and merchandising at the Vancouver College of Art and Design.

What was your first paying gig out of school? (In your field, or not.)

My first “real” job after was as a divisional manager at . This experience gave me invaluable business skills that have really helped me succeed today. As much as I loved the job, though, I knew I had to take what I learned and pursue my career as an artist.

What was your BIG break? How did you land it?

In the spring of 2015 I was ed by Fido to help them with their #GetCurious campaign. They had chosen an artist from each major city across Canada, and I was invited to create a live-drawing on their stage at in Toronto later that summer. It was the first time I felt relevant and important—like my artwork mattered and could be used to encourage others. I landed this opportunity entirely through word-of-mouth: an Instagram follower of mine passed along my name.

Describe the moment in which you first realized, I think this is actually going to work out?

Every once in a while, I wonder if it would be easier to find a “real” job and just leave my art as a hobby, but then something amazing always happens! My first big a-ha moment came during the 2016 holiday season. It was shortly after I began , and I really wasn’t sure how big it would become, as custom skateboards are such a niche market. But by the beginning of November, my waitlist was already six weeks long.

What would you say has been your biggest failure or shortcoming, career-wise, to date? How did you bounce back?

If I could go back and do one thing differently, I would have focused earlier on learning the business aspect of the job. Being a full-time artist also means you have to be a marketer, social media magician, accountant, customer service representative, photographer, web developer and everything else.

Name one piece of career advice you always give.

“Don’t let yourself get in your own way.” I stumbled across this little quote one day and, at the risk of sounding dramatic, it honestly changed my whole life. I realized how many times a day our brains can try to keep us away from success through procrastination and self-doubt.

What’s the worst career advice you’ve ever gotten?

“Give yourself six months to make this work, and then find a new career path.” It can take years—not months—to see any kind of success in a small business.

Did you deal with barriers in your field because you are a woman? If so, what were they?

Creating custom skateboards in a field that is primarily male-dominated was intimidating to me at first. I was worried that I wouldn’t be taken seriously or that my work wouldn’t be well-received. It was important to me to move past these feelings and just focus on creating awesome work. There will be times when I face criticism, but I am ready to tackle them because I believe in my work.

Are you making a fair income for your work? Why or why not? Do you have a side hustle/day job for extra cash? If so, what is it?

I do make a fair income from the work that I create, but my business isn’t yet big enough to focus on full-time. I create tasty lattes on weekday mornings and sell vintage dresses online for extra cash.

What’s the worst stereotype you’ve heard about millennials at work?

I dislike when millennials are thought of as lazy and entitled just because we are no longer content clocking hours at a 9-to-5, and instead want to create our own paths. This is a time when you can do almost any job imaginable, but it takes a ton of hard work and motivation to get there.

Photographer, Nathan Cyprys; stylist, Corey Ng, P1M; hair, Cia Mandarello, P1M; makeup: Vanessa Jarman, P1M; jacket, Kenzo at Holt Renfrew.

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