Alyssa Garrison; Toronto;
Let’s say we’ve just met at a cocktail party. How would you describe, in a nutshell, what you do?
I’m the founder of , a lifestyle blog that celebrates the everyday with colour, sparkle and a heavy dose of fun. RAOP also includes a small boutique agency side, and an .
Where did you go to school and what did you study?
I went to Ryerson University for journalism. I wanted to be a magazine editor when I “grew up.”
What was your first paying gig out of school? (In your field, or not.)
Writing for the now defunct XO Vain (RIP).
What was your BIG break? How did you land it?
I was featured on in the spring of 2014 and that was a huge moment for me—for half the day I couldn’t place where all the new traffic and followers were coming from!
Describe the moment in which you first realized, I think this is actually going to work out?
I was working at an agency doing digital marketing and one day I sat down and tallied my income, and realized staying in my full-time job was actually costing me money. It was a big “ah-ha” moment and a couple weeks later I quit the agency—I’ve been working for myself ever since.
What would you say has been your biggest failure or shortcoming, career-wise, to date? How did you bounce back?
I think my impulse is to trust too much when people haven’t earned it. It’s led to a lot of big disappointments. I’m slowly learning how to play hardball and think like a business owner—not a friend—but it certainly doesn’t come naturally to me.
Name one piece of career advice you always give.
Nothing big can happen without a big risk, and I’ve always felt that it’s better to try and fail then to stay stagnant. Push yourself, get out of your comfort zone, and do the stupid thing sometimes—you never know where you’ll end up.
What’s the worst career advice you’ve ever gotten?
Someone I admire very much loves to say, “Say yes to everything!” and though it’s not bad advice per se, I think I took it too much to heart. Right now I’m focusing on the art of saying no, otherwise I’ll run myself and my team into the ground.
Did you deal with barriers in your field because you are a woman? If so, what were they?
Luckily my field is very much dominated by women, so I have the privilege of interacting mainly with other girl bosses. That said, I think it’s easy for that kind of atmosphere to breed a bit of competition and cliquishness. The biggest challenge I’ve identified is getting everyone to work together, not against one another. We all have a responsibility to make sure we’re supporting one another and recognizing we’re each doing something unique.
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 feel extremely privileged to have a very fair income from just working for myself. I do my best to employ other women and pay them fairly as well, which is such a special position to be in!
What’s the worst stereotype you’ve heard about millennials at work?
The other day my mom said something about how much more complicated life is now that everyone is comparing themselves to one another online, and how much happier people were in their 20s when she was my age. I guess millennials are to blame for the shift by constantly publishing only their “best lives” and “doing it for the ‘gram.” Maybe we need to simplify and just… live our lives.
Photographer, Nathan Cyprys; stylist, Corey Ng, P1M; hair, Cia Mandarello, P1M; makeup: Vanessa Jarman, P1M; dress, Milly at Holt Renfrew.