How I Made It

DeAnne Smith, Comedian

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

DeAnne Smith headshot

(Photo: Scott Reynolds)

DeAnne Smith; Toronto; @deanne_smith

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

I’m a stand-up comedian. My whole life is jokes!

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

I went to a small liberal arts college called Alfred University. I studied English, gender studies and writing. The perfect combo for comedy.

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

I worked as an assistant editor for a photography magazine. It was fun, but the cubicle life is not for me.

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

A few moments stand out so far. Having Roseanne Barr tell me I’m funny and pass me on to the next round in Last Comic Standing was amazing, as was doing comedy on the Late Late Show. I’m not even sure how I landed either of those gigs. For both of them, I got emails out of the blue. Clearly someone in the industry had seen what I do and liked it.

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

Two years in, when I started paying all my bills from doing comedy. I never looked back.

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

One thing I struggle with is having the confidence to push myself forward. I often think I need to have everything perfect before I move on to the “next level,” whatever that may be. But then I tell myself that’s bullshit, and I do the things anyway!

Name one piece of career advice you always give.

Take all the opportunities that come your way! Say yes to as much as you can, because you never know where it might lead.

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

Anything bitter, older men who haven’t really succeeded at comedy have tried to tell me. “It takes 10 years to build a good 45 minutes.” “You’ve got to go out drinking with the club owner.” Nah.

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

I’m sure I do! Comedy is still such a boys’ club. I’ve always forged my own way, though, so while I’m sure there are some barriers there, I don’t see them. I’m too busy moving in another direction.

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

Jokes are my whole hustle, and the income varies. Some gigs pay astonishingly well, others not so much, and some don’t pay at all.

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

There are so many! One is that they don’t work hard enough and don’t pay attention to little details, like fact-checking.

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