Haley Cullingham; Toronto;
Let’s say we’ve just met at a cocktail party. How would you describe, in a nutshell, what you do?
I’m an editor at Penguin Random House Canada, working primarily on , a website that runs great, unexpected writing: everything from investigative long-form reporting to fiction, memoir and interviews. Today I’m editing pieces about the complications of surrogacy arrangements, , and .
Where did you go to school and what did you study?
I started out at the University of British Columbia in a general fine arts program, but before I chose a major there, I decided to move back to Toronto and transfer to Ryerson’s journalism program, where I graduated in the magazine stream. I’m currently doing a part-time creative writing master’s in fine arts through UBC.
What was your first paying gig out of school? (In your field, or not.)
Working as an editor at a female-run arts and culture website. While I was still in school, I sent a bunch of writing about music and road trips to the editor, and she gave me a paid internship for a summer, which I did while working at a call centre in the evenings, and then she hired me part-time while I was finishing my degree and brought me on full-time once I graduated. Having that experience—editing, managing writers, navigating press days—before I graduated was a huge advantage. Between that, and freelance writing, editing and fact-checking, I was able to make a living income directly out of school.
What was your BIG break? How did you land it?
The year I graduated, I applied to be the associate editor at , a not-for-profit magazine based in Montreal. It was exactly the kind of work I wanted to be doing—editing long-form magazine writing. It felt like a long shot, and it meant I would have to move and work for an honorarium. But I got it and was eventually promoted to editor-in-chief.
Describe the moment in which you first realized, I think this is actually going to work out?
I don’t think there was one particular a-ha moment for me. It was an accumulation of small victories, moments of real excitement about what I was doing, support from mentors who encouraged me to keep working, and appreciation from writers that made me feel as though our work together had helped make their piece stronger.
I think unfortunately, working in media, you’re always worried that your fortunes are about to dramatically shift. But at the end of 2015, when I was working as both an editor at Hazlitt and finishing up as editor-in-chief of Maisonneuve, I remember feeling like, even if I never got to work as an editor again, I’d been able to work on some really wonderful things and I was proud of that.
What would you say has been your biggest failure or shortcoming, career-wise, to date? How did you bounce back?
When I was early in my career, I would rely on other people’s opinions more than my own instincts, and that led me to develop insecurities that, in retrospect, just slowed me down. Advice is always useful, but I’ve learned to factor it in, not let it override my own opinion, and now I’m more careful about whose voice I allow in my head.
Name one piece of career advice you always give.
Prioritize your mental and physical health. Do allow this advice to override your own opinion.
What’s the worst career advice you’ve ever gotten?
Honestly, even terrible advice is good, because your reaction to it tells you something. But I’ve had a lot of people encourage me to stay in work or academic situations for far longer than I should have. In the words of a lady who read my tarot cards in New Orleans once: deep down, you always know when it’s time to leave.
Did you deal with barriers in your field because you are a woman? If so, what were they?
As a young female editor giving people direct feedback about their writing, there were a lot of male writers who didn’t respect my authority. They tend to be nicer to you after you edit their work and it wins an award. I heard stories, countless stories, of male writers and editors dehumanizing women in all sorts of ways. I’ve come up with a group of women who are very vocal about and aware of the sexism built into our industry and doing the thankless and brave day-to-day work of fighting for their own rights and the rights of others. Having that community and support makes it easier to deal with sexism. But I’ve also been lucky in another way—I’ve only ever worked at publications where feminism is part of the magazine’s DNA, and that is incredibly rare. Hopefully, it won’t be rare forever.
I’m also white, and cisgender, and from a middle-class background—things that mean I have benefitted from a significant degree of privilege in this industry. I’ve learned a lot from the women around me who are leading all of us in the crucial push for more truly representative mastheads and bylines. My hope is that soon, the men who wouldn’t want to credit an editor because she’s a woman will have gone extinct, and everyone will be publishing work that actually reflects the people who live here.
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?
I am, but it took many years of working two or three jobs to get here. I’m so lucky to have a full-time job with benefits in this industry, and I’m grateful for it every day. I still freelance, though, because I have debt I’m paying off from the years when I was working a few lower-paying jobs at once.
What’s the worst stereotype you’ve heard about millennials at work?
That’s not something I’ve really had to deal with, somehow, which is nice.