How I Made It

Robyn Doolittle, Investigative Reporter

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

Robyn Doolittle headshot

Robyn Doolittle; Toronto; @robyndoolittle

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

I usually try not to, because it will inevitably lead to someone asking me about the Rob Ford crack video! But if pressed I would say: I am a reporter with the Globe and Mail’s investigative team.

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

I went to Ryerson University and studied journalism.

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

Don’t hate me, but I was working full-time at the Toronto Star as soon as I was done university.

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

I suppose that would be landing an internship with the Toronto Star’s radio room—students listen to police scanners and write little news stories—before my fourth year of university. I got the summer reporting spot the following year, then a year-long contract and finally a full-time job. But I suppose backing up even further, the Star only hired me because I’d spent the previous summer hustling by butt off as a reporter at a daily newspaper near my hometown, the Sarnia Observer. I left that experience with thick portfolio of published work.

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

As a summer reporting intern with the Star, I was sent to Chicago for the end of the Conrad Black trial with one assignment: get a juror to talk about the verdict. (In the United States, unlike in Canada, jurors can talk about cases afterwards.) I spent about five hours waiting on the woman’s front porch, but I was the only journalist—American or Canadian—to get an interview. That was a turning point for my career for sure. [Robyn went on to report on the downfall of former Toronto mayor Rob Ford for the Star, and also wrote a book about him.]

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

At the peak of the Rob Ford investigation, I remember thinking: Oh man, when this is over, how am I going to follow this? And it was as tough as I imagined it would be. In 2014, I joined the Globe and Mail’s investigative team and for that first year, I struggled a lot mentally—both with making the transition from daily news reporting to investigative work and also with all the self-imposed pressure I felt after the Ford story.  But the paper really encouraged me to take my time and pick the right project. So I did. The result was a 20-month investigation into how Canadian police services handle sex assault cases. And I’ve never been more proud of a piece of work. The series is creating real change across the system in every corner of the country.

Name one piece of career advice you always give.

The number one piece of advice I give to people is: don’t be a jerk. It never serves you well in the long run—or short-term for that matter.

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

When I was younger, there seemed to be this expectation that you had to be cutthroat to get ahead. I have just always found that being yourself and not acting like a jerk works a hell of a lot better.

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

The best examples are the times when I’ve worked with male colleagues on a story. We are doing the exact same reporting, but I’ll often hear myself being described as “aggressive” or “ambitious” or “pushy.” I have never in my entire career heard a male colleague being described in any of those ways.

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?

Considering the state of the newspaper industry these days, I feel incredibly lucky to be where I am at the Globe. Full-time reporting jobs at big daily newspapers are not easy to come by these days.

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

Apart from the occasional good-natured ribbing about social media habits, I think I’m in a pretty millennial-friendly work place. Of course I’ve heard the complaint from society in general that millennials are lazy, but from what I’ve seen, they’re often among the hardest working, because they have the most to prove and there aren’t a lot of jobs.

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