THE ELLE GUIDE

How to channel your inner Tess from Working Girl— without any of the drama.

MALGOSIA GREEN MOVED across the country from Toronto to Vancouver to sign on as CEO of the massive dating site Plenty of Fish last year. She was 39 years old and had launched several profitable start-ups but had never worked at a public company. Suddenly, she was the head of a website that had over 150 million users. “The biggest trend in my career is that I take a lot of risks,” says Green. “I’ve made a lot of moves that didn’t seem linear, and sometimes those risks blew up in my face, but overall it has accelerated my learning and career progression.”

Is the adage “Fail fast, fail often” true?

“It’s best not to fail, to be honest. But sometimes you will, so if you have a high level of self-awareness and a lot of humility, you will learn from your mistakes more quickly. Leadership is so nuanced. As a leader, you might not actually know that you’re failing unless you’re humble enough to get feedback and be self-reflective.”

But does being humble make you seem weak?

“I see admitting you don’t know something as a sign of strength. It takes real courage—more so than putting up a front. Let’s admit it: When you are in a new position, you don’t know what you’re doing, so it’s okay to have doubts. There have been so many times when I was terrified of doing something but did it anyway. Sometimes it hasn’t worked out, but for the most part it has.”

Have you always been comfortable with risk?

“I’d say I’m comfortable with pushing myself. I’m not competitive with other people, but I’m very competitive with myself. I love the opportunity to work with people who are more talented or skilled than I am—that’s when I feel most alive. I always try to be in a room where I’m not number one, where I’m near the bottom, because I know I’ll level up.”

What was your first day as CEO like?

“It was terrifying. I was commuting back and forth between Toronto and Vancouver for the first few months, so I woke up alone in a hotel room that morning and got dressed, and I felt like I was just going through the motions, almost like I did on my wedding day. It took me at least six months—probably closer to a year—before I felt like I had a mastery of the pieces at play.”

How can you tell the difference between nerves and your instincts telling you you’re making the wrong decision?

“Some decisions you can’t make rationally—you should go with your gut when, say, you’re deciding who to marry—but with decisions around your career, you should be able to weigh the pros and cons. Take a step back and rationally think things through. If you go through the logical process of evaluating your decision and it makes sense but you’re still scared, that’s okay.”

How do you know when it’s time to make a move?

“There was a moment early in my career, when I was in my mid-20s, when I made a decision that was very reactive. Now every time I feel frustrated, I take a step back and remind myself that there are challenges everywhere you go and that taking the time to overcome those obstacles is way more satisfying than just jumping over to somewhere else that seems to have a clearer path. Working to complete something and getting to a place where you’ve made a mark before jumping on to the next thing is important. I see a lot of people today moving from job to job every other year, and I question whether that’s sufficient to really make your mark.”