Sarah Robb O’Hagan, CEO of FlyWheel Sports, has served in executive roles at Nike, Gatorade, and Equinox, and is the author of ExtremeYou. She recently joined Ann Shoket, former editor-in-chief of Seventeen and author of The Big Life, for a Heleo Conversation on why getting your career started is more important than immediately finding the perfect job. They discuss why “having it all” is overrated and why being uncomfortable means you’re on the right track.
This conversation has been edited and condensed. To view the full conversation, click the video below.
Ann: Frankly, I’m terrified by this idea of being extremely me all the time. It sounds like such a hard thing to do. What’s the number one secret to getting extremely you?
Sarah: The misconception is that “being extreme” is like running hard, pushing hard, like extreme sports. It’s more a term for deeply knowing who you are, having experienced things in your life, good and bad, that make you go, “This is where I shine, where I thrive and where I’m going to place myself, my time, and my effort, so that I’m having a good time and succeeding with the best version of me that I can be.”
Ann: When did you first learn that thing that you’re awesome at?
Sarah: By sucking at a lot of things.
Having spent most of my career in the sports industry, everyone assumes I must have been a world class athlete. But I never made the top team in field hockey, never won a medal in any sport that I was part of. I sucked at a lot of things, but it didn’t mean that by participating and pushing that I didn’t develop a passion for them. I realized I might not be amazing or a world champion, but the experience of playing on a team and being physical helped me to understand what I loved doing. Look where I ended up with my career—it all goes back to spending time discovering yourself.
You are what I would call an extremer, because you are doing something that you are very passionate about. You have an incredible amount of skills that have brought you to this moment. Where was it in your life that you discovered where you thrived?
Ann: I have always been interested in this moment in your life when you’re becoming who you’re meant to be: you’re pure potential. There’s no rules, you get to imagine the way the world will work for you. Even if you end up struggling down the road and it doesn’t work out that way, it feels possible.
I started my career as a reporter at The American Lawyer magazine, which was not my idea of a dream job. I went from The American Lawyer to a teen news magazine where I wrote about legal issues for teens, like curfew and drinking. A girl who escaped from a cult was a big story. And I was like, “I sort of love it.” There’s irreverence, a real energy, and momentum, and I kept following that thread. From there, I went to launch Cosmo Girl, and I stayed at Cosmo Girl for eight years because we were having deep, important conversations. When I got to Seventeen, it was my chance to shape that conversation about what young women need to know to become as amazing as they possibly can be in the world.
Sarah: One of the misconceptions I come across when I speak to young women and men is that they feel so much pressure to make the right career decision, to get the right job. That first job that you took, even though it wasn’t awesome and wasn’t perfect for you, is there something out of it that now informs where you ended up?
“Get a job, any job. It doesn’t matter, just get started. You need to learn how the world works, you need to learn how an office works. And you can learn that anywhere.”
Ann: 100%. This is something I say all the time: get a job, any job. It doesn’t matter, just get started. You need to learn how the world works, you need to learn how an office works. You need to understand the weird secret handshakes and be nice to the receptionist, or your lunch will never get delivered. And you can learn that anywhere.
The boss at The American Lawyer was this cigar-chomping yeller. He was brilliant and knew how to build a company. There was a magazine, newspapers, an online service, and real world events. He was putting together all of the pieces. That idea is my trademark in business. I didn’t know when I was 22 years old that I was learning these things, but that became my trademark. I might not have learned that had I been somewhere more traditional.
Sarah: Who would have thought when you’re the CEO of a fitness company that you suddenly go, “Thank God I worked clearing mini bars in a fucking hotel”? All of those experiences, twenty years later, you tap into them. We put so much pressure on young people to get these amazing, perfect jobs and have perfect resumes. Don’t worry.
Ann: But where did that come from for you? Who told you not to worry?
Sarah: I come from New Zealand, the land of fifty million sheep. The expectations are not very high. There wasn’t this pressure to be ahead of other people very quickly.
Ann: Is that better?
Sarah: It was very freeing. I don’t [think] any of us felt we weren’t doing well. We were having a good time. What’s wrong with that? To your point, whatever the job is, you are learning skills. You’re learning how to be in the world. There’s nothing wrong with that.
Ann: When you were 16, what did you imagine your life would be like?
Sarah: I don’t even think that my vision could have imagined getting outside the country. It never would have occurred to me that I would end up in another country raising American children. I was limited by the perspective of the world I was in. I can remember saying, “But I want to be a radio DJ.” In those days it was like, “No, go down a very vocational path. That’s far safer.” Now those same passions have come full circle to the other side.
When you are young, if you over-listen to the people who are trying to give great advice—to give you a safe, steady, secure future—that’s not what makes you fall in love with what opportunity is in front of you.
Ann: That idea that you just described is what the big life is: not what somebody else says you should do, not having it all. Do you know anybody that has it all and who is supremely happy?
Sarah: What is “it all”?
Ann: It’s the big job, the hot husband, the adoring children—it’s what somebody else says you should have in the order that they say you should have it. It’s this pressure. You sit there paralyzed by this pressure because you’re like, “Well, that’s not what I want to do. I want a big job. But I want that big job to be being the DJ at a radio station. I don’t know if I want to get married. Maybe we will have children and maybe we won’t.”
“Having it all” eliminates all of the possibilities for the way your life could go, that idea that you had when you were 16 years old in New Zealand of wanting something that wasn’t there. That’s actually phenomenally hard—to look outside your window and imagine a world that’s bigger than anything you can see.
“When you are young, if you over-listen to the people who are trying to give great advice—to give you a safe, steady, secure future—that’s not what makes you fall in love with what opportunity is in front of you.”
Sarah: Yeah, I was ambitious. I didn’t exactly know for what. But I knew I wanted to be successful and I didn’t want to stay put. My entire career strategy when I left college was to get a job with the airlines because that will fly me out of the country. That was it. And it worked!
After I had been relocated and living in the States for maybe four years, all of the women my age—I was in my late twenties—were like, “The clock is ticking. Better move home.” I felt this pressure to do what was expected. Then, I remember a friend saying to me, “Why? You’re having a great time where you are. Just keep following it. What’s wrong with that?” And I’m like, “Actually, you’re right.”
Ann: You didn’t know that you were going to stay?
Sarah: No. Honestly, until three or four years ago, I kept telling them, “Yeah, we’re moving.”
Ann: So what took you from travel to sports?
Sarah: I desperately wanted to work for Nike. I had grown up on that brand. I was a marketing executive, I’d done six years in the airlines, I finished up at Virgin Atlantic, and was like, “Of course Nike is going to hire me. I’m awesome! Why wouldn’t they?” In those days, headhunters or recruiters would say, “You’re an airline person.” That’s another trap people fall into: the system is designed to make you fit in. You have to bust out and go around. Resist being pigeonholed.
I interviewed several times. I got rejected several times. Then, eventually—right role, right time—it worked out. But I always tell people, “Don’t take no for an answer. It might just be the timing is wrong.”
Ann: It might be the wrong recruiter. It might be the wrong person and the wrong role. People move around.
Although, one of the young women that I interviewed for my book was so set on one job. I kept trying to say, “What about this job in another industry?” She was just set on this job. She didn’t get it, and then she was up for it again, and she didn’t get it again. So that was it. She started her own business.
If you’re not getting the job, you have to think about what that job means to you. You can’t get set on one path. Maybe she wasn’t there yet. Maybe she needed a little more space. But what does that dream job mean, and how do you get that feeling?
Because a lot of young women say to me, “I don’t know what I want to be, but I know it needs to be big.” We’re chasing big, meaningful. That’s the important thing. That’s your North star.
Sarah: To that point, one of the things I talk a lot about is failure. We build this crazy culture around perfection and we’re all awesome on Instagram. We don’t ever show when anything goes wrong. The fact is, all of the people I interviewed for my book who were top-of-the-game in their chosen profession, every one of them could point to something that had gone drastically wrong which pivoted them to where they work. Did you have any experiences like that?
Ann: I don’t believe in failure. I know that everybody loves to talk about failure, it’s everybody’s TED talk these days: “Ways I fail,” “How to fail,” “Big fail.” I get it. But I don’t believe it. Because I think if you’re not risking things every day then you’re not working hard enough, trying hard enough, or pushing yourself hard enough. I never see things as a failure. “That happened. That sucks. Let’s figure out how to learn from that and move on.”
“The system is designed to make you fit in. You have to bust out and go around. Resist being pigeonholed.”
The story that I have only recently become comfortable telling is that I was up to bat to be editor-in-chief of a magazine twice before I landed the job.
The first time, I was just not ready. But I knew someday I would be ready, so raising my hand in that moment was really important. I was pitching a brand new idea, a good idea. It just wasn’t in the budget. But that let my bosses know that I was interested in something bigger. I was a good, solid, mid-level senior person. But I needed to hop out of the crowd.
The second time I was up to bat, I wasn’t as nervous. I was more ready. I knew how to make a pitch. I didn’t get that job either, but not because my idea wasn’t good. It wasn’t the right time; somebody else was ahead of me in line. But the next time I walked into the room and was like, “Okay, I’m ready now.”
Had I not tried for those other gigs, I wouldn’t have been prepared, I wouldn’t have been polished. I would have been nervous, I would have not known how the meeting would go. All of that matters. I don’t see it as failure.
Sarah: If you can live that way, outside of your comfort zone, then you’re going to get a lot further than if you’re just sitting there going, “I’m not willing to take the risk because I might fail.”
Ann: I call it putting rocks in your shoes. You have to be uncomfortable. I think it’s part of living in New York. If I lived somewhere like San Diego, it would be harder to hustle, because it’s so beautiful. New York is like a rock in my shoe. It keeps me moving ahead. What do you do to keep yourself out of your comfort zone? To keep yourself moving forward?
Sarah: I got fired twice in my twenties. Back-to-back. It was a shitstorm of the highest degree. Nearly got deported. For so many reasons, I deserved for that to happen to me.
But in the last couple of years, I realized that I had gotten comfortable. In my past, I was so good at screwing up and having it done to me. Someone telling me, “It’s over,” is very uncomfortable. Here, I was like, “I can take this into my own hands. It’s not going to be easy, but I’m willing to take the risk and see what happens.”
Ann: Writing a book, launching a platform, that’s completely uncomfortable. To be your own brand is a totally different way of thinking.
If I could solve any problem for you, wave my magic wand, what problem could I solve?
Sarah: I would like you to slow the world down. Get me an extra day every week. All those years in my twenties and thirties were, with young children, full-on. You are doing so many things at once. You suddenly wake up and go, “Shit! I’m 45 next week and my oldest kid’s only got six more summer holidays before he’s gone.” I can’t even deal with that.
Ann: What would you do with another extra day a week?
Sarah: I would play a lot more: travel, cheesy dance parties with my kids.
But in the absence of that day, I love my work, and don’t for a second have any regret or sadness that I don’t have that day. And when you are so passionate about what you’re doing, and working really hard and grinding it out, when you have those moments of play they are so joyful. When I look back I realize now that you need both sides. The big life is all of it.
Ann: It’s all of it, but not in a neat, orderly, balanced way. It has to be a mess. Because if you try to make everything fit into neat little bento boxes you are going to crush your mojo.