Extreme Career Success: An Interview with Sarah Robb O’Hagan, CEO of Flywheel Sports

EXTREME YOU: Step Up. Stand Out. Kick Ass. Repeat. How could you hear that book title and not want to dive right in?

The title won me over right away, as did its author Sarah Robb O’Hagan when I had the pleasure of meeting her for coffee in New York last year.

Sarah is CEO of Flywheel Sports and former president of Gatorade and Equinox. The book is honest and refreshing: Sarah, who is wildly successful today, shares what she calls her early career “epic fails,” like when she was fired twice in her twenties. Someone with less drive might take that as their cue to exit stage left, but Sarah came back stronger than ever.

In addition to her own personal tales, the book includes stories from a group of “Extremers” ranging from entrepreneurs and corporate leaders to a former secretary of state, an Olympic champion downhill skier and even a world-renowned tattoo artist.

The bold goal of the book? To help you “rock your career and live the boldest version of yourself.” I love it.

I caught up with Sarah to find out more about how her failures became (extreme!) successes and what advice she would share with today’s go-getters, including the many college seniors who are just starting their careers after graduation this spring.

You were fired twice and have had career ups and downs. What lessons can young professionals take from perceived career setbacks?

It’s very clear to me that my wrong moves are what led me to my best right moves. We’ve all heard people say that it’s safest to make the decision at work that won’t get you fired. Well, I massively disagree with that thinking because I’ve seen with my own experiences that the safest choices are actually the ones that can lead to the whole company going out of business — and then people really do lose their jobs.

I got fired not once but twice (from Virgin and Atari). Having been through that experience — the humiliation, the self-reflection and ultimately the learning and strength that came from it, I became pretty fearless in my career because I knew I could survive losing my job.

I was never really one to conform to making choices because they were “safe,” but what the firings taught me was that even though my ideas were good and actually might have been good for the company, my approach to execution and how I brought them to life within the team needed a lot of work.

By the time I got to Gatorade, which was a company whose growth had stalled, I’d seen this movie before! I knew that playing it safe and chasing the competition was a recipe for certain disaster. So I had to be bold — to suggest that we walk away from the consumption that was dragging the brand down, and to totally rebuild it with authentic products for athletes.

And by this time I had the self-awareness to know how to ask for support and help, how to get my ideas across, and the courage to swing for the fences because I knew I was a survivor. I’m utterly convinced that I would not have succeeded leading the turnaround of Gatorade had I not experienced those tough moments early on.

I owe my biggest successes to letting myself fail and building from these experiences a confidence about throwing myself outside my comfort zone so I could tap my full potential. That’s the Extremer approach that I hope everyone can learn and benefit from in their own careers.

I love your mantra that you’ll achieve more if you’re willing to step up — and out — of line. How can millennials apply that thinking to their careers?

​Well, it definitely starts with having the courage to take risks — and seize opportunities that others around you might not. There will be many moments in your career when a door opens, and it requires you to go in a different direction than what you had been planning.

It might be a relocation, it might be taking on an aspect of the business you thought you had zero interest in; it may even be something that looks like it’s not a great door to be opening — take for example a project that you can see a team working on that is clearly failing, maybe if you jumped in you could be part of its turnaround!

The point is — those are the clutch moments that you have to seize with both hands and jump in boots and all. Often they will feel inconvenient or outside of your comfort zone — or they may require to work after hours to get the job done. But trust me, THOSE are the moments when the Extremers emerge — through the learnings you gain personally and the reputation you gain for yourself for being willing to step up in service of your team.

You’ve mentioned that many junior employees seem to think that if they just do what they’re told and work hard to please the boss, they’ll get safely promoted, but that’s not the business world today. What do you think younger professionals need to do to stand out?

We send so many mixed messages to young employees. With social media showing us nothing but perfectly coiffed lives and careers, and cultural messages to young people saying that they need the “perfect” resume to stand out from the crowd, we give the impression that the way to achieve great success is simply to conform, not rock the boat and please the boss.

But trust me — I can say this as a boss — the boss does not have all the answers. HELL NO! The reality is that it’s the employees who have the courage to push boundaries and own the consequences of their actions — both good and bad — that are the ones who eventually drive the business forward and often in the process leapfrog their peers.

So the entire intent of my book is to blow up these false assumptions — I’ve curated some of the most inspiring stories of extraordinary success on the global stage to show that it’s not a straight perfect path to get to maximizing your own potential.

I agree that it doesn’t really matter if you don’t yet know what you’re good at or what goals to pursue at a young age. What are some ways that this evolves throughout the early part of your career?

I have spoken to many amazing ambitious people at the start of their careers who feel such pressure to have this perfect path mapped out. Not to mention we tell everyone you have to find your passion if you are going to be happy! Talk about pressure! To be honest, I didn’t truly discover my passion until well into my 30s, and I know my story is not unusual.

It takes time and lots of willingness to try new things to discover what really blows your hair back and find the environment in which you can most truly shine. So I try and remind young people to be patient and not worry. Your interests will change with time and experience and so will your skills and your knowledge of yourself. Just focus on getting involved with as many varied experiences as you can so that you can tune your own radar to know what makes your heart beat!

You manage a lot of millennials. How can managers get the best from their millennial employees?

Be a great boss by bringing out the Extreme in others. One of the things I LOVE about managing millennials is that they push me, they teach me and they help evolve my own knowledge because they bring so many new ideas to the table.

One of the reasons I wrote my book was because I felt there was so much opportunity to be had from intergenerational learning. I think there are a lot of oldies like me that can deeply benefit from the boundless thinking of the millennial generation, and likewise I think that the millennials can learn a lot from some of the time-tested experience of their older peers. The best teams I have been a part of that have driven tremendous business successes are those where we were able to come together to unleash the best in each other.

What advice would you give to this spring’s new graduates?

Do not worry if you can’t find the perfect first job. What matters is that you get in the game, anywhere, anyhow. Work in an office doing the grunt work. Work in a bar. Be like me and do a research study of the sandpaper market where you have to go and learn about why different sandpaper works for different tasks (really!).

One of my favorite Extremers in the book was, according to his friends and family, “bumming around Europe” and doing the excruciatingly hard work required in a restaurant kitchen to pay the bills. Little did they know that he was beginning a journey that would lead him to becoming the White House chef! You simply don’t know where your path is going to lead you, but if you’re not in the game you’re not learning, and if you’re not learning, you’re missing out on discovering Extreme YOU!

Thank you, Sarah!

Readers, which advice most resonates with you? If you’ve discovered your passion, when did that happen? Are you an Extremer like Sarah? I’d love to hear in the comments below.


Lindsey Pollak is the leading voice on millennials in the workplace, trusted by global companies, universities, the world’s top media outlets — and, most importantly, by millennials themselves. A New York Times bestselling author, Lindsey began her career as a dorm RA in college and has been mentoring millennials — and explaining them to other generations — ever since. Her keynote speeches have audiences so engaged that, in the words of one attendee, “I didn’t check my phone once!” Contact Lindsey to discuss a speaking engagement for your organization.

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Lindsey is a globally recognized career and workplace expert and the leading voice on generational diversity. She has spoken for more than 300 audiences including Google, Goldman Sachs, Estee Lauder, Stanford and Wharton. Lindsey is the author of four career and workplace advice books, and her insights have appeared in media outlets including The TODAY Show, CNBC, NPR, the Harvard Business Review and the Wall Street Journal.


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