Fewer Trophies, More Mistakes: Flywheel Sports CEO Sarah Robb O’Hagan On The Entrepreneurial Spirit

From Flywheel Sports Instagram

Photo from Flywheel Sports Instagram

In 2016, Sarah Robb O’Hagan resigned from a top job at Equinox to answer a question: Why were young employees becoming so afraid of failure? Her answer, Extreme You, is both a book and a movement about maximizing human potential and changing our culture. It calls for fewer ‘participation trophies’ and more growth through mistakes.

Today, Sarah brings Extreme You to Chicago Ideas Week where she’ll give a talk at the program Innovating from Within: When the Entrepreneurial Spirit Never Stops. I spoke with Sarah to learn how she applies Extreme You to launching, scaling and turning around companies. From Virgin Atlantic, Nike and Global President of Gatorade to her current role as CEO of Flywheel Sports, Sarah has grown through taking risks. In this Q&A, we go deep into her entrepreneurial approach:

Jayna: Sarah, your career has changed significantly since you left Equinox last year. Today, how would you answer the question, what do you do and how do you do it?

Sarah: I’m currently CEO of Flywheel Sports, an indoor cycling company that’s about to become an online cycling company. We’re nearing the launch of an at-home bike where you’ll be able to stream our epic classes both live and on-demand.

As for how I do it, I’m in the business of helping people unleash their own potential. That’s what fitness is all about. I mean, why do we work out? It’s generally because we want to strengthen our bodies and minds and get more out of our lives.

Jayna: Tell us about the difference between leading a brand and launching one. What has been unexpected or challenging about starting Extreme You?

Sarah: I feel lucky that I’ve worked for iconic brands like Nike, Gatorade and Virgin. When I set out on my own and started to work on Extreme You, it was amazingly difficult and different because there was no roadmap.

At established brands, like Flywheel, you spend the first few months indulging in the heritage story. It’s a source of inspiration. But when you’re starting from scratch, the boundaries are so wide that you need something to pull you in.

That was hard for me. With Extreme You, I researched psychology and interviewed a lot of people. I used their stories to identify common themes and refine down to a core idea. It was quite a fun growth process, but it took a long time to land on the right idea.

Jayna: What was the big insight? When did you realize that you were onto something?

Sarah: I was interviewing extremely successful people from very different walks of life. When you talk to Condoleezza Rice, Bode Miller and Mister Cartoon, the famous tattoo artist, the three couldn’t be more different. Yet as they talked about their life journeys, their careers and the methods they use to get the most out of themselves, I noticed commonalities in language and thought process. That’s when I realized I was onto something.

There is a reason why certain people outperform others. It goes beyond natural talent or being born in the right home. It is all to do with how you understand your unique traits and exploit them to the max potential.

Jayna: What motivated you to launch Extreme You? How does it help people maximize their potential?

Sarah: It came down to a few things. First of all, I’m a parent of three children, and I was horrified to see my kids come home from youth soccer with ‘participation trophies.’ I connected the dots between that and what I saw amongst the new generation coming into the workforce.

I speak at a lot of colleges, and students always talk about their fear of failure and the pressure to be perfect and not make any mistakes. I suspected that these fears came from being given trophies throughout life just for showing up. These students hadn’t been pushed to fail, make mistakes and grow from them.

That cultural shift concerned me and led me on this exploratory journey. I wanted to see if, in fact, that the people who’ve achieved success are those that have made lots of mistakes, embraced them and grown with them.
Jayna: How is your approach to dealing with fear of failure different from other approaches out there?

Sarah: It comes down to worrying less about the outcome and more about this question: In everything you do, are you developing yourself?

Culturally, we tell people to make five-year career plans. If you have such a plan, you don’t want to make mistakes and fail because you want to reach the five-year goal as quickly as possible.

You see failure differently if every decision starts with the question, “Is this pushing me and developing me in a new way?”

You’ll take risks and have no idea if you’re going to succeed. If you do succeed, awesome – that’s going to move you faster to your next opportunity. And if you fail, that’s awesome too because it will teach you things that progress you forward.

The outcomes arrive if you develop yourself and get to know yourself better. But if you just focus on the end goal, you’ll be less likely to take risks.

Jayna: The Extreme You manifesto talks about this idea that you need to “get out of line” to achieve your potential. Can you share what that means and an example from your career?

Sarah: There are moments when you’re amongst a peer group and you can either choose to jump up and grab an opportunity, or you can choose to wait in line. Getting out of line is taking that opportunity.

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