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Want to Succeed? Fail Until You Find Your Passion

Sarah Robb O'Hagan | Feb 1, 2018

Sarah Robb O'Hagan

CEO of Flywheel Sports, Former President of Equinox and Gatorade

I think that the wonderful thing that I learned writing the book Extreme You and interviewing some of the most extraordinarily successful people in the world—I mean everyone from Condoleezza Rice to Bode Miller the downhill skier, Mister Cartoon who is a tattoo artist—I’ve interviewed people from all walks of life who have achieved incredible success in very different areas. 

And what I found with all of them is that even when they achieved success like what most of us would consider the pinnacle. I mean an Olympic gold medal is about as good as it gets, right? They would then say, “Okay, I’m restless to get more out of myself and I want to break myself down and take on the next challenge.”

And that, to me, was pretty spectacular to see. It’s like for them success is not a goal, it’s just an ongoing journey. And every time they achieve something they realize that there’s more of their own potential to unlock. 

So to be Extreme You is to be maximizing every aspect of your own personal potential, and that means really understanding who you are, what are your unique gifts, what are your idiosyncrasies, what are the funny things about you, what blows your hair back and makes you feel amazing? 

And also where are you not as strong? Like where do you suck? Where do things not work for you? And then when you understand that and then really push yourself to maximize everything that is great about you and play your game on your own terms, that’s being Extreme You.  

It’s incredibly fulfilling because I think when you are playing to your greatest strengths, like we’ve all had that experience when you’re in a job or in an environment that just makes you thrive and you come into work every day and you feel super confident and you just can be yourself. And that is what it feels like. 

And the polar opposite is when you find yourself in an organization that just doesn’t sort of fit with who you are and you’re having to edit yourself in and try not to get into trouble or do things the wrong way. 

So it feels pretty amazing to be Extreme You, and it also is generally a place when you are kind of pushing yourself outside your comfort zone. Like you have the confidence to take on bigger challenges and things that you haven’t done because you know that you’re playing to your strengths. 

So the first thing I definitely say is, it’s about what I call “checking yourself out”. And that means like really understanding what you love and what your greatest skills are. 

And it’s funny, like there’s a lot of media around there today saying to young people, you know, “Find your passion and then you’ll be happy.” And I’m like, “You can’t do a Google search and find your passion!” 

You actually have to get out there and try stuff, you know? And get in there and really try it. Do it. Like experience all sorts of different things. Because that’s when you’ll notice where you really shine and frankly where you suck. 

I mean I personally can speak about working in the sports industry, where I just was like a duck to water and loved it, compared to working in the video game industry where I sucked. I mean I just didn’t have anything in common with the products, the people that chose to work there. And the feelings of being in those two different places were equally as important as each other to help me refine what was the most extreme version of where I would thrive. And I think everybody needs to get in and experience the good and the bad to help sort of refine your own filter. 

The reason I actually wrote this book in the first place is I found myself in my late 30s. I had finally, finally achieved some what society would consider successes in my career. I had led the turnaround of a five-billion dollar business as its president which is obviously no small feat. And I started seeing articles that were written that would refer to me, or my bio read out when I’m giving a speech. And it would say, ‘She did this great thing, She did that great thing, She led this company. She’s being called this in the media. She’s amazing.” And I literally would sit there squirming in my chair going, “Oh my god. No one’s telling the truth!!” 

Because the truth is I’ve had some really embarrassing fuck-ups along the way. And I think it’s important for young people to see that those who become successful have had all those moments of uncertainty, all those moments of frankly averageness. I mean I was that classic B-student, never made the top sports team, never made the choir solos. Like never got picked for anything. But still I  managed to go on learning and refining to figure out where I would achieve my personal success. 

And I believe that that path exists for absolutely everyone. But we have a culture of success right now that would say otherwise. Like when you combine the world of social media where all of us are putting these perfectly coiffed pictures into the world, and then you throw in the whole 40 under 40 list, 30 under 30 list—Everyone in the world is apparently crushing it except for you. Like it’s really hard to believe that you can become great, but yet I know from my story that it was possible, and then I went on this mission to interview some really, really successful people to prove my case. 

And I totally proved my case, because what I found in the book—and I effectively codified it into a method of how you get the best out of yourself—was that every successful person in the world did not start knowing that they were going to get there. Pretty much every one of them did not start with these natural god-given talents. Most of them ended up succeeding in a field that was completely different to what they originally expected. So it was a real story of willingness to experience and try things and then eventually figure out where you’re going to thrive.

And I think the last lesson in all of it was that even those experiences early on where you feel like you’ve put X number of years into the wrong career or you’re going in the wrong direction, even when you change directions those early experiences actually contribute to what becomes a great success, and nothing is wasted.


In this video, Sarah Robb O'Hagan discusses some of the experiences and revelations that she had while working on her book, Extreme You. Among the most impactful realizations is how many of the most amazingly successful people who, having achieved the "pinnacle" of a field (such as getting an Olympic gold medal), are never truly satisfied. Instead, they're eager to overcome the next big limit or beat the next goal.

She also talks about the importance of not being afraid to try different things and fail until you find success—and how those early failures can sometimes prove to be the fuel that contributes to eventual success.

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Sarah Robb O'Hagan

Sarah Robb O'Hagan Sarah Robb O’Hagan is described by the media as everything from “Superwoman undercover” to “The Pied Piper of potential.” She is an executive, activist, entrepreneur, and currently the CEO of Flywheel Sports. Formerly, O'Hagan served as the president of luxury health club Equinox, the global president of Gatorade, a GM and marketing director at Nike, and the marketing director of the Virgin Entertainment Group. The founder of the “Extreme Living” movement, she is a rare blend of fierce businesswoman, cheerleading Mom, passionate women’s advocate, and high-energy motivator. In her new book, "Extreme You," Sarah lays out a roadmap for becoming the most “extreme” version of yourself by operating at the edge of your potential and by building highly-collaborative, focused, and successful teams and corporations. Drawing on her decades of experience with some of the world’s most influential brands, she shares practical takeaways including how to make failure your fuel, discover your most competitive playing field, get out of line rather than always following conventional wisdom, and bring out the “extreme” in others.