The Bregman Leadership Podcast
Episode 99

Sarah Robb O'Hagan

Extreme You

What are the qualities that make people extremely successful? Sarah Robb O’Hagan would know; she has been named one of Forbes’ “Most Powerful Women In Sports” and was formerly global president of Gatorade. Her new book, Extreme YOU: Step Up. Stand Out. Kick Ass. Repeat, wants to make you an Extremer, too. Discover the five essential qualities of an Extremer, how to tell if you’ve found the career you’re best suited for, and a practice to overcome your fear of failure.


Book: Extreme YOU: Step Up. Stand Out. Kick Ass. Repeat.
Bio: Executive, activist and entrepreneur, Sarah Robb O’Hagan has been described by the media as everything from “Superwoman undercover” to the “Pied Piper of Potential.” She is a high-energy combination of disruptive business leader, fitness fanatic, and cheerleading mom, and has been named one of Forbes‘ “Most Powerful Women in Sports” and one of Fast Company’s “Most Creative People in Business.”


Peter: Welcome to the Bregman Leadership Podcast. I’m Peter Bregman, your host and CEO of Bregman Partners. This podcast is part of my mission to help you get massive traction on the things that matter most. Sarah Robb O’Hagan is with us today. She’s an executive, an activist, an entrepreneur, and the founder of Extreme You. That is the name of her new book, Extreme You: Step Up, Stand Out, Kick Ass, Repeat. Sarah led the reinvention and turnaround of Gatorade, as its global president. She was also most recently president of Equinox Fitness, so she’s had a tremendous amount of experience as a leader in several organizations and leading turnarounds, and Extreme You is both a personal and professional book. It’s about how to show up being the best that you can be. Sarah, welcome to the Bregman Leadership Podcast.

Sarah: Thank you for having me. It’s awesome to be here.

Peter: Sarah, what is an extremer? What are some good examples of extremers?

Sarah: I basically took about three years to research and write the book. In that time, I interviewed some people that I would call extremers that are some of the most successful people in the world from all walks of life. From business, like Angela Ahrendts from Apple, to Condoleezza Rice, our former Secretary of State, to Bode Miller, the downhill skier. I’m talking all sorts of different expertises, if you will. What I’ve learned from all of them, and why I call them extremers, is because they are people that are relentlessly living to the best of their own potential. What that means is that they’ve really deeply understood what their unique sort of skills and passions are, and how to keep developing those to make yourself be the best that you can be, instead of getting distracted by comparing yourself to others, and all those sorts of things.

Peter: You start the book by talking about the importance of not being perfect. On the other hand, you look at these Condoleezza Rice and Bode Millers, who have certainly reached a level of perfection and extreme success that most of us will never be able to achieve. How do you balance those two things?

Sarah: Yeah, it’s a great question. What’s interesting is I loved when I did the interview with Condoleezza Rice. I said to her, “How does one become the Secretary of State?” She goes, “Well, I was a failed piano major.”

Right there is the answer, right, to, “What is perfection?” I think, often from the outside, we can perceive these people to be very perfect, and to have these flawless career journeys, but in every instance, the people that I interviewed, and certainly on a more broader scale, a trend that we’re seeing is that to get to the best of your own capability, there’s undoubtedly been things that have gone wrong, on the way, mistakes you’ve made, failures you’ve overcome, and ultimately, resilience that you’ve built, as a result of it.

I think every one of the people I spoke to would have said they don’t really consider themselves perfect. It’s the rest of the world that makes it look that way.

Peter: It’s interesting, because to be that successful at something has got to come at a cost, I would imagine. Right?

Sarah: Yeah, yeah.

Peter: I’m curious … Before we even go into the conversation about what are the qualities of these extremers, and how do we integrate them into our possibly more mundane lives, what’s the cost of that kind of success that you saw in the people that you interviewed?

Sarah: I would say the biggest cost, honestly, was having to accept the consequences, both good and bad, of decisions made. What I mean by that is that I think, in general, the people that don’t reach their same level of their own potential and breakthrough, in the same way, are generally people that didn’t want to take the same risks and had a more comfortable path. Whereas those who really break through and reach their extreme levels of potential have generally had heartache, along the way. They have made sacrifices. They’ve had to give up everyday things to really focus on their own passion, or mission, or whatever it may be. But most importantly, I think they have suffered failures, and difficulties, along the way, and pushed through. That’s a very lonely journey, when you’re doing that. It’s not something you can necessarily share, when it’s your own dream, and your own purpose, that you’re chasing.

Peter: Bode Miller, certainly famously, has also gotten himself into some trouble with, I believe, drugs and alcohol … Maybe I’m just picking out specific people, but you look at a Britney Spears. This kind of success, and this sort of extreme focus can be a little overwhelming. Now, even as I say that, we all know plenty of people who are not extremers who have problems with drug and alcohol. It’s certainly not a stressor that is reserved to the most highly successful, but it does seem like the weight of that kind of a focus can be overwhelming.

Sarah: Yes and no … One thing I think that is very important to state is that being an extremer doesn’t necessarily mean that you are on a world stage, like driving progress in the media spotlight. Some of my favorite extremers are actually people that are doing things very quietly behind the scenes, in their own way, but actually really pushing their own potential, and pushing themselves to achieve their own personal greatness, if you will. I want to make sure I was clear. Being an extremer isn’t “being successful.” It’s more living at the best potential of what you, personally, can be. To the point you just made, I do think in life, people can get into trouble. They can come across problems like drugs and alcohol. But I would say the people that I have studied and observed who have gone on to reach their potential have overcome those, and figured out how to get back on track with their own life, and their own career. Issues like that, are those problems to overcome, or are they part of your journey that helped develop you that you learned from?

Peter: You talk about five essential qualities of Extreme You. Right? These are the things that all of us can, I think, nurture in ourselves in a sense, in order to become the best version of ourselves. Could you give just a sentence or two about each one, so that people have a sense?

Sarah: Yeah. It starts with what I call openness to experience. That is a willingness to try new things, and not be afraid to try new things. I think that’s something that I really saw that all of these people had in common, is when there’s a fork in the road, and it’s an opportunity that takes you to a scary place, they would say yes, whereas many people would say no. Also, maybe, being willing to try things that don’t even necessarily seem like they’re on the straight and linear path to a “successful place,” but you’re willing to just try it to get out of your comfort zone. That was definitely one.

Internal drive is another. The sort of get up and go that these people have. They’re not really needing other people to necessarily push them, but they have it themselves, and they cultivate it in themselves. I don’t think drive is something that you’re necessarily just born with. I think you can really cultivate it, and one of the things I studied and learned from these people is how to do that. By making sure you’re sort of setting goals that are achievable, but pushing yourself to get that sense of fulfillment and excitement that comes with “the win.”

Then, I would say there was a big one around grit and resilience, in terms of the willingness, or at least the capability, to push through the tough times. That probably trumps talent, I would say, any day, and all of them would have agreed with that. When things go wrong, you’re able to keep pushing yourself through, to get to your desired end state, and you’re able to pivot, and not get knocked over by failures, if you will.

A personal favorite of mine was the quality, I call, getting over yourself, of humility. This stubbornly humble ability to just go through life, no matter how successful you are, still recognizing that you can be better. That there are other people in the room that are just as smart, if not smarter, than you, and the curiosity, quite honestly, to keep learning, and keep growing, coming from that perspective.

Then, the last one is around risk taking, and I think all of these people definitely had a willingness to take bigger risks. To accept the consequences. To not look for the safety net that, “What if it goes wrong? I need to have an out clause,” but instead, “I’m going to take this risk. I’m going to go for it. I recognize that it might fail, and I’m going to take that failure, and drive on, as opposed to being scared of trying, at all.”

Peter: You also talk, in this chapter, of check yourself out. Understanding yourself, and what your strengths are, and what your capabilities are. When you talk about Condoleezza Rice being a failed pianist, and yet, becoming a very successful Secretary of State, that it’s understanding what you’re particularly suited for that might be different than what your expectations are, or what other people’s expectations are, of you.

Sarah: Yeah. Definitely. No, I think that’s one of the things that I’ve really discovered, in this journey. I think today, particularly young kids coming out college, there’s such an expectation A, that you’re going to have a perfect resume. That everything’s gone right, and there’s no screw ups, and B, that you’re going to follow this very linear path to a sort of end goal place. What I really learned, from this process, is that is not how the most successful people get to where they’re going. In actual fact, they have many forks in the road, where they might go to the side, for a little while, before they progress forward, because this process of checking themselves out, of trying multiple different things, is ultimately adding out to something much more complete.

I give my own personal example. I started my career in the airline industry. I remember spending a year or so in the revenue management, which was so boring I wanted to jump out of a building. Yet, who would have thought that that exact experience would be so useful 25 years later, when I’m running an indoor cycling business. Bums on the seats, but just on a different kind of seat. I think you don’t realize that some of the experiences that may feel boring, they may feel like they’re not in service of the original goal where you want to go to actually are adding up to something. You’ve got to be willing to get in there and try them.

Peter: Yeah. It’s interesting, ’cause a lot of people will say, “Take a career test, or a personality assessment,” or, “Have some external advisor tell you what to do.” But you’re saying, actually, to stay curious. I think that’s really hard for people. I think it’s hard for people, one, because we have blind spots. We don’t know what we don’t see. I’m not a huge fan of personality tests. On the other had, I think one gift of them is that they may show you something that you don’t necessarily see about yourself. But also, people struggle with it because I think staying curious and examining your life is very hard for people. Why? Actually, probably more important than why, what have you seen that helps people get to that place of refining their path, based on their own curiosity of themselves?

Sarah: That’s a good question. I think it’s not necessarily a kind of, “I’m going to make a mark on my calendar, to sit down and reflect, and make decisions,” but I think it was generally as they were making significant life decisions they were purposefully looking back on decisions that came before it, to understand how to move forward. If you have experienced a lot of things, and I talk, in my book, about experiencing the extremes of incredible success, and incredible failure, you are, by definition, honing your intuition to where you thrive, and I think, again, I’ve shared my personal experience … I got fired twice, in my 20s, before I went on to work for Nike, which was an environment I absolutely thrived in.

Had I not had both experiences, of being in environments that were very tough for me, being in good environments, I wouldn’t have had such a strong intuition when assessing job opportunities later, in my career. I think sometimes, that’s what people miss. In this desire to progress as fast as they can, they’re not recognizing that actually, sometimes, the not so good experiences are helping to hone your intuition, and your decision making, for the future.

Peter: As I listen to you, it occurs to me that you need a tremendous amount of confidence to do what you’re talking about. You need the confidence to be fired, a couple of times, and then get up and keep going. What you’re calling resilience and grit. You need the confidence to say, “I’m actually going to think about myself, and how I can bring myself closer.” Almost an entitlement, to say that I deserve to be in a position that really leverages the best of my skills. The idea of the drive, and even the confidence to get over yourself, there feels there’s this underlying confidence that’s really critical. I’m curious about, for people who might struggle with that kind of self confidence, what advice can you give for people to develop, or grow, that underlying foundational skill to being an extremer?

Sarah: Yeah, it’s a great question. I quite passionately believe that it actually starts with great parenting. I feel really lucky that I was raised by parents that did not helicopter parent me. They did not give me trophies for showing up for school. I am 45 years old. I have still never won a trophy in my life. I’m still trying. My point is, how that plays into confidence is that when you are left to your own devices, to basically deal with your own failures, and your successes, on your own terms, you get the feeling of self belief that comes with surviving a difficult situation. Everyone often says that to me now. “Gosh, you’re staying so confident.” I’m like, “Well, yeah, when you’ve been through really difficult situations like being fired, and survived it without someone else backing you up, and getting you out of the ditch, of course, you’re going to be more confident.”

How do you do it? It only starts with baby steps. I’m not suggesting that everyone who lacks confidence should throw themselves into a really difficult career situation, and see what happens, but baby steps can be, in any place in your life, you can choose something that puts you out of your comfort zone that you can push through. I’ll give you an example. A year ago, after I had chosen to quit my job, which was one of the most scary things I’d ever done in my life, I was like, “Well, what am I going to do to develop a new side of myself?” I went and took music lessons, piano lessons, with one of my kids. Unbelievably terrifying, to be playing piano in front of an instructor. My fingers were shaking, et cetera. But getting through it, by the end, you just get this little burst of, “Wow, I did that.” That, then, applies to how you feel about other aspects of your life. Confidence building is like going to the gym and building muscles. It has to be done every single day.

It’s not something that you just sort of develop, and it’s there forever. I truly believe you have to keep working on it, because things come along, in your life, that make you feel confident or unconfident. You have to learn to develop the tools to overcome the tough times.

Peter: I’m going to ask you a strange question, here, as I’m listening to you. It’s coming to mind. It goes a little bit to the core of all of this, and it also goes to the core of our society, and the way in which we tend to focus ourselves, or we tend to be focused, with all the media, and the self-help, et cetera. Is it actually really important to be the best that you can be? It goes back to the cost of it. But there’s so much emphasis on being the best that you can be, and it occurs to me that maybe that’s not such an important thing. It may be, but maybe, it’s worthwhile to be good enough, and balanced, and not extremely amazing at any particular thing, but having a strong foundation of a happy life, in whatever way that means, in relaxing, and taking vacations, and working. But not necessarily being the best that you can be. I’m curious to get your perspective on that.

Sarah: Yeah. I think that’s a really valid, cautional concern. I definitely think that the world, the cultural landscape we live in today, puts such an emphasis on success. That’s actually why I shy away from the word success, ’cause I think that it’s just a dumb word. In whose mind? I have people telling me all the time, “You’re so ‘successful.'” I’m like, “Well, that’s what you might think, but to me, I’m learning and growing. I’m still working on things.” I think, ultimately, being incredibly fulfilled is what we should all pursue. That’s the most important thing of all. That’s, to me, what I equate to living to your own potential. That’s up to you to define what that looks like, right? But I definitely agree with you, that when we get into a world where everyone’s feeling like they just have to be a leader, run things, be better off than the next person, if that’s not what makes you happy, then why would you do it?

Peter: Right. Right. Maybe being the best you can be, it seems so counter intuitive, especially culturally, but maybe being the best that you can be, for some people, and maybe for many people, isn’t actually the right frame. It’s interesting. It’s just something to think about, and for listeners to think about. There’s a gut response that we should all be the best. We should all reach our potential. I guess I’m at least asking the question, or suggesting, that at least in this check yourself out phase … One of the qualities of Extreme You is check yourself out, to check yourself out with that question. To say, “What is important to me? Maybe, in some ways, reaching my potential isn’t.” Which seems so certainly countercultural, but it’s an important question to ask.

Sarah: Oh, absolutely. Absolutely.

Peter: In the book, you say that the worst thing is not failure. It’s fear. I think that feels really important, and I just wanted you to expand on that a little bit.

Sarah: Yeah. I’m quite passionate about this topic, ’cause I do spend a fair bit of time speaking to and mentoring young people coming into the workforce. It’s alarming to me how much of an issue fear has become for the current generation. I hold my generation accountable for creating it, because I think that if you go and speak to a room full of college students, and say, “Hands up, who has a fear of failure?” Every single hand will go up in the room. It’s this mortifying fear, and I think it is because they have been raised with this expectation of perfection. This expectation of perfect grades, perfect extracurriculars, perfect everything. There’s this fear that, “If I screw up, I’m going to fall down the rung on the ladder, and I won’t get a job, and I won’t get this, and I won’t get that.” It’s just so important for me to try and get the word out to younger people, starting their careers. That’s why I interviewed 25 incredibly high potential people, in the world, to prove out my theory, which is that you have to fail to … Really know who you are, at your best.

You have to fail. Therefore, getting sort of stuck in the middle of the road with fear, and just not trying anything at all, means that you’re, by definition, not developing yourself. Whereas if you take a risk, and you fail, even when you fail, as painful as it is in that moment, you’re growing so much more, and learning so much more, than if you didn’t … Young leaders, you don’t really get told, in your 20s, what it’s going to feel like, in your 40s, when you have hundreds, if not thousands of people, who are reporting to you, and you are trying to make giant decisions, in tough economic times.

It is hard. It takes incredible resilience to do that. If you haven’t been what I call battle tested, in terms of knowing how you react to failure, and how to process it and move on, it’s going to be tough for you, when you get into those more high pressure situations.

Peter: That makes total sense. It’s completely rational. It’s true, and yet people still feel that fear, and that fear still blocks. I guess my question is what you’ve seen in the extremers, or what you’ve seen that helps people develop their resilience to fear. Or, have the people you interviewed just naturally, either because of parenting, or because that’s their personality and constitution, have a higher threshold for failure? Or, is there something aside from what we talked about earlier, which is take little risks and fail in little ways, and then see that you’ve survived it, and then go to bigger ones. Is there something else that can help people who are listening develop their strength and grit, in the face of their fear?

Sarah: Yeah. I do think, without question, it comes with experience. For sure, at least all the research I’ve done, is you can’t go to college and take a paper on how to overcome fear, or how to deal with failure. You actually just have to do it. I do think it starts with taking small risks, and seeing how they go, and dealing with them. But one technique that I, personally, have used a lot that I talk about, in my book, is playing this game that I call what’s the worst that can happen? When you’re making giant decisions, and you’re really scared of them, and it’s going to hold you back from making them, really think through what’s the worst that can possibly happen?

More often than not, you’re going to get to realizing that you can recover from it. I can think of countless times when, in my case, it’s like what’s the worst that could happen? I could lose my job. I could be deported. I could go way down the list of how bad this could be. But actually, you get to the end point, and you’re like, “Well, if all that happens, I still have my health. I have my family. I have all these great things. By the way, I have a bunch of capabilities that are immediately hire-able, and I’m going to be able to get on with it, and find another job” … If you play that out, you almost can get control of the fears that are often stories you’re telling yourself, as opposed to realities.

Peter: I love it. Final question. How has your life been impacted by this book? How has it changed how you approach your life, based on all these interviews, and everything that you discovered in the three years of writing the book?

Sarah: Yeah. Hugely. More than I expected, actually. I feel like what it has helped me to do is understand a methodology that I can sort of guide myself back to, when I’m making decisions, and when I’m trying to understand how I want to go about being a leader. If I think a lot of things that I had experienced in my life, or techniques I was using, I’d learned from other people, but I’d never taken the time to really do the research to understand why something works. Now that I have, I think I just feel so much more, what’s the word? I feel like I want to hold myself more accountable to a higher standard of helping to develop others, with these amazing insights that I have learned, because I feel like it was an amazing gift, to get to interview these incredible people, and hear their stories. It’s definitely great wisdom that I want to share.

Peter: Well, thank you for sharing it. Sarah Robb O’Hagan. Her book is Extreme You: Step Up, Stand Out, Kick Ass, Repeat. It’s been a pleasure having you on the Bregman Leadership Podcast. Thanks so much for being on, Sarah.

Sarah: My pleasure.

Peter: I hope you enjoyed this episode of the Bregman Leadership Podcast. If you did, it would really help us if you subscribe on iTunes, and leave a review. A common problem that I see in companies is a lot of business. A lot of hard work that fails to move the organization as a whole forward. That’s the problem that we solve with our Big Arrow process. For more information about that, or to access all of my articles, videos, and podcasts, Visit Thank you Clare Marshall for producing this episode, and thank you for listening.


  1. Armando Cordova says:

    Very well presented. A good reminder to all that the best way to achieve our potential is to keep learning and growing. Being the best you can be, after all, is a journey, not a destination.

  2. Viet Tran says:

    Thanks for the transcript, Mr. Peter Bregman.

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