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Sarah Robb O'Hagan: 'I Learned to Win By Failing'

Sarah Robb O'Hagan, author of "Extreme You," shares what she learned on her way to the top and what she thinks it takes to be successful and win.

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This Is What It Takes to Win

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In her new book "Extreme You: Step Up. Stand Out. Kick Ass. Repeat," Fly Wheel CEO Sarah Robb O'Hagan describes her abilities as a child and a teen as average: She never made the A-team or even got straight As. But this average kid from New Zealand turned out to be anything but ordinary.

Robb O'Hagan made her mark on the business world by breathing new life into brands like Virgin, Nike, Gatorade, and Equinox.As a result, she was named one of Forbes' "Most Powerful Women in Sports" and one of Fast Company's "Most Creative Women in Business." Despite her impressive CV as president and CEO of some of the biggest sports brands in the world, she felt like her success story left out a very important piece: her failures.

In her book, Robb-Hagan interviewed 23 successful women and men from varying backgrounds, including Secretary of State Condoleezza Rice and Olympic gold medalist and skier Bode Miller, to bring to light what makes average people become so extraordinary. She sat down with NBC News BETTER to talk about failing, feeling like a fraud and, ultimately, winning at work.

This book is about success, but it’s also about allowing yourself to be vulnerable and make mistakes. What does “Extreme You” mean?

Sarah Robb O’Hagan: "Extreme You" is ultimately what I call living at the edge of your own potential. So that means really understanding who you are, what you love, where you suck and where you're good so that you can figure out where you play to your best. And then really sort of push yourself to get more out of you every single day. It’s about being vulnerable, and it is about failing on the way to succeeding.

You say you were an average kid. What were you like?

Sarah Robb O’Hagan: You know, never got the lead part in the play, never got A grades, frankly. And I just was one of these people with quite sort of average skills. But I just kept pushing, because I kept thinking if I try and push and learn and discover, surely, eventually, I will have some success of my own. And that's really what the whole book is about, is that you can get there as long as you have the sort of the grit and the resilience to discover the best of who you are.

Image::"Extreme You: Step Up. Stand Out. Kick Ass. Repeat" by Fly Wheel CEO Sarah Robb O'Hagan.|||[object Object]
"Extreme You: Step Up. Stand Out. Kick Ass. Repeat" by Fly Wheel CEO Sarah Robb O'Hagan.

You were successful in your 20s, but you also had some failures.

Sarah Robb O’Hagan: Yeah, so in my 20s, I got fired once and laid off once, back to back. So I fondly call it my "canyon of career despair." It's the time when most of us in our careers are really getting going, you know? And it just all went pear-shaped for me. It went all backwards.

But eventually, I started to realize that if I was really honest about it, it was my problem. And I was way over my skis in a job where I just didn't have the sort of foundational capability to do what I needed to do. And I was kind of blindly going along doing my own thing because I'd had successes in the past. And it was a huge, huge learning.

You mentioned feeling like a fraud at that time.

Sarah Robb O’Hagan: I can remember joining Nike when I was in my late 20s, having just been laid off twice feeling like a total fraud, because I was surrounded by these incredibly intense, competitive, highly talented people. And I'm sitting there every day going, "Oh my God, oh my God, they're going to find out I got fired. They're going to know I'm useless," you know?

When we think of successful people, we tend to imagine that they came up with one goal and then just crushed it for the rest of their lives, but that’s not true, is it?

Sarah Robb O’Hagan: 100%! I've researched and interviewed 23 of the most successful, accomplished people on the planet. I'm talking everyone from Condoleezza Rice to Bode Miller, the downhill skier, to Mr. Cartoon, who's a famous tattoo artist. These are extraordinary successful people.

And what I found in every single instance is none of them knew when they started that that's what they were going to become. And I actually learned that our whole kind of perception of success, especially when you're young, is a little bit backwards.

Extremers, by definition, are not well rounded. They're very passionate and very skilled in certain areas, and not in others. And that's awesome.

Extremers, by definition, are not well rounded. They're very passionate and very skilled in certain areas, and not in others. And that's awesome.

Because you get so focused on, "I want to get here," but what I found from all of these people is they just focused on developing themselves and making themselves become better in the thing that they love doing.

What’s your advice on how to stay relevant in the workplace as you age?

Sarah Robb O’Hagan: I think one of the most profound experiences of my career was working in a company like Virgin Megastores, one that ultimately went bankrupt when the whole music industry got disrupted. Compare that to working in a company like Nike, which disrupts itself every single day to be innovative and to stay in front of whatever the new technologies and trends may be. I think you can really apply those learnings to yourself as a leader.

I have always felt very passionately that particularly as I get older, it's not okay to say, "Oh, the young kids understand the technology, they can go do it." It's on me to figure out how to stay relevant by understanding it all.

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We talk about winning a lot these days. What does it even mean?

Sarah Robb O’Hagan: Yeah, I actually feel like we've got this weird perception around winning these days. It bothers me that in the last 20 or 30 years, we started this culture of everyone's a winner. Let's give every kid a participation trophy just for showing up.

I do think that we have this idea of winning almost as something that's too easy and accessible for everyone. And the work and the grind that comes with actually becoming a winner in whatever it is that matters to you is actually what triggers the fulfillment and sort of the passion for what you're doing in the first place.

What's the best advice you ever got?

Sarah Robb O’Hagan: My dad always used to say "without risk does not come great reward." And I love that. I mean, I think about that all the time. When I've been at forks in the road of, like, "Oh, this is a scary decision, should I make this move?" That has helped me have the courage to go for it.

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And the worst?

Sarah Robb O’Hagan: I think probably the worst advice has always been from those people who've said that move is too risky, that idea is too risky, don't do it, because ultimately, even if they're right, for me, the act of making those decisions, screwing up ended up being a good thing anyway because I learned from it.

In the end, how did those failures back in your 20s help shape your success today?

Sarah Robb O’Hagan: I think when I made the wrong turns in my career, in the moment, it felt like, "Oh my God, this is disastrous, and this is going to be the end of everything. Armageddon! Sarah's career is over." But actually, I learned years forward that those wrong moves helped me really hone where I was not good so that I could learn to surround myself with people with complementary skills.

And that's a really, really important learning to become the best version of yourself. You can't do it all, and you don't have naturally wide skills everywhere. One of the things that I talk about in the book is "Extremers," by definition, are not well rounded. They're very passionate and very skilled in certain areas, and not in others. And that's awesome.

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