Enter the Discomfort Zone: Tough Mudder Founder Will Dean on the Key to Confidence

“You just do things that you find scary and after a while, they cease to be scary.”

Sarah Robb O’Hagan is the CEO of Flywheel Sports, has served in executive roles at Nike, Gatorade, and Equinox, and is the author of ExtremeYOU: Step Up. Stand Out. Kick Ass. Repeat. She recently joined Will Dean, the founder and CEO of the obstacle course event series Tough Mudder, for a conversation on the benefits of making yourself uncomfortable, importance of community, and best way to develop confidence.

This conversation has been edited and condensed. To view the full conversation, click the video below. 

Sarah: The Tough Mudder story is phenomenal. How many people have now done it?

Will: Three million by the end of this year. It’s the same as the population of New Zealand.

Sarah: What was the inspiration for Tough Mudder?

Will: I went to business school knowing that I wanted to start a company. While it didn’t need to be curing cancer, it had to be making some positive contribution to the world. I spent a lot of time thinking about ideas, many of which were awful. I started looking at the events space, and had no idea Ironman was even a company back then. I just assumed it was enthusiasts getting together putting on events. To find out it was a real company worth several hundred million dollars blew my mind.

If I can credit myself one big a-ha moment, it was recognizing that doing a marathon or triathlon—for most people, it’s not really a race. It’s much more about personal accomplishment. Understand that a lot of people want to do events [because it’s] social, and it’s helping one another get through it. If you climb Everest, no one asks you what time you did it in. There’s some of that in Tough Mudder, as well.

Sarah: [When you were at] Harvard Business School, [you] actually got reported by the other students for not taking [your] studies seriously enough, right?

Will: It’s true. Nearly all the marks for business school are for what you say in class, and you have a huge advantage if you’re British, because even these learned professors think you sound more intelligent. This created a lot of resentment in the classroom. I was the only English person in my class. Once you make your comment, you don’t get asked to make any more. So in some class, I just said, “I’ve had enough now” and I read my book.

But there was this girl behind me that couldn’t stand the fact that I’d been given honors in the first year for my comments. So she started taking pictures of me on her iPhone and time-stamping them, like “This is Will Dean on this day. He’s made his comment, he’s finished, and now he’s reading.” I had to go explain myself and say, “I’m so sorry.” They said, “Will, you’re detracting from other people’s student experience by not participating more eagerly in class.”

Sarah: Early in your career, what was the biggest thing that you had to do to become the person with the confidence to create this crazy thing that no one had heard of?

Will: There’s so many things. When I first started, I was not at all sure I made the right career choice. Most of the people I was training with thought the same. I was constantly getting these warnings I was going to get kicked off the course. I like proving people wrong, for better or for worse.

“If you climb Everest, no one asks you what time you did it in.”

In England, what tends to happen is [with the] more prestigious career paths like banking, consulting, and law, is there tends to be a lot of people who have gone through Oxford or Cambridge. I’d gone to University of Bristol. Most of you won’t have heard of it, but it’s not a bad university by any stretch of the imagination. I remember frequently, when I was in this program, lots of white boarding school males from Oxford and Cambridge would say, “Oh no, no, no. We’re in the best place. Will’s gone to Bristol.” I took a lot of motivation from that to prove people wrong. Probably have a slight chip on my shoulder to this day.

Sarah: And am I right that your mother kept saying, “Banking would be a great career”?

Will: To this day I think she still believes this. The first time I told her about the company, she said, “If you sold Tough Mudder, do you think you could still get a job at McKinsey?”

Sarah: You’ve got to love parents. Confidence all the way.

What do you remember as your most epic fail?

Will: There are many to choose from. One of the things I remember from early childhood is the nativity play—I was Joseph. This was in the early 1980s, and my parents had rented a camcorder to catch the momentous day. I read my line: “Mary, Mary, we’ve got to go to Bethlehem,” ran, tripped, and my bottom lip smacked down on the ground and my teeth came the whole way through.

Sarah: They’re videoing?

Will: They are. And I thought… I was English, I would try to be quite stoic in these situations. The show must go on. So there I was saying, “Mah, mah, mah” and Mary’s crying and the other children are crying, the teacher had to come up on stage. It wasn’t exactly how it was supposed to go.

Sarah: So your career as an actor?

Will: It was short lived.

Sarah: Fair enough. What about greatest celebrations, greatest success?

Will: One of the things I’ve always been told off for is not taking a moment to celebrate.

Sarah: Really? I see a lot of beer at the end of a Tough Mudder, just saying.

Will: But internally, life’s so busy. It can be hard to take that second and say, “That was worth celebrating,” because you’re always on to the next thing.

Probably the most special memory I have was the day before the first event. It was a beautiful evening, we were going out to look at the course, and I remember thinking, “This thing only existed in my brain 12 months earlier.” I suddenly had this moment of peace and quiet to be able look at it all. I thought, “Whatever happens when we arrive tomorrow, we’ll have a great time.”

That was special, because it went from being this thing that all my professors and most of my friends doubted would ever work. I knew that I had 5,000 people coming, which I was a bit scared about. But it was exciting that it was becoming reality.

Sarah: Which leads me to my next question: what is your biggest “shit-your-pants” moment? I’ve got to imagine that the first 5,000 people showing up—are they going to die?

Will: I have to point out, the most dangerous part of doing Tough Mudder is the drive to a Tough Mudder.

For the first event, the aim was to sell 500 tickets. We’d sold 50-80 tickets prior to a price increase, [which was at] midnight on a Sunday. About 11 p.m., we saw that there were 200 tickets [sold]. We were really excited, thinking, “Wow, we’re going to get to 500.” I had a Blackberry Pearl, and every time we sold a ticket, I got an email.

My co-founder and I went for drinks because we’d sold 200 tickets. I looked at it again and had another 1800 emails. We were ecstatic. We couldn’t believe we’d sold this many. We were refreshing every second, looking at each other in this bar, and were broken, exhausted, because we were working every minute of the day. I remember thinking, “Oh my god. We’re going to have to produce an event for 2,000 people.” No idea how we were going to pull it off.

“The truth is you have no choice but to innovate. Business cycles are so fast now, things that work for a period of time don’t work for very long, and you have to keep changing.”

Sarah: What was the most mortifying feedback someone gave you early in your career?

Will: Being told that I wasn’t mature enough. Being told, “You need to work on your maturity in terms of how you carry yourself, how you behave, and how you look. You look very young.” I remember saying, “That one’s going to be hard for me,” and them saying, “That’s not a particularly mature response, Will.”

Sarah: How did you work on your maturity? What does one do?

Will: Back then, I had about three hairs on my chin, so there wasn’t much I could do in terms of faking that. It was a humbling experience, because you finish university, you think you know everything, and of course you don’t. Suddenly you’re in the real world, no secret sauce. You start thinking you’re a bigshot—it doesn’t get you very far.

Sarah: What are you doing right now to make yourself uncomfortable? [How are] you pushing yourself to grow more?

Will: We talk about innovating, and the truth is you have no choice but to innovate. Business cycles are so fast now, things that work for a period of time don’t work for very long, and you have to keep changing. What it means in practice—doing new things is proven to make you happier. If you want to increase your life expectancy, the best way to do it is to take up a new hobby and try to learn something.

As an organization, we’re doing a number of things. It’s no secret that we’ve been looking at whether there’s something we could be doing in the student space. Something that’s really important is to collect feedback from your peers. The 360 [degree feedback] process is very useful. You always learn something from it. You may not agree with all of it—you may read it and the first thing you want to do is say, “I can’t believe this. I’m going to find out who did this.” But if you take a step back and say, “Actually, yeah, I do do that,” it’s quite humbling. It can be painful, but it’s a worthy process.

Sarah: What do you do that you that irritates the team?

Will: The way I challenge ideas can be quite irritating to people. What I mean to say is, “That’s an interesting idea. Please tell me more.” But apparently it comes across as, “That makes no sense. That’s a dumb idea.”

Audience: Most people who complete Tough Mudder are probably adrenaline junkies. Are you a self-proclaimed adrenaline junkie and what do you do to get that rush?

Will: There’s a hypothesis that most people who do a Tough Mudder are adrenaline junkies. I think that’s true for some people. There are moments in a Tough Mudder that are scary. But there’s a mix. There are some things that are “face your fears,” other parts that are about teamwork and working together, and other parts that are just supposed to be goofy fun. The idea is that there’s a part of Tough Mudder that contests all of us in a different way.

Audience: Tough Mudder tests the limits that your body can [handle] but is there anything that incorporates that mental and emotional limit?

Will: We try to take people on an emotional journey through the event. The regular event is ten to twelve miles, and it’s interesting to see the points [where] different people have had enough. People say, “What’s fun about going through a dumpster full of ice?” The experience of talking about it afterwards. You and someone who did our events in Australia or in Germany have that thing in common. When people have done the event, you’ll see someone in a t-shirt running in the park, another Tough Mudder, and high-five them. You see someone in the gym, you’ll say hi. That sense of community and tribe is important.

“People say, ‘What’s fun about going through a dumpster full of ice?’ The experience of talking about it afterwards.”

One of the things I’m really proud of is the number of people that write to us after the event and tell us how Tough Mudder has had this impact on their lives. They’ll say things like, “I was getting bullied at work,” and they’ll go into the office on Monday morning with their orange headband on and say to their boss, “You don’t get to speak to me like that. I’m a Tough Mudder.”

That comes from doing something that scares you. There’s no secret to developing confidence. You just do things that you find scary and after a while, they cease to be scary. Then you feel better about life, and that confidence bleeds into other parts of your like. “Okay, I did a Tough Mudder, I can take on other things.” That says more about human spirit than it does about us as an event or a company, but I’m very proud of that.

Sarah: You should be. That’s awesome.

We’re going to go to the speed round—one to two word answers. What did you want to be when you were a kid?

Will: A policeman.

Sarah: Which order are you in the family?

Will: The eldest.

Sarah: What’s your favorite swear word?

Will: I try not to swear too much. Bloody hell? Can I use those words?

Sarah: God, you make me feel so bad.

Will: What’s yours?

Sarah: “Fuck”!

What scares you?

Will: Brexit.

Sarah: Very fair answer. What energizes you?

Will: Running with new ideas. Honestly, being able to take new ideas into reality is probably the theme in my life.

Sarah: What’s your cause?

Will: Getting to do things together. We spend more and more time on sites like Facebook, but should spend time with our friends really interacting. It could be a problem in the future. Tough Mudder’s not the only thing you can go out and do, but doing those kinds of things is important.