by Will Dean
The whole of my first year there was spent trying to tell my parents I didn’t want to be at this kind of school, calling them up in tears. Realizing I couldn’t change their minds, I developed another strategy. I figured out pretty quickly that as I wasn’t considered one of the really smart kids, and I didn’t have an older brother, and I wasn’t from a wealthy family, the only way for me to survive was to play rugby. I wasn’t very skillful, but I was big and strong and would tackle anyone and run all day long. Off the rugby pitch I was like an in-betweener in a TV series. I wasn’t a smoker and I wasn’t a geek. It was quite a violent school, lots of fights, but I made sure I only ever had one. Told that another kid was preparing to beat me up, I squared up to him and hit him twice, hard, which unfortunately broke his front teeth. But I was never challenged again.
If I were to be asked the questions, what did you learn at school? What did you take away from that “character factory” that led to you creating Tough Mudder? I could, like anyone, give you a list of exam grades or the odd prize. I could tell you about friendships, some of them lasting, including with my eventual Tough Mudder cofounder, Guy Livingstone. But I believe the things that most make us who we are, that create one’s character, give us some grit, are often accidental or surprising, noticed by us and no one else.
In this sense, looking back now, I value just three experiences out of the five years at Oundle. The first was one of those small life lessons that changed me forever. At fourteen I had been at Oundle for nearly a year when one afternoon, a prefect, four years older than I, stopped me in the corridor and said the ten words that represented my worst nightmare: “Dean, we need you on the house debate team tonight.”
Terror in a single sentence. I had spent most of that year as the new boy in a very traditional school trying to do or say nothing that drew attention or marked me out. I pleaded with the prefect. “I actually can’t get up and talk in front of everyone,” I said, desperately. Better excuses refused to come. “I just can’t do it.”
“Dean, you’re doing it. There’s no one else.”
It is hard to explain now the sense of dread that I felt the rest of that day. The debate was in the school’s old hall, and nearly all the thousand or so boys would be there in the hope that someone might dry up or die on their feet and create that night’s entertainment. The topic of the debate was gun control. I was to speak against the motion.
When the time came—seven thirty exactly, I can still remember watching the clock—I walked out on the stage in front of the rows of expectant faces, clutching my hopeless notes, preparing for humiliation. I stood for a moment paralyzed. And then I remember starting to speak.
I have done a lot of public speaking since then and have learned to love it. But if you had told me it was something I would become capable of enjoying as I walked out onto that stage, at age fourteen, I wouldn’t have believed it possible. The moment of revelation came when suddenly, strangely, I heard coherent words and sentences come out of my mouth and start to fill the hall. I could see the faces that had been ready to laugh start to listen. I’m not going to claim the speech was a profound addition to the gun lobby argument, but it got a few laughs and a solid round of applause. And I walked off that stage and woke up the next morning feeling different, a bit bolder, changed.
There was nothing at all exceptional in that experience, of course. Facing an audience is something nearly everyone has had to do at one time or another. But still, in those few minutes onstage I’d taken to heart a lesson that I’ve tried hard to live by ever since and which was central to the creation of Tough Mudder: I had done something that was truly petrifying to me, and I had come through. I felt better as a result. I had learned one of life’s simple, crucial lessons: that by doing genuinely challenging things I could change the way I thought of myself and how others thought of me.
The second lesson I learned at school came from a math teacher, who saw something in me, singled me out for praise, moved me up to the top set, and once told my parents that in all his years of teaching he had only once or twice come across a boy as bright as me. This news came at the time as a total shock both to me and to them. It made evident that provocative research that suggests the key difference between success and failure in life is often down to a very simple fact: those people who are told that they have what it takes to succeed often do. Those who are not, more often don’t. As with the experience of standing in the hall debating, I took that teacher’s words to heart. He said I could do something special or different. I set my mind on proving him right.
The last experience that stayed with me was an incident that happened in my final year at Oundle. The school was organized on a boardinghouse system. In my prefect year, the boys in my house thought it was cool to be arrogant and rude as a group to the housekeepers. The cleaners were mocked as “skivs.” Boys would say, “Who cares if we make a mess? The skivs are going to skiv it up.” At the end of one term the cleaners complained about this rudeness and all the boys in the house were called in front of the matron, who looked after us. We stood there and she read a letter from the cleaners. It contained this line: “The only boy who treats us with any respect is William Dean, and we think he gets in trouble from the others for being kind to us.” The matron expanded on this: “William Dean is the only one that has got the balls to show any manners.”
That one sentence is perhaps the thing I am most proud of from all my time at school. Most of the cleaners in our boardinghouse were women from poor backgrounds who were working to supplement incomes. It wasn’t like I was the only kid there who understood that and what it meant. But there was a very strong peer pressure to be a snobby little shit, which I refused to join in with. I did get some stick for it. More after the matron had singled me out. “Why are you so fucking gay, Dean?” was a favorite line. But I didn’t care that much. I talk now sometimes to the Tough Mudder team about setting our own standards, about not doing the easy thing, but always trying to do the right thing. And when I do, sometimes that grim word “skivs” comes to mind.
That doesn’t seem like very much to take away from five years of expensive education, but I think those few lessons gave me some understanding that “character building” is exactly what the phrase suggests: one formative brick of a challenging experience, however small, laid on top of another. One obstacle overcome, and then the next. The important thing, it seems to me, is to find a culture in which you are encouraged to go out and look for those experiences, to see what you might be capable of.
I left Oundle with that thought firmly in mind. In my gap year between boarding school and university, rather than heading for the beaches of Australia with some friends to drink too much beer (tempting though that was), I worked for several months at a London tabloid, in a culture fueled by cynicism and cocaine, before taking myself off to travel alone in Pakistan for half a year. (I still have a photograph in which I am drinking tea outside the Osama bin Laden Barbers in Peshawar, a name that meant nothing to me then.)
It intrigues me now to think that I decided to travel in those places alone. I was happy enough in the role of outsider, but I think I was still above all restless for a sense of belonging, a place where I truly felt I fitted in. University didn’t quite satisfy that restlessness—it seemed like a means to an end—but I had high hopes of discovering that elusive feeling when I subsequently joined the British Foreign Service. I put in five challenging years working in counterterrorism—a role I took on soon after 9/11, when the Western world’s governments and intelligence agencies were desperately trying to catch up with the new global realities. In order to enter that service, I passed through a training program that tested, in particular, my psychological reserves for six intense months. I felt that I had gone into it primed for failure. Ten potential recruits are hand chosen for the elite training each year. Nine make it through. As by far the youngest and least experienced candidate—I was a twenty-three-year-old economics graduat
e up against hardened army officers and high-flying individuals with five or six years of corporate experience—I appeared destined to be the odd one out. That conviction was cemented when on the way down to my first day of training, my car was rear-ended at a junction and I got severe whiplash. In a desperate effort to overcome the discomfort, and make it through my first day, I seriously overdid the painkillers the hospital gave me. I reported for duty in what my fellow trainees subsequently described as “a state of stumbling catatonia.” The weird first impression I made on the training instructor appeared, in their eyes, and his, to have sealed my fate.
The specifics of the training are confidential, but they had evolved in the Foreign Service in the years since the Second World War to test every aspect of your determination, ingenuity, and courage under extreme pressure. Some of the training took place in Britain, some on assignment in more alien locations. Over the course of those months, despite that distinctly shaky start, I demonstrated enough of the required qualities to make sure that in the end I was not the recruit who was dropped. I then set about utilizing all that I had learned in that training, often working alone in the Middle East, tasked with creating strategies that would reveal and undermine the organization of terrorist cells.
In many ways, I found in both the challenge and camaraderie of that work the sense of purpose and belonging I had been restless for growing up. I wouldn’t say it made me fearless, but it gave me a belief that there were few things in life I couldn’t take on. I worked alongside some genuinely inspiring people who put service before personal glory. That service also, as you can imagine, came complete with lots of rules and regulations. In fact, probably way more rules and regulations than you can imagine. A few of those rules and regulations saved people’s lives. Many of them were a pain in the ass.
The Foreign Service was making noises about how, to counter the new reality of the world, it would have to be far more entrepreneurial, innovative, and flexible, which was one of the reasons I was attracted to it, and it to me. I think perhaps partly because I had never felt as though I fit into the cultures of my formative years, I had developed a very strong sense of self-reliance. I had my own ideas of how things might be done most effectively and tried to live up to standards I set for myself. Some of this made me effective in that environment. Some was viewed suspiciously. To achieve anything, you had to work around the system, and though I felt I was quite good at that, there came a point when I felt a bit suffocated by the effort. It was a hard job to leave, but when I looked around at those men and women who stayed, whose optimism had been sometimes defeated by frustration, I knew I owed it to myself to get out and at least try something different.
By this point I had developed a conviction in my mind that the surest way to find the experiences I was looking for would be by trying to create and lead a business and a culture of my own. I took my search for a sense of challenge and belonging, those two crucial components of a fulfilled life, to Harvard. I went there once again with the kind of expectations that could never honestly be satisfied. There are, as I quickly discovered, few places on earth that talk more engagingly about the value of teamwork and show less interest in it in practice. Harvard selects the most competitive individuals from five continents and requires them to compete for two years. To some degree, I was no different.
I believe we all are driven to a greater or lesser extent by the need to overturn limiting ideas of ourselves, to find opportunities to show what we are made of. Often, it is comparatively minor slights that give these feelings their sharpest edge. If I’m honest, it was probably one of those slights that led me to Harvard. At eighteen my application for a place at Oxford University was unsuccessful. There is, in Britain, still an unwritten belief to do with class and tradition (there are many unwritten beliefs to do with class and tradition) that the only university degrees that count come from Oxford or Cambridge. That’s clearly not true, but it is a perception I’ve lived with—at the Foreign Office in particular, where I was the only so-called redbrick graduate accepted on the elite program—for all my adult life. “You must have done really well at Bristol to get here” is a phrase I became very tired of hearing.
This shouldn’t have mattered to me, intellectually or socially. Having spent several years enduring the regimented life of boarding school, I was never enthralled by the idea of further education. I only applied to Bristol at the last minute after six months away traveling in Southeast Asia; still, I had thrived in my time there in a way I may not have done at Oxford. Despite all that, I’d never forgotten the sadness (and the efforts to hide that sadness) on my parents’ faces when I opened the letter saying I had been rejected by Oxford. They sacrificed a great deal for me and Oxford was the unspoken goal of that sacrifice. No one wants to feel that they have let their parents down, or not lived up to their own ambitions. The memory of that look of sadness was a big reason for me subsequently applying to Harvard—“I’ll show them”—and it was justified in one sense, in that when I was offered a place there, it was the only time I saw my dad cry with pride. If I’m honest with myself now, though, I can also see that going to an Ivy League school was a kind of vanity on my part—an expensive way of proving to myself what deep down I already knew: that most people at elite universities aren’t touched by genius or brilliance but are, generally, privileged, lucky, conscientious, and competitive. I ended up doing fine in this company, finishing as an honors student in the top 15 percent of my year. I also made some good and lasting friendships and was often inspired by the insights of my teachers. But I was no doubt hopelessly naive to go to Harvard looking for a sense of real belonging. My naïveté didn’t last much beyond the first day.
On the first morning, a professor gave us a talk about what a wonderful freethinking opportunity we had committed ourselves to and how we now belonged to a culture of inquiry like no other. Then we went around the room introducing ourselves.
The first three people happened to be three young women sitting together. And they all said, one after the other, “I’ve been working in finance in New York and I have a boyfriend in New York who also works in finance.” It was the first day, and so everyone was a little bit nervous. By the time the third girl gave the same reply, it became a bit of a joke.
The fourth introduction came from a guy sitting next to them. In an attempt to continue the joke, he said “I also worked in finance in New York and I, of course, also have a boyfriend in finance in New York.” There were a few laughs, we carried on, and I didn’t think anything more of it.
But the next day, before our first lecture, this same guy, the fourth guy in line, was standing onstage facing us. He was clearly there under duress. Unlike the day before, he was ashen and trembling a little. He went into an elaborate prepared apology about how he was ashamed of the previous day’s homophobic comments. He felt he had not only let himself down but also the institution of Harvard Business School. A professor followed these comments by declaring that Harvard was a “safe space” and homophobia would not be tolerated. The guy next to me, who became a friend, leaned across and whispered, “Is this a show trial?” It certainly looked like one. Looking around the room, I could see everyone thinking the same thing: “Forget about freedom and inquiry. I need to be pretty damn careful about what I say here because this poor guy is going to spend the two years being something of an outcast.”
One of the things people seemed to really invest time and intellectual energy in at Harvard was finding new reasons to be offended or outraged. This created a curious climate. There were serious arguments about how students should be banned from disrupting seminars by going to the restrooms, because time was money. Someone had worked out a cost analysis of how a general lack of foresight in bladder control was depriving him of so many dollars’ worth of teaching time.
No behavior went unscrutinized. Seminars lasted eighty minutes, with the last fifteen minutes of each seminar devoted to recapping what had gone before. In ce
rtain classes, such as finance, that was incredibly helpful to me because I was generally wondering what the bloody hell had been going on for the last hour. In other classes, though, I thought I had understood what was going on for the last hour. Sometimes in those classes I was in the habit of using those final fifteen minutes to read something unrelated to the class. It turned out some people were offended by this behavior. A woman behind me took a series of iPhone photographs of me reading from the wrong book so she could report me for not paying full attention in class. I was duly summoned to explain myself.
These kinds of behaviors were the direct product, it seemed to me, of a system that worked by never giving students objective marks or scores but instead ranking them against each other. Everyone at Harvard (with the possible exception of me) had gotten there by always being at the top of their class. The possibility of being near the bottom of a group and to be judged accordingly seemed to terrify people. Worse, there was never an explanation of how the rankings were made, which was at least good preparation for a corporate culture in which being in the lowest 10 or 20 percent of bottom line performers meant dismissal, regardless of your “real” effort and contribution. This attitude was clearly corrosive. It set very able people who might have achieved far more through collaboration against each other. What kind of preparation was that for life?
Outside of class, people found other arenas in which to compete. We were on average about twenty-eight years old, so the desperation to be cool hadn’t entirely disappeared. There were a lot of great individual people at Harvard, some of whom are still my close friends, but few of them were cool by the traditional metrics of what it meant to be cool—rebellion, creativity, and attitude. We were mostly nerds doing spreadsheets. We were, to my constant English surprise, students who as a matter of course applauded our lecturers at the end of every single lecture, good or bad, without question. I had hoped after the rule-bound intensity of the Foreign Office that there would be a kind of accepting, just-be-yourself spirit to college life. In fact, the peer pressure around things like drinking a lot was worse than at boarding school. I was in my late twenties by this point. I was often thinking, I don’t want to have five beers in the first fifteen minutes of getting to this bar because frankly I am a bit of an idiot when I have had five beers. At graduation, I received the “too cool for school award” because I didn’t go to enough class parties or something.