Why Searchers Should Never Be Afraid to Fail

Life is inherently risky. There are two kinds of risk: living outside the norm or playing by the rules. I will argue here that one will lead to a wild ride filled with high highs and low lows while the other leads to being average and miserable. Cultivating a unique view of the world—to see and understand meaning—will dictate the most important decisions in your life. I spend my summers in a magical place called Westport Harbor, right on the Massachusetts-Rhode Island border. Farms on the ocean, white sand beaches, salt ponds, and a tidal river leading into the sea are divided into the East and West forks. Last summer, I got up early with my golden retriever, Kodi, and headed over to my friend Adam’s house. He and his two golden retrievers go swimming in the West Fork every day. Adam, me and our three goldens swam upstream away from the ocean against the strong tidal current one morning. I couldn’t feel how fast the water was moving. But when we stopped to take a break, I saw the land and boats fly by. I loved it. And Kodi loved it. The water was cool and clear, with a faint green hue. I am more comfortable in the water than on land. One of my earliest memories is at summer YMCA camp with my older brother in the Berkshires. I was ten and homesick. Our counselor was a collegiate swimmer. He lined all the kids up on the lake floats one afternoon and had us race backstroke. My brother, two years my elder, was on the swim team and raced backstroke. He expected to win. I was forced to participate even though I was dreading it. I was a baseball and football kid in those days. I touched my hand to the far dock and looked up. I was certain my brother and every other kid in the race had just crushed me. “Well, there’s a new sheriff in town,” the counselor said to my great surprise, and pointed at me. I had beaten all the other kids, including my brother, my biggest rival in life, and the one against whom I measured everything. This is an experience I have had repeatedly in my life: unmerited grace. Total miracles. Moments where I honestly can’t believe what just happened. The point here is to attempt to explain the unexplainable arc of my life in hopes that you, too, will find wonder and joy and success as I have been fortunate enough to experience. I went on to become an age-group champion swimmer, but that doesn’t matter. The point of the story is the paradox. Swimming that race was the last thing I wanted to do. I loathed getting on that dock. But inside the event itself, I felt an unexpected ease, like the morning in the West Branch of the Westport River with Kodi, feeling entirely at home, swimming against a ripping tide that I didn’t even know existed. Certainly, there are times when it’s dangerous to go out into a rip tide, and the safest choice is to let the current carry you. But going against the current is a crucial part of a well-lived life, both in and outside of business. We all have the chance to encounter these transformational moments. *** The most important part of taking risks is understanding what is at stake and the importance of losing as much as possible. There are moments in life when you are going to have to go all in and bet the house. Ninety-nine percent of people can’t and won’t do that. And therein lies the difference between extraordinary outcomes and middling ones. Without the ability to see an opportunity and walk straight into what seems to everyone else like a house on fire completely unafraid, it’s hard to accomplish much that’s important. Imagine a coin flip: head, you win. What happens if you hit tails? That is the most important question there is in life. How do you feel about abject failure? Do you shy away from risk? Are you paralyzed by even the thought of losing? Everything I ever accomplished was because my only my goal has been not worrying about hitting tails but finding as many coin flips as possible. In the financial world, options have value (defined by complex mathematics I won’t bore you with). I wanted to collect as many free options as possible. If you are not afraid to lose, why not give myself the maximum opportunity to win? Most people think being bold runs the risk of catastrophe, that there is a single point of failure in life beyond which they are doomed to live in hell forever. That’s not the way life works. Unless we go to a casino and put our life savings on red, the upside from taking risk and losing is, in the long run, more productive than playing it safe to gain tiny wins that do not advance your life in any real way. In a growth mindset, “failure” accelerates improvement and the chance at long-term success. If we never fail, we never allow ourselves to become our best selves. It’s in walking into that house on fire repeatedly that greatness is possible. We can discover our deepest reserves and unusual gifts only in failure and, in that process, learn how to maximize our performance. The result of fully embodied growth mindset is zero fear. Sometimes I would reach the pivotal meeting when everything was on the line and find myself laughing out loud because I was having so much fun, while everyone else in the room looked like they wanted to puke. When your moment comes, sprint into the fucking flames with a smile on your face. This is the good part. *** I worked as a management consultant immediately after college and at Goldman Sachs as a summer associate during business school. I failed utterly at both and was shown the door quickly. That turned out to make all the difference. My parents were intellectuals—my dad an English professor and my mom a therapist—and deeply idealistic social activists. They were anti-materialistic, perhaps because of their Quaker roots and upbringing. I grew up riding in a broken-down family car and sitting on homemade furniture. We thought and talked about books. In high school, I was a loner. I spent most of my time running in the woods and dirt roads around my house in Amherst, Massachusetts. When I was 16 in 1981, I ran the Boston Marathon on a whim and finished in 2:48. Like my first experience with backstroke, my first marathon felt more like effortlessly flying than running. I don’t think there were any other high school kids in the race—certainly none from my high school. I remember being giddy afterwards because I felt like I had done something noble and cool, not because any of my classmates even knew what I had done. But I knew. It was extraordinary. I graduated from high school after my junior year to escape a home environment and public high school where I was deeply uncomfortable. Every male in my family—my grandfather, dad, uncles, and older brother on my dad’s side—had attended Princeton. I didn’t even apply. I chose Wesleyan, a school only 90 minutes’ drive away, but one that no one in my family knew anything about or had any connection to, because I met a surfer philosophy major from California whom I adored while going to a summer school program for high school kids at Milton Academy. I wanted to do things my way. For me, it was like a hero’s journey. A need to venture into the unknown, to completely rebel against my family and my past. Perhaps I was driven by rage at my parents’ non-traditional approach, my limited means as a kid, or just the need to prove that I was someone. My childhood was marked by the extreme lengths to which my parents went in pursuit of social justice, and they exposed us to those extremes. I wanted to leave all that behind and make my mark on the world ultimately in a sport none of them had ever heard of and then in the business world which was so foreign to them they would literally have no context to even understand my success. When I arrived at Wesleyan, my freshman-year roommate told me he was going to try out for the rowing team. In a family of soccer players, no one had ever rowed. So, I decided to give it a try. Rowing would become the medium through which I would imagine the rest of my life. My coach was the most important mentor I have had in my life. I finished second in the country in 1987. After graduating from college, I got a job working for a health care consulting company in New York City. I started in June and by Thanksgiving, I knew that the whole thing was not for me and quit. I lived in Boston for a couple of years, mainly drinking and getting into trouble while doing little professionally until ending up at Yale School of Management. After a series of random and long-shot maneuvers, I eventually landed a corporate finance job at The Providence Journal Company in Providence, Rhode Island — a company none of my graduating business school classmates had even heard of. The contrarian move was going to work at a backwater company in a backwater town. My facility with math and my ability to quickly understand complex financial and tax issues meant that I found myself way ahead of my boss and his boss, both of whom were twice my age. While my business school classmates were grinding it out, working 100 hours a week on menial tasks at banks or consulting firms, I got promoted to Chief Financial Officer. I was barely twenty-nine. Our company had thousands of employees and more than a hundred million dollars in profit. I convinced the board to take the 175-year-old private company public. Led our team through that process, rang the bell on the New York Stock Exchange in June 1996, at 31 years old, and less than ninety days later, had negotiated the sale of our entire company for $2 billion, twice the value of the company at the IPO. I do not doubt that others in my business school class were more talented or smarter than I; but none of them had the courage, or the stupidity, to do what I did. And just like when I decided to give the Boston Marathon a shot for the hell of it, I found myself presiding over a series of transactions that even I often wondered how the hell I had managed to pull off. I am still not sure about how exactly I succeeded, but I do know that the only way I had the chance to succeed was by swimming hard against the current while everyone else was floating with it. *** My business life over the last three decades is filled with these contrarian bets, but I want to tell you about one more—the biggest “success” of my life at least on paper—to pound the point home to you: don’t play it safe, be a lemming, or do what everyone else is doing unless you want to live a boring life. For goodness’s sake, go where no man, or woman, has ever gone before. Six months after closing the sale of The Providence Journal, I was kicking around the Back Bay of Boston with nothing to do. I was 32 and recently divorced with two little kids, so I was focused chiefly on playground time. My professional success up to that point had come at the cost of profound failure in my personal life. Based on what I had done in Providence, I had been offered numerous high-profile CFO jobs from California to Texas. I turned them all down, got sober, focused on being a more present dad, and was back in the river, swimming against the current professionally. I was determined not to do anything that would take me away from my kids. Just before Thanksgiving in 1997, I was introduced to MIT graduate Jeet Singh. Jeet and Joe Chung, his fraternity brother, founded Art Technology Group as a consulting firm to help companies establish an online presence. During this process, they had developed the first product to enable large companies to conduct e-commerce on the internet and personalize the experience. ATG was out of money when I walked in. It had been picked over by every major VC and was left for dead. Even thinking about investing was a contrarian move of massive proportions. But I liked the team, their office was a couple of blocks from my house, and I honestly had nothing better to do. I invested, gathered capital from some friends, joined the board, and became the company’s financial advisor. Eighteen months later, in July 1999, we went public. A few months later, on precisely the second anniversary of our investment, we sold shares in a secondary offering at 100x our cost basis. In February 2000, our lock-up expired, and all our shares became freely tradable. Paper wealth became real wealth. We knew there was significant short interest pressure on the stock, hedge funds anticipating a decline when insiders could sell. However, demand exceeded supply, and the shorts had to cover, causing the stock to surge. It peaked at 500x our cost basis, and everyone in our group sold at or near the top. Several years later, even after the dot-com bubble burst, the company was sold to Oracle for $1 billion. The point is that I did what no one else was willing to. When everyone else was floating downstream, I swam upstream into what they all thought were shark-infested waters. I not only lived to tell the tale, but I also got to go on one hell of a ride with my buddy Jeet. These stories sound fantastic, unbelievable perhaps. I do not believe I am extraordinary in any sense, except for my willingness to be different. To be my most authentic self. I note that material success is not all it’s cracked up to be. With the benefit of time, and a lot of suffering, I have realized that its far more rewarding to enable someone else’s success than to do it myself. But I am not going to deny that ringing the bell on the New York Stock Exchange the day PRJ opened for trading or the day our lock-up came off on ARTG and the stock soared, were not magical moments in my life. They were. And you can have experiences like them too, if you dare to listen to that deep knowing inside you that wants to explore and go for an adventure rather than playing it safe.