How Wrestling Taught Me the Invaluable Lesson of Dealing With Failure

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I came into the sport of wrestling by mistake. I had always played basketball for a winter sport growing up, and I had aspirations to make the basketball team when I started going to private school in 7th grade. If New England as a region is known for producing athletes in any sport, it is certain that hockey and basketball are amongst them. This leaves wrestling as the region’s ugly stepchild as far as winter sports go – reserved for the worst of the athletes who were not good enough to make their respective hockey or basketball teams.


I was one of those unfortunate people. I remember how disappointed I was to see the cuts on the bulletin board and the revelation that I now had to find something else to do with my time. It all seemed very unfair to me at the time, and since I did not know how to skate, it left wrestling as my only option for a new hobby to take up that season. I did not even know that wrestling existed until then, and frankly, I wasn’t very excited about it. After all, it was only the unathletic losers who were forced to do wrestling, or so I thought.


I spent most of my time in wrestling practices being confused about what was going on and just trying to make it through the season. My first ever match was at Providence Country Day. I walked out to the mat, not really sure if I had retained any of the moves in my head, just hoping for the best or that I would not embarrass myself. I thumped my opponent (somehow), realizing for the first time that maybe this wrestling stuff was not so bad after all. I ended up going 11-1 that season, my only loss coming in the finals of a tournament to a much more experienced opponent. Before the season had started, I was a middle of the pack athlete in gym class fitness testing. Once the season was over, I had the fastest 50 yard dash, I could do the most pushups, and I could jump further than anyone else in my class. In light of all of this, I decided to dedicate myself to being good at wrestling. It was the first time that I felt like I was in control of my own destiny, and I liked winning.


Within the confines of New England prep wrestling, I had a relatively good career. I started on the Varsity for four seasons and was elected co-Captain my senior year. I spent most of that season ranked #2 in all of New England, and after an unfortunate late season injury, I slid to what for me was a disappointing 6th place finish and a performance at the national tournament that did not meet my own expectations. Still, this was a relatively good career for where I came from. I was never close to being the best, and along the way, I was forced to come to grips with those shortcomings to push myself harder and harder. I never gave up while all at once forgiving myself for being human.


Phone calls started coming in from college coaches as my career was ending. These were mostly from small, local Division 3 schools I was not interested in going to anyway. A couple were interesting, including Williams College, which was very much on my list. I ended up doing a visit there and enjoyed it. But coming from a very competitive academic environment, my foremost priority was just to find the college I wanted to go to and try to get in there. If that school had a wrestling program and would let me continue wrestling, even better.

So when I showed up at Princeton to do a college tour, I called the coach out of the blue and asked him if I could come and introduce myself. I walked down to his office and did just that. He had no idea who I was because I was not even remotely on his radar, and rightfully so. New England wrestling is not very good in the grand scheme of things as compared to other places, and moreover, I was not particularly dominant anyhow. I said I was a hard worker and wanted to learn as much as possible, which was true. And the coach was very nice to me, encouraged me to apply to the university, and said he would be happy to let me practice with the team if I got in on my own merits.


I was very fortunate to find out months later that I was accepted into Princeton. The wrestling program underwent some change immediately thereafter, bringing in a new coach in an attempt to revive the program. A decade prior, the program had been disbanded due to Title IX, but the alumni organization swiftly stepped in to provide the funds to bring it back. In my freshman class, only one other wrestler was a true recruit. The idea was that the new coach would step up the recruiting with the university’s cooperation and bring a new mentality to a program that had been the doormat of the Ivies for a little while. He has done exactly that, but we’ll get to that later.


As freshman year began, so did my college wrestling career. Within two weeks of training, the one recruit in our class quit the team. He was roughly my size, so this immediately thrust me into the starting lineup. My plan when joining the team was just to work hard and maybe be good enough by my senior year to help the team. Those plans changed right away.


Strictly from a training perspective, every part of my college wrestling experience was a wake-up call. In a nutshell, it was several orders of magnitude more difficult. In some ways, I started to resent my high school coach and teammates for not pushing me harder. Obviously those feelings were unfounded, but I immediately felt regret that I had not started the sport sooner, done more camps, and worked harder. I had always thought that I was very determined and a hard worker, but the effort in college was so much more demanding that it really just made me feel like a fraud.


Wrestling in college was the hardest thing I have ever done, by far. Being disciplined about making weight, being disciplined about working out in a very deliberate fashion twice a day, and seeing little success was incredibly challenging for me. Our coach would say that Princeton wrestlers were the toughest in the country because of the demands they had from a wrestling standpoint while also dealing with the intense academic pressures of being a student at Princeton. I believed him back then and I still believe that today.


I ended up wrestling on the team for almost two seasons, and I never won a match. Some of my opponents were future Olympians, like Frank Molinaro of Penn State, and many of them were All-Americans. Succinctly, I was always punching out of my weight class. It was never easy, and it wore on me. But I was proud to be challenging myself. And even though I did not get the results that I wanted, it calloused my mind in a way that was life-changing. I learned more technique in those seasons than I did in all of the seasons I spent wrestling beforehand, and I still use many of them today when training Brazilian Jiu-Jitsu. As Dan Gable once said, “Once you’ve wrestled, everything else in life is easy.” And that mantra has proven to be true for just about anything. When I am having a really tough workout, I always tell myself that it’s not even close to as hard as what I did in college. When I am having a really tough day, I tell myself it’s not as tough as those times. Nothing can stack up to how hard that was for me because as I already said, it was the hardest thing I have ever done by far.


Deciding to leave the team was a painful moment for me. The coach told me I would regret it, and I remember feeling at the time that that was funny because of how hard it was. And while it probably was the right decision for me at that time, it does not change the fact that I think about it almost every single day. It drives almost every single thing that I do. What I realized in that experience is that quitting at something does not sit well with me. Even if it is something incredibly difficult that 99.9% of people choose not to do – like wrestling for a college D1 program – if I start it, I want to finish it.


One of the best chapters of the book “Think and Grow Rich,” is a story about the man who almost struck gold. As you can probably guess, it is about a gold miner who gives up on his job when he is one strike away from striking gold and changing his life forever. That resonated with me because when you are the man who almost struck gold, you have no way of realizing it. When I liken that to my own experience, it makes me wonder: how close was I to starting to realize the fruits of my labor, and how would that have impacted my decision and my life? When I was a teenager, I lacked a critical toughness because I had had no watershed moment of dealing with adversity. In retrospect, I was relatively fortunate and was not hardened as a result. Questioning myself and pushing myself for what seemed like every waking second of nearly two seasons was the greatest challenge for me at that time, and wondering “What if?” has made me realize that I never want to ask that question ever again. And in many ways, I did feel like a man who almost struck gold, because once I quit the team, we forfeited my weight in the team’s next match to an opponent I had defeated three times in my senior year of high school.


That realization has set in for me in many facets of my everyday life. I was an early employee at a tech startup and things have not always been easy there. Especially in the early days when we faced a myriad of issues that never seemed to go away, and with other employers coming to me and promising me what they perceived to be much better opportunities, I must have thought about quitting at least 100 different times. And even in moments where it felt obvious to me and any objective observer that that was what I should do, I could never bring myself to do it. “What if,” I asked myself, “I am the man who almost struck gold?” I did not want to have another moment of my life where I looked back with unanswered questions about what could have been or who I was. And while I would not say that my company has yet reached the proverbial finish line where I would say that the entire venture was what I wanted it to be, I am having unparalleled success in my role, with great autonomy and impact on the organization, and I get to work with the best and brightest people on the planet, several of whom are actually Princeton wrestlers. It goes without saying that I know firsthand what they are capable of and admire them for being able to finish a job that I could not finish.


The lessons learned from failure extend to other areas of my life. I was a terrible student in Brazilian Jiu-Jitsu when I first got started and found myself making the same kinds of excuses for myself that I had made in college. Things like, “I have other hobbies besides this,” for example, as some sort of rationale for why I did not need to be great. Many times I thought about quitting, assuming I could never be great for very practical reasons, like my lack of flexibility. Jiu-Jitsu requires a lot of deliberate attention to detail and practice and leaves less doors open for natural athletes like the sport of wrestling does. I made an intentional decision recently to buckle down and focus on my training, and the result was that I finally got promoted to blue belt. I now have new goals to compete this year, plan my training (I often used work travel as a reason to be not training regularly), and hopefully get promoted to purple belt a lot faster than it took me to get to blue.


Where I am going with this is pretty simple – the experience helped me to redefine what “failure” means. I don’t regret giving it my all and not getting the result I wanted. I don’t look at falling short as failure. I look at giving up as failure. Contextualizing things this way allows me to re-focus difficult times to give the extra push I need to reach the finish line. It’s OK to not always be the best, as long as we are constantly giving our all and not giving in.


Whenever I think about giving up at anything large or small – a work problem, a friendship or relationship challenge, an athletic endeavor – I think twice. Is the pain I am feeling now a temporary pain? How will I feel if I can overcome it, and how will I feel if I do not? Most importantly, how will I feel if I at least try to overcome it and fall short versus just giving up? I can’t say that I am the best salesperson, the best grappler, or the best human being, but it sure feels a lot better knowing that I am trying my best at every single thing I do. What’s more motivation is that Princeton now has one of the best teams in the country. The same coach took arguably the worst team in Division 1 wrestling, a group of students who just happened to want to try wrestling, and has entirely changed the culture to the polar opposite. Watching that from afar, it is hard to make excuses for myself any more. It certainly feels a lot better not to.

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