Failure is the Fastest Way to Success

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When I was 12 or 13 years old, I remember trying out for the 7th grade basketball team at my school. It was a private school called Roxbury Latin that began in 7th grade, so we were all relatively new there and eager to make somewhat of an impression. I was not an amazing basketball player, but I certainly felt that I was good enough to make the team.

Back then, the cuts were announced on a piece of paper on a bulletin board. I remember how upset I was to walk up to that board to find out that I had been cut from the team. I was convinced that some of the players who had made the team were just the teacher’s pets of the head coach, a young woman who taught at the school and had several of those players as mentees. And while I am a big believer in accountability, I’ll still take that story to my grave at the age of 35 because two things can be true at once.

Growing up, I loved playing sports, and I played a sport every season. Usually it was soccer in the fall, basketball in the winter, baseball in the spring, and a mix of everything in the summer. At my new school, basketball, hockey, and wrestling were the only options for winter sports. And at least before 7th grade, if I did not make a top team, there was room for me on a lesser team. This was the first time I had been cut.

My options were straightforward: I could learn how to skate and try to play hockey, I could join the wrestling team which I knew absolutely nothing about, or I could sign up for some sort of after-school study program. I decided to try out wrestling, but I was still pretty sore about the basketball thing.

My first season in wrestling was a bit of a blur and to be honest, I am not sure if I ever really understood what I was doing. But I managed to have an 11-1 record in my first year. More miraculously, I had become one of the best athletes in my class between the fall season and the spring season. In our gym classes, we would do fitness testing: pull-ups, longjumps, 50 yard dash, and other events. In the fall, I was average. By the spring, I was the strongest pound-for-pound and fastest student in the class. I imagine this is because of what wrestling did to my young body.

I will not pretend that I remained the best athlete through high school because that was not the case, and we can blame that on a growth spurt that never happened. But my accidental success in wrestling led to a passion for wrestling, and I would often joke about how lucky I was to get cut from the basketball team. I wound up having an alright career from where I came from and captained my team my senior year, and got an opportunity to continue wrestling in college.

Wrestling provided its own ups and downs. I wrote a lot in my book about how much I struggled with wrestling in college, and as much as I learned how to deal with failure through wrestling, I also failed at dealing with failure when I got to college. I struggled to present an honest version of myself and to be honest with others when it mattered most. But even through that, I learned valuable lessons that have carried on into my adult life.

For example, I worked at a startup as one of its first employees for 7.5 years. There were many ups and downs there, and countless times I thought I might give up on the journey or that we would fail (or both). But I always looked back at my failures with wrestling – including quitting the team halfway through college – as a reminder. For me, you have not truly failed at anything until you have given up. And through that lens, I was always able to will myself forward at the aforementioned startup, where we eventually had a relatively successful exit.

Many people are afraid to challenge themselves because they have a fear of failure. I know what that feels like, as I often used to shy away from the most difficult challenges myself. I shied away from writing a book, because ultimately I would love to be a writer someday, and writing a terrible book would be a lot worse than writing no book at all. But then I faced my fears and wrote a book during the pandemic, and now I am writing another one. 

The thing is, it is only through failure that you can ever have success. And quite frankly, it is only through failure that you can appreciate success. Imagine if you succeeded all the time at everything you did. Life wouldn’t be very fun. It’s why I tell mentees of mine to never fear other people, because everyone has problems. How do I know that? Because without problems to solve, our lives have no meaning. It is the same reason why you cannot enjoy life without the threat of death someday.

The faster you fail, the faster you will succeed. I often look back and wonder what my life would have been like had I made the basketball team. I would have been robbed of an opportunity to participate in a sport that really changed my life and taught me a lot about myself. I believe that wrestling gave me the competitive spirit I have today, the same competitive spirit where I willed myself to the finish line of a marathon after developing rhabdomyolysis – a potentially life-threatening condition – in its 11th mile. With that perspective, I am happy to have had that failure so early in my life. It made me tougher.

As I write this, I am preparing to travel to Tulsa, Oklahoma later this week to watch the NCAA Wrestling Tournament. I’ve been watching this tournament live for the last decade or so. I think this tournament fascinates me so much because its participants are at a level that I never could have reached myself. When you pour all of your effort into something and cannot reach the pinnacle, you certainly have a special appreciation for those that do, because you understand firsthand how much blood, sweat, and tears are involved. There are probably some who would turn away from such an opportunity; perhaps it would give them trauma of some kind to be reminded of their failure. But when you start to treat failure as an opportunity for growth, you are capable of appreciating everyone and everything.

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