3 Lessons that Coaching Wrestling Taught Me About Being an Entrepreneur

“Sport has the power to change the world” — Nelson Mandela

Sport is a powerful metaphor for life. From Vince Lombardi to Billy Jean King, their wisdom transcends sport itself and provides insight into our everyday lives. This autumn, sport became an instructive metaphor for my life, too. After 23 years of working in the corporate world, I launched a start-up business and experienced the immediate emotional peaks and valleys of becoming an entrepreneur. There was the exhilaration of starting a new adventure as a forty-something-year-old, and the anxiety-filled moments that ensued when I let go of the corporate safety blanket. And as I launched into this journey, I was in need of inspiration.

Little did I know that inspiration would arrive in the form of 35 grade school boys. Several weeks before this watershed career decision, I was asked to volunteer as the head coach for a local youth wrestling program. Knowing what lay ahead in terms of the time commitment, I was reluctant to accept. Nevertheless, I accepted and three months later, the lessons that the children taught me far exceeded what I was able to teach them. Each week, I discovered something new. Children, in their unvarnished sincerity, provided great wisdom and served as an every-day muse for the challenges of launching a start-up business. Now, with the wrestling season coming to a conclusion, I picked out three lessons that I learned from them over the course of the season that has guided me as an entrepreneur.

1. Seeing it Through Beginners Eyes

“Even the greatest was once a beginner. Don’t be afraid to take that first step.”

– Muhammad Ali

It is hard to be a beginner. When something is completely new, we can easily be overwhelmed by the abundance of new information. Simply put, it’s intimidating. And it’s one of the cardinal reasons why adults avoid trying new things. As a coach, I was confident and experienced, having coached years before at a higher level. But these young boys were not experienced. In fact, most of them had never seen a wrestling match, let alone participated in one. At the outset, some of the boys struggled with learning new and complicated rules and unfamiliar movements. And sometimes there was tears and frustration. But there was also extraordinary resilience. More often than not, the boys pushed aside their fear of learning something complicated and new, asked for help when they needed it and tried again if it didn’t work out. This simple, yet brave approach, was an important reminder to never forget what it’s like to be a beginner. When I first envisioned launching my business, I assumed that I had to get everything right the first time. Failure was not an option and imperfection was unacceptable. The uncertainty of never having run a business felt paralyzing and I was embarrassed to ask for help at the start. But it was the beginner’s mindset that these children modeled to me and inspired me to embrace being a beginner all over again. By looking through a beginner’s lens, it reminded me that it’s OK to dare to try something new and for it to not work out perfectly. It’s the foundation of learning any new craft.

2. Preparation for Opportunity

“It’s not the will to win that matters — everyone has that. It’s the will to prepare to win that matters.” — Paul “Bear” Bryant

The difference between winning and losing comes down to readiness. In wrestling, preparation is everything. If you don’t consistently practice and test new things, the risk of making a big mistake in a live match markedly increases. Most people assume that the most gifted athlete is the one who is going to dominate. But in fact, I found that the boys who consistently practiced hard and tested out new ways of doing things were the ones who enjoyed the most success. Entrepreneurship follows a similar coda. While many people perceive start-up entrepreneurs as gunslingers, shooting from the hip on every decision, it turns out to be quite the opposite. The successful entrepreneurs that I interviewed as I have gone on this journey, share the common trait of rigorously and deliberately practicing and trying out new ways of doing things. And similar to the little grapplers, its not necessarily the most naturally gifted entrepreneurs who thrive, it’s the ones who consistently show-up, prepare and show true grit.

3. Daring Greatly

“A Champion is Someone Who Picks Himself Up When He Can’t”

- Jack Dempsey

Watching a little wrestler walk alone to the center of the mat is awe-inspiring. In particular, the story of one young guy sticks in my mind. He was smaller, slower and less skilled than his opponent. And the young wrestler was mercilessly dominated in his first bout. It was painful as a coach to stand in his corner, helplessly barking advice, while he struggled. He was pinned unceremoniously in the 2nd period of the bout and tears of emotional and physical pain streamed down his cheeks. He declared that he wouldn’t wrestle another match that day. But after some words of encouragement, this 6-year-old boy decided to give it another try. And when his match was announced, he once again walked alone to the center of the mat and battled for the entire match. In the end, he lost a nail-biting, 1-point match. But this time there were no tears. Only a handshake and a smile acknowledging, despite the defeat, that he tried his best. This small act of bravery is burned into my consciousness. Only days before, I was stung by multiple work-related defeats. I gave the very best that I had and discovered that it wasn’t enough to win a project. Even as an adult, it is not easy to cope with failure. I began to question my resolve and my decision to start a business. But on that Sunday morning, I was reminded by that little boy that it matters little if you get knocked down. It’s whether you pick yourself up and carry on that matters.

Sports create powerful metaphors because they are vivid capsules of life. They not only entertain and inspire us, but if we are open-minded and alert, they can instruct us. Coaching a group of youth wrestlers hardly seems like the proving grounds for a nascent start-up entrepreneur. But when I looked closely, I found that the most important life and business lessons were lurking inside the minds and bodies of these little athletes, just waiting to impart their wisdom and guide me on my bold, new adventure.

Dan is the Founder of Deliberate Innovation, led Worldwide Innovation at Pfizer and is a contributing writer for multiple journals on Innovation & Creativity.

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