What Basketball Taught Me About Failure, and Why I’m Thankful Today
Sports have the power to spark immense joy and crush you. It’s been ten years since I played college basketball and I still think about this a lot. I recall my favorite memories fondly and cringe at the painful ones. Since my playing days ended, I’ve started new life chapters, personally and professionally. With time and reflection, I’m now more convinced than ever that the following is true: the most important lesson I learned from playing basketball was how to fail.
Sports Can Be Cruel
Let’s start with my favorite time of the year — March Madness. Every year offers high drama, inspirational upsets, and my favorite moment in sports: buzzer beaters. I vividly remember Tyus Edney’s full-court dash to lead UCLA past Missouri, Kris Jenkin’s heave for Villanova, and of course, Christian Laettner. 27 years have passed since Laettner’s iconic shot, and yet for most of us, just hearing his name immediately brings us back to his game-winning shot against Kentucky.
For the heroes of the game and their fans, these moments represent pure joy. For the losing side, those buzzer-beaters are utterly deflating. Imagine being on the receiving end of the Laettner shot: your team of underdogs had played a near-perfect 39.92 minutes of basketball. You’d earned this win. How terrible would it feel to know you were so close to realizing a dream, only to have it taken away in 0.08 seconds.
The reality is sports can be cruel — just ask Chris Webber — and the cruelty of failure is something every athlete will experience at some point. But failure is also something every athlete should be thankful for.
Learning How To Fail
My first real taste of failure happened after I arrived on Stanford’s campus in the summer of 2004. Up until that point, I’d had a storybook experience playing basketball. My high school coach was incredibly supportive, my teammates had become lifelong friends, we’d won a state championship (the first in our small school’s history!), and I was offered a scholarship to my dream college. I had worked hard and naturally assumed this trajectory would continue in college and eventually even take me to the NBA. Then, things got bumpy.
The head coach who recruited me left to join the Golden State Warriors, which meant an adjustment to a new coach and system. I faced tougher competition than ever before, and excelling at the college level was more challenging than I’d anticipated. Additionally, I accumulated a series of knee, back, and foot injuries that slowed my development and on-court performance, culminating in a fractured knee during my junior year.
I wish I could tell you that I responded perfectly to all of these setbacks, but the truth is that my response varied. I bounced back admirably from some and struggled with others. The end result was my collegiate basketball career didn’t play out the way I’d envisioned, and I didn’t make it to the NBA. This caused me to ask myself, was my basketball career a failure?
I often think about something my college coach Eric Reveno told me during a particularly hard drill: “If it was easy, everyone would do it.” Even though I may have seen my basketball career as a failure at the time, I now know it wasn’t.
Taking Challenges Head On (Over Coffee)
After college I worked as a speechwriter, an investment banker, and for the past seven years in software sales at high-growth startups. I didn’t realize the value of basketball’s lessons until a few years into my career during a casual coffee chat with a mentor.
At the time, I was working in sales at a technology “unicorn”, and the company was growing at an astounding rate. I was lucky to have joined this rocket ship for my first job in tech and benefited greatly from my experience there.
About a year into my tenure, there was an organizational shift that prolonged my timeline for a promotion. Deeply frustrated by this, I vented to my mentor over coffee. I complained that the restructure was a mistake, explained why I thought I deserved the promotion, and ultimately commented on how “messy” things felt. My mentor listened patiently, smiled, and said: “Wherever you work things will be messy and people will make mistakes. The important question is, how will you respond, and how will you make things better?”
What began as a mundane coffee turned into an important moment in my career trajectory. The challenge my mentor issued was direct and unapologetic, and I had the option to either disregard it or step up. I reflected on my most difficult tests in basketball: coaching changes, adjusting to better competition, and fracturing my knee. I thought about how I responded to each challenge, and the times I was most proud of were when I kept my focus and met the challenge head-on. I thought back to Coach Reveno’s mantra of “If it was easy, everyone would do it.” Then, the lessons basketball taught me kicked in.
I knew what I had to do. Instead of letting this setback and my own frustration negatively affect my own efforts, I doubled down on my work until I got that promotion. I could have just as easily disregarded my mentor’s advice, blamed my problems on something else, and ultimately rejected necessary change. Ultimately, we all have to come to terms with failure and our responses will meaningfully define the trajectory of our lives. These lessons have stayed with me throughout my career and have helped me go from being a top performing sales rep to leading different sales teams at Intercom, another tech “unicorn” that I currently work for.
Resilience Is A Success Multiplier
I won’t pretend that I’m at peace with failing. Whether it’s a shot I miss in a pickup game or a sales deal we lose, the competitor in me will always bristle. However, with time and introspection, I try to recognize failures for what they are and take from them what I need to. There’s knowledge in every miss, and there’s always a lesson that can be incorporated into future efforts. Resilience is a lesson basketball taught me, and one of the most important teachings I hope to pass onto my son.
Everyone fails. The most ambitious, successful, and accomplished humans in the world — Michael Jordan, Steve Jobs, Serena Williams, and Barack Obama — have each failed at something. Why would we hold ourselves to a different standard? In sports and in life, we’re trained to project the strongest and best version of ourselves. This is a shame, because failure is a universal part of the human experience and shouldn’t be a dirty word. In the words of Alexander Pope, “To err is to be human,” and by stigmatizing failure we increase our fear of it to our own detriment.
Now that I lead sales account manager teams at Intercom, one of the things I look for when hiring a candidate is, how will she or he respond to adversity? There are a lot of characteristics that contribute to professional success: grit, resilience, and a growth-mindset. Most of these boil down to the question, “How do you respond to failure?”
Looking back on my basketball career, I could ask myself the same questions. Did I fail to reach my goal of being in the NBA? Yes. Was my basketball career a failure? Unequivocally “no.” Basketball taught me how to face my challenges head on, overcome adversity, and maintain focus despite chaotic circumstances. The lessons basketball taught me about failure have become a success multiplier in my personal and professional life, and for that I’m truly thankful.
What’s something sports taught you about responding to failure, and how has that impacted your life? I’d love to learn from your stories. Share them below or email me here.
This piece originally ran on the Coin Flyp, a company dedicated to telling the stories of athletes’ transitioning into the professional world.
