“Chips on Shoulders, Leads to Chips in Pockets”: The Rage to Compete

I love that Josh Wolfe quote. No one exemplifies this more than Michael Jordan. Just watch this Michael Jordan acceptance speech at the Hall of Fame Enshrinement. 

https://www.youtube.com/watch?v=XLzBMGXfK4c

He calls out the player who made it over him in high school basketball. He calls out Coach Leroy who picked someone over him. He had so many people who rejected or put him down which turned into that competitive will to win. I see that rage and fire was what drove him. 

Not sure if we should admire this or feel bad for him. But he said “He Just wanted to Win” and did he ever! This is why he is one of the greats. Leading the Chicago Bulls to multiple championships and now as billionaire businessman worth $1.7B as of 2022. 

I’ve also noticed that all of my best founders and everyone I know who are super successful in what they do, whether in investing, academia, arts, business and sports all share this trait. A massive chip on their shoulder and lots to prove which translate into a crazy good work ethic and competitive drive. 

I’ve spoken about the things that drive me. My rage when I see stupid things or unfair things. Or probably mainly about proving myself versus the folks who talked down to me when I was growing up. And even frankly when I was starting my career here in Silicon Valley. Anger at perceived disrespect. I still feel this way after 22+ years here, 450+ investments, hopefully a decent track record as an operator and investor. Somewhat known in the industry. Yet I still feel like an outsider with much to prove. 

Not sure this is a good thing. Speaking with my therapist, I admit it’s been great for my career & business in general as I’ve done alright. But in family life and for my own personal internal peace, this is a terrible thing. 

It’s like you have a tool or tactic that has worked so well for you in the past but due to different circumstances it is no longer useful. Yet you have a hard time letting go or dropping it. I find myself in this situation now. I know it no longer serves me, yet I am still trapped in this loop. 

I think we all have found ourselves in this situation. I’m learning to channel this rage and chip on my shoulder into my health. I’m learning to let go. I’m learning to forgive myself and others. I probably saw more into the situation than they did or had meant. Ultimately I’m learning how to step back and on trying (stress on “try”) not take everything so personally. 

I just need to be grateful and to focus on the bigger picture. That and executing against my big priorities with the big goals of a strong family, building out my portfolio businesses and having a positive impact in the world. The rest will take care of itself.