Leadership Lab: Hole in My Sidewalk

Leadership Lab: Hole in My Sidewalk
Coach Chris DePiero tries to make sense of coaches making the same mistakes again and again.

Welcome to Leadership Lab, a new weekly post from writer Chris DePiero. As you can read in his bio below, DePiero is as experienced as people get in hockey and we’re excited to give him a weekly platform to provide a hands-on approach to becoming a better leader. Every Tuesday DePiero will share knowledge, wisdom, tips and tricks that everyone from elite executives to passionate parents can learn from. Enjoy!


As a former professional coach, I have often tried to understand my particular skill set, and I cannot escape my inherent nature of being an educator. It is at the heart of who I am.

With that said, I was recently speaking with a teacher friend about the nature of how coaches at times will make the same mistake over and over again. He gave me the following short story by Portia Nelson entitled There’s a Hole in My Sidewalk: Autobiography in Five Chapters.

I walk down the street. There is a deep hole in the sidewalk. I fall in. I am lost… I am helpless.
It isn’t my fault.
It takes forever to find a way out.


I walk down the same street.
There is a deep hole in the sidewalk.
I pretend I don’t see it.
I fall in again.
I can’t believe I am in the same place.
But, it isn’t my fault.
It still takes me a long time to get out.


I walk down the same street.
There is a deep hole in the sidewalk.
I see it is there.
I still fall in. It’s a habit.
My eyes are open.
I know where I am.
It is my fault. I get out immediately.


I walk down the same street.
There is a deep hole in the sidewalk.
I walk around it.


I walk down another street.

John Wooden, the great basketball coach, liked to say “There is a choice you have to make in everything you do. So, keep in mind that in the end, the choice you make, makes you.”

We are the sum total of the choices we have made in the past. Tomorrow, we will be better (or worse) off because of the choices we make today. We may not be perfect, but we can make progress each and every day. Similarly, those around us may not be perfect but we can encourage, uplift, and empower them to be their best.

What will we do today to be better? What will we do today to help others be better? What will our journey look like? What choices will we make along the way?


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Chris De Piero

Chris is a Senior High-Performance Coach and has spent the past 30+ years in the game of hockey as a player, Head Coach, General Manager, scout, mentor, consultant and most importantly as a parent. He has done so in the NHL, with Hockey Canada, in the OHL and the OHA, as well as European pro hockey. In addition, he has spent 15+ years as a classroom teacher as well as being in leadership positions as an administrator with a private high school in Toronto.

Chris has coached over 100 players who have played and/or been drafted into the NHL, and 100+ players who have gone on to play NCAA or USport hockey. He has won multiple championships as a Head Coach and GM, notably winning a Stanley Cup ring from being a member of the scouting staff of the Pittsburgh Penguins from 2012-2016.

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