Serena Taught Me: 3 Lessons I've Learned from Witnessing Greatness

Breaking down the lessons I've learned from watching Serena Williams' illustrious career.

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Unless you’ve been living under a rock, you know that Serena evolved away from tennis, playing her last match on Friday, September 2nd. I had dinner plans that could not be rescheduled, so I sat in the restaurant, airpod in one ear and eyes conspicuously trained on the cell phone in my hand.  Eventually, friends noticed I was not locked in on our conversation and asked what I was looking at… “history”...was my response.  Watching Serena play her last match and approach the final week of her legend-inducing career, got me thinking about the first time I watched her play the game she loved; the parallels I drew to her story, and how rooting for her helped me, and millions of little girls who looked like me, root for myself.

In today’s newsletter, I’m going to share 3 things I’ve learned from watching Serena Williams for the last 27 years and how it helped shape how I approach business.

When I say “shaped”, I don’t mean inspired me somewhat, I mean completely redirected how I approached business and became part of my guiding principles.

Blaze your own path 

Serena’s path to tennis greatness was not an easy one. She has always danced to the beat of her own drum and has never conformed to anyone else’s expectations.  Whether it was blazing onto the path wearing white beads on her head, exalting on a 115 mph serve, or embracing her muscular physique, Serena never back down from showing up as her full self and always embraced the path she walked.

Pivot & Adapt

The only thing guaranteed in life is change and Serena was built for it. From hard clay courts to fast grass to rainy days and blazing heat, Serena’s 858 career wins, leading the way for 24 grand slam titles, showed that she could win in any climate.  Her versatility on the court and ability to perform under pressure helped her build a reputation as both a fierce competitor and one who was incredibly hard to beat through the years, but I think the greatest lesson here is how Serena’s career is filled with different eras of play all based around how she changed her game.

The Serena Effect permeated across players and moments, locked in my memory throughout very specific times in her career.  In 1999 when she was the youngest to win and again in 2013 when she was the oldest to do it. 

 Never Stop Competing

Serena has had more winning years throughout her career than she has lost.  Showing everyone that winning was at the core of who she is and what she does.  Last Friday’s stand on the court as she took her final bow showed just that.  Serena wasn’t supposed to make it out of Match 1.  This was evident in the ceremony planned shortly after the match.  Again, on display in Match 2 of the US Open.  Serena kept winning because she kept showing up.  She dug deep and pulled out just one more serve here or a well-calculated set there and suddenly – those efforts compounded until they didn’t.

 "I am lucky that whatever fear I have inside me,
my desire to win is always stronger."

- Serena Williams

Being an entrepreneur is something that you don’t do if you can do anything else. It’s the thing you do because the idea of not doing it keeps you up at night; because your desire to win is stronger than anything else you have inside of you, and it’s the thing you do when you’ve tried too long to fit yourself into boxes that were never meant for you.

Entrepreneurship takes a lot of discipline, an unwillingness to quit, and an almost relentless drive to achieve what others before you have not.  Watching Serena’s approach to the game helped to shape the way I approach my chosen sport and I am forever grateful for her contributions.


See you again next week.

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