The Paradox of Winning and Success

A paradox:

“Winning is the most important thing in my life, after breathing. Breathing first, winning next.”

– George Steinbrenner, 7-Time World Champion Yankee Owner

“Competing at the highest level is not about winning. It’s about preparation, courage, understanding and nurturing your people, and heart. Winning is the result.”

– Joe Torre, 4-Time World Champion Yankee Manager


Another paradox, just to hammer it home:

“The person that said winning isn’t everything, never won anything.”

– Mia Hamm, 2-Time World Cup Winner, 2-Time Olympic Gold Medalist

“There are more important things in life than winning or losing a game.”

– Lionel Messi, 9 La Liga titles, 4 UEFA Champions League titles and 6 Copas del Rey


And finally, some insights that shed light on a potential solution:

“Success is peace of mind, which is a direct result of self-satisfaction in knowing you made the effort to do your best to become the best that you are capable of becoming.”

– John Wooden, 10-Time NCAA Champion UCLA Basketball Coach

“Life is about choice. The choices we make in life, dictate the lives we lead. To see our athletes work so hard at gymnastics, then put their heart and soul into performance and then get a score and be told if they’ve won or lost is something I hope I never get used to. It really goes against my grain (although I can tend to get caught up in it during competition). At the end of the day, the reward and validation of success needs to come from within, knowing we had prepared and performed to our best ability regardless of the score.”

– Valorie Kondos Field, 7-Time NCAA Champion UCLA Gymnastics Coach


The past couple weeks, I’ve been working on my relationship to success and winning and what role I want them to play in my life. 

I constantly run into this pervasive idea that unless I’m striving and pushing myself to get better, there’s no way that I can grow and improve. Acting from a place of joy is fine if you’re just dabbling in an activity.

But if you really want to grow and improve, you need to be hungry for that external goal of winning. (You gotta be crazy. You gotta have a real need). You need to be willing to win at any cost.

Oh, and if you’re not hungry enough, baby, get angry at yourself. Because if you’re not hungry, you can’t win, which means you’re a loser, which is obviously not acceptable.


Anger and frustration can certainly be incredibly powerful sources of energy, particularly when I’m in a place of apathy. I’m certainly not saying people shouldn’t get angry. Your feelings are always valid.

I’ve found, however, that the cost of relying on them as a primary, go-to energy source over an extended period of time is extremely high. And I’m not talking about the cost of persevering and working hard and being disciplined.

Anger and frustration are a bit like coal. They are dependable and they can help me get my task done.

However, like coal, anger and frustration produces pollution that adds up over time. I internalize the idea that if things aren’t going the way I want them to, it’s because I’m not good enough. Others see this, and they too internalize the idea that if things aren’t going well for them, it’s because they’re not good enough. By acting out of anger and frustration over an extended period of time, I harm both myself and those I interact with in my life.


Joy and love, on the other hand, are much more powerful sources of energy. They produce benefits to myself and all the people I interact with in my life that compound over time, creating more benefits in the future.

A small, concrete example: last year I share Finding Mastery, one of my favorite podcasts, with a couple of my good friends. Just last week, they lent me their copy of the book Rebound which is giving me fantastic insights into how I want to work as a personal trainer. They discovered Rebound by listening to an episode of the Finding Mastery podcast featuring the book’s author, Peter Park. It was an episode I had missed and would not have found on my own.

I didn’t share the podcast with my friends to get any sort of external benefit. I just enjoyed it and thought they would too! That’s part of the power of acting out of joy. It helps you and everyone around you in ways the calculating mind doesn’t anticipate.

And just to dispel the myths, you can win joy as a core value – Steve Kerr and the Warriors certainly do a whole lot of it.


You can achieve great things in the material world with either source of energy. The examples I shared at the beginning are just a handful of the countless models of success that exist in the world.

I could explore the common patterns that lead to material success, but I feel that’s a topic for another day.

For today, I’d rather ask you, reader, why do you seek achievement? Why do you seek greatness? Why do you seek success? What is it that you hope to gain by winning? What cost are you willing to pay for it?

Coach Wooden said that success is peace of mind. As I’ve become more aware of how my actions impact my own life and the lives of those around me, it’s become clear that there is nothing I can achieve, no greatness to be attained, no material success—no matter how noble the intent—that in and of itself will give me lasting peace of mind.

Instead, I’ve found that it’s not about what I do, what I achieve, what I win, but how I do it. And the best part? You get to choose your own path!

  • What type of life do I choose to lead?
  • Do I choose to build myself up or tear myself down?
  • Do my actions better the lives of those around me?
  • Do I choose to do my best?
  • How do I choose to move through the world?

As for me, I choose to spread joy. I choose to spread kindness. I choose to spread love. How about you?

Article Name
The Paradox of Winning and Success
Exploring the paradox of winning and success and proposing joy as a potential path forward.

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