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Episode 103: Winning Ugly: Mental Warfare in Tennis by Brad Gilbert - What If I Didn't Care About the Outcome?

Author
Chris Sears and Trieu Nguyen
Published
Fri 08 Aug 2025
Episode Link
https://www.clubany.org/post/book-103-a-year-of-magical-learning

Discussion Topic: What would it be like if I stopped caring about winning or losing?

Book Title: Winning Ugly: Mental Warfare in Tennis—Lessons from a Master by Brad Gilbert.

In this insightful episode, we delve into the powerful lessons from Brad Gilbert’s book 'Winning Ugly.' We explore the journey of understanding the essence of competition and the importance of focusing on values over outcomes. Our discussion includes insights on balancing the drive to win with the joy of the game, the impact of mental acuity in sports, and personal reflections on letting go of results. Join us as we navigate the intricate dynamics of the 'rider' and 'elephant' in our minds and how they influence our actions both on and off the tennis court.

00:00 Introduction and Episode Overview

00:15 Brad Gilbert's Journey and Winning Ugly

00:56 Mental Warfare in Tennis

02:16 Personal Reflections on Winning and Losing

04:01 Balancing Competitiveness and Enjoyment

10:25 System One vs. System Two

22:29 The Pitfalls of Achieving Ultimate Success

22:55 Living Your Purpose Through Values

25:03 The Meaning Behind Meaningful Work

26:31 Aligning Actions with Values

29:31 The Dangers of Goal-Driven Happiness

30:33 Embracing the Journey Over the Destination

33:53 The Importance of Enjoying the Process

42:00 Final Thoughts on Values and Purpose


Read the reflection: What would it be like if I stopped caring about winning or losing?

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