Holiday: Every Retired Pro Athlete Regrets Not Enjoying Playing More
Ryan Holiday · How To Build Self-Discipline For 2026 (5 Step Routine) | Ryan Holiday · Dec 31, 2025 · at 22:14
Ryan Holiday illustrates the pitfalls of outcome-dependent happiness by referencing his conversations with retired professional athletes.
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“There's not a single athlete That you've, you will ever talk to who's retired, who doesn't say something like, I wish I enjoyed playing more, because at some point it just goes away, and then at that point the winning and losing stops mattering, and all they think back is like, I was in the NBA, and I was miserable because of winning or losing, instead of being able to just be grateful that I get to play professional basketball.”
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