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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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We’re taught that if we just try harder, we’ll succeed—and that virtue lies in the trying. But what if that’s not only wrong, but harmful?
In this episode, we examine the myth of willpower as a moral virtue, and the emotional collapse that follows when effort alone doesn’t work. Whether it's in the lodge or in life, perseverance is not always the solution. Sometimes, it’s the trap.
Real growth doesn’t glorify exhaustion. It recognizes that change requires structure, support, compassion—and more than just will.
🔑 Key Takeaways
- Willpower alone is unreliable and unsustainable over time
- Struggle isn’t always virtuous—especially when alternatives exist
- Real transformation honors effort and systems that support change
💬 Featured Quotes
“Willpower is the idea that through determination alone you can overcome the obstacles ahead of you.” [00:00:09]“In a lot of settings, there’s no merit in that whatsoever.” [00:00:48]
“The moment you’re low on dopamine or serotonin, you violate your own precepts.” [00:01:24]
“And then you go and consider that a moral failing—which happens to everyone.” [00:01:36]
🔗 Explore Related Episodes
- “The Gavel and the Gap: When Self-Improvement Gets Real”
→ Explores how effort meets resistance—and why transformation demands more than force. - “Fixing the Wrong Thing: The First Trap of Transformation”
→ Looks at the risk of misidentifying struggle as productive when it may be misdirected. - “Yin and Yang in the Mortar: What Compassion Teaches the Builder”
→ A reflection on care, support, and knowing when softness—not pressure—is the work.
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