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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 challenge the myth that midlife means getting serious and losing wonder, and show how curiosity, awe, playfulness, and childlike fearlessness become fuel for resilience, creativity, and even longevity. Practical tools—NLP anchoring, the Wonder List, and a six-step review—turn inspiration into action at home, at work, and in relationships.
• why life feels flat when outcomes outrun experiences
• awe as a nervous system reset that primes learning
• lightness as a leadership choice in tense moments
• flexibility versus rigidity in midlife habits
• safe exhilaration for growth without recklessness
• NLP anchoring to recall joy on demand
• Wonder List to re-sensitize attention and delight
• gendered traps of outcome chasing and over-functioning
• reviving curiosity to renew intimacy and connection
• six-step review to identify strengths, drop labels, and plan playful risks
• play personalities and planning a play date with yourself
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Chapters
1. We Put the Inner Child to Bed—And It’s Time for Recess (00:00:00)
2. The Case for Play in Midlife (00:00:07)
3. Meet the Coaches & Mission (00:00:56)
4. Why Life Feels Flat (00:02:12)
5. Awe, Positive Psychology, and Learning (00:04:11)
6. Flexibility Versus Rigidity (00:06:36)
7. Faith, Saging, and Growth Mindset (00:11:19)
8. Fearlessness and Safe Exhilaration (00:16:15)
9. Comfort Zones, Ruts, and Risk (00:19:19)
10. Gendered Traps: Outcomes vs Experience (00:21:06)
11. The Wonder List and Reframing Self (00:23:18)
12. Six-Step Practical Review (00:25:13)
13. Reviving Playfulness in Relationships (00:27:18)
14. Takeaways, Play Personalities, Play Dates (00:29:39)
15. Coaching Contacts & Next Steps (00:31:36)
16. Closing Rally: Your Wonder Is Waiting (00:33:47)
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