The Midlife Chrysalis

Rich Roll on Reinventing Yourself After Rock Bottom


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What if hitting rock bottom was the best thing that ever happened to you?


In this raw and inspiring conversation, Rich Roll, a former addict turned world-class endurance athlete, shares how he rebuilt his life from scratch, facing failure, financial ruin, and identity loss to find real purpose.


With brutal honesty, he opens up about his addiction, fatherhood, marriage, legacy, and the heavy cost of chasing approval. If you're feeling stuck, burned out, or unsure what comes next, this conversation just might change how you see your own story.


Timestamps:

00:00 Introduction

01:13 Spine Surgery and Recovery

03:02 Losing Identity and Facing Stillness

05:47 Interviewing Master Interviewers

07:17 Life Begins at 40 & Rejecting the Race

11:06 How to Know You’re on the Right Track

13:42 Performance vs. Presence

15:25 Addiction, Achievement, and the Roots of Disconnection

19:49 The Midlife Chrysalis at Age 39

24:29 The Support of His Wife Julie

26:04 Lessons from Rich’s Midlife Chrysalis

32:14 From Blog to Writing a Book

38:10 Launching the Podcast & Relocating to Hawaii

42:27 Gaining Momentum

43:50 Financial Struggles and Family Impact

48:14 What Makes Rich Roll’s Podcast Different

51:58 The Importance of Genuine Curiosity

54:25 The Power of Vulnerability in Conversation

56:31 Rethinking Success and Slowing Down

01:01:46 Legacy, Family, and Showing Up


Learn more about MEA at ⁠https://www.meawisdom.com/


#MidlifeTransformation #RichRoll #SpineSurgeryRecovery #SobrietyJourney #PurposeInMidlife #EnduranceAthlete #AddictionRecovery #MidlifeReinvention #PersonalGrowth #PodcastLife #EmotionalResilience #LifeAfter40 #LegacyWork #AuthenticLiving #ModernElder

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The Midlife ChrysalisBy Chip Conley

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