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Chip Conley · Lifestyle

The Midlife Chrysalis

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

Episodes

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Surfing at 87, Writing at 91: James Flaherty’s Rules for Life

14 Sep 2026
48m
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Redefining midlife as a transformative "chrysalis" rather than a crisis, this conversation with 91-year-old Jim Flaherty highlights the pursuit of a meaningful, purposeful life. Flaherty, a former advertising creative director and innkeeper, emphasizes that aging is not about maintaining youth but remaining useful. He ...

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From Role to Soul: Who Are You Without What You Do? | Connie Zweig

11 Sep 2026
49m
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Aging is a continuous process of growth that requires a fundamental shift from external "doing" to internal "being." As individuals transition into later life, the ego—often defined by professional roles and productivity—must recede to allow the soul to lead. This transformation necessitates "shadow work," the process ...

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You Can’t Rush Grief: Learning to Feel What We’ve Lost

09 Sep 2026
22m
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Grief functions as a natural indicator of what one truly values, serving as an inevitable consequence of deep love. Rather than a linear process, it arrives in unpredictable waves that require patience rather than forced acceleration or spiritual bypassing. The sudden loss of a beloved pet, Jamie, highlights the intens...

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What Happens After You Achieve Your Biggest Dream? | Paul Harris

07 Sep 2026
43m
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Professional athletes often face significant identity crises upon retirement, transitioning from high-profile careers to a sense of anonymity. Paul Harris, a former South African international cricketer, highlights the common struggle of losing one's primary identity, noting that many retired athletes experience depres...

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From Doing to Being: The Power of Presence | Teddi Dean

04 Sep 2026
49m
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Mindfulness extends beyond formal meditation to encompass any practice that fosters presence, awareness, and a deeper connection to one’s body and breath. Teddi Dean, a former professional skateboarder and filmmaker turned mindfulness teacher, shares his journey from a high-intensity lifestyle to finding sobriety and p...

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Curiosity Is the Secret to a Richer Life

02 Sep 2026
24m
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A psychologically rich life functions as a vital third pillar of well-being, complementing traditional pursuits of happiness and meaning. Unlike the pursuit of feeling good or doing good, this state prioritizes curiosity, diverse experiences, and a growth mindset. Engaging in novel challenges—such as learning a new ski...

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We’re Living Longer. Why Isn’t Society Ready? | David Sinclair

31 Aug 2026
45m
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Societies are currently aging at an unprecedented rate, yet governments remain largely unprepared, with pension, health, and social care systems struggling to keep pace. David Sinclair, head of the International Longevity Centre, argues that the focus must shift from radical life extension to immediate policy reform. K...

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From Achievement to Fulfillment: Building Your Life 3.0 | Seth Streeter

28 Aug 2026
47m
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Could Living Together Be the Secret to Aging Better?

26 Aug 2026
23m
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You Got Everything You Wanted. Now What? | Edward Sullivan

24 Aug 2026
50m
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Follow the Energy, Not the Career Script | Arun Gupta

21 Aug 2026
49m
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Midlife serves as a transformative chrysalis rather than a crisis, offering a unique opportunity to integrate purpose into professional life. Arun Gupta, venture capitalist and CEO of NobleReach, challenges the traditional "learn, earn, return" career trajectory, advocating instead for weaving these phases together thr...

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How to Discover the Gift That’s Uniquely Yours?

19 Aug 2026
15m
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Excavating one’s essence serves as a powerful tool for both professional differentiation and personal alignment during midlife. By repeatedly asking "What business are we in?" or "What gift can I offer?", individuals and organizations can move beyond superficial categories to uncover their unique value proposition. Thi...

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How to Talk to People You Profoundly Disagree With | Shamil Idriss

17 Aug 2026
45m
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Why Retirement Is the Wrong Goal | Ken Dychtwald

14 Aug 2026
47m
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Midlife represents a profound period of transformation—a "chrysalis"—rather than a crisis or the beginning of the end. Ken Dychtwald, a pioneer in the study of aging and founder of AgeWave, argues that increased longevity has fundamentally shifted the human life course, necessitating new social infrastructure for the e...

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Why Midlife Feels Stuck (And How to Break Free)

12 Aug 2026
23m
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Reframing, or cognitive reappraisal, serves as a vital psychological tool for overcoming midlife "stuckness" and navigating involuntary transitions. Rather than optimizing for past success, midlife requires shifting the aperture to embrace new perspectives and possibilities. This process involves moving from rigid rout...

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How Psilocybin Can Change Your Life After 40 | Neil Markey

10 Aug 2026
55m
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Your Brain Is Lying to You About Happiness | Dr. Laurie Santos

07 Aug 2026
45m
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Happiness often eludes individuals because the mind misidentifies the sources of fulfillment, prioritizing material gains or professional accolades over purpose and connection. Dr. Laurie Santos, a renowned happiness professor at Yale, argues that humans frequently fall into irrational patterns—similar to those observe...

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Why High Achievers Still Feel Like Imposters

05 Aug 2026
25m
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Imposter syndrome often stems from a fear of being exposed as unqualified, but shifting toward an "explorer syndrome" allows individuals to embrace the journey of learning and growth. Personifying the inner critic with humorous labels helps detach from self-criticism and performance anxiety. Distinguishing between high...

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The Biggest Lies We've Been Told About Aging | Ashton Applewhite

03 Aug 2026
46m
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Ageism stems from the false, monolithic perception of older people as a "sad gray mass," when in reality, the defining characteristic of later life is heterogeneity. Aging is a lifelong process rather than a decline, and societal biases—often driven by "chrononormativity"—impose rigid, arbitrary timelines on life miles...

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Why Your 70s Can Be Your Most Meaningful Years | Dr. Philip Pizzo

31 Jul 2026
49m
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Midlife represents a period of profound transformation rather than a crisis, serving as a chrysalis for the most meaningful chapters of life. Dr. Philip Pizzo, former Dean of Stanford Medical School, demonstrates this by transitioning from a distinguished career in medicine and science to spiritual care and rabbinical ...

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