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PODCAST

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

education self-improvement

All Episodes

00:44:47

He Died 11 Years Ago. Their Relationship Never Ended....

The Midlife Chrysalis ·

2026/10/05

Eleven years after losing her husband, the pain has changed. The love hasn’t.Dr. Lucy Kalanithi, physician and widow of Paul Kalanithi, author of When Breath Becomes Air, joins Chip Conley for a deeply personal conversation about grief, caregiving, uncertainty, and building a meaningful life after profound loss.Drawing on her experience as a wife, mother, caregiver, and doctor, Lucy shares what more than a decade of living with grief has taught her:Why death doesn’t necessarily end our relationship

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00:35:13

Why Life Can Get Harder and Happier After 50 |...

The Midlife Chrysalis ·

2026/10/02

Jonathan Rauch had reached the top of his career, yet each year he felt less satisfied. Then came the loss of his parents, his job, and a startup he had tried to build. To his surprise, his sense of contentment began to grow.Rauch is a journalist and the author of The Happiness Curve, The Constitution of Knowledge, and Cross Purposes. He joins Chip Conley to explore what his personal experience and research reveal about getting older, and why the future looks more troubling for younger adults.In

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00:27:31

The Hardest Leadership Lesson: Let Someone Else Be...

The Midlife Chrysalis ·

2026/09/30

Being the person who saves the day feels good. But letting someone else do it can make you a better leader.MEA founder Chip Conley joins Derek Gehl to talk about one of the hardest changes in his career: moving from hero to coach. Chip shares how he is learning to step back, trust his team, and make room for others to lead.Why having all the answers can hold your team backHow asking questions helps others grow into leadersWhy purpose matters as an organization gets biggerHow to build something that

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00:35:32

What Changes When You Finally Let Go of Control? |...

The Midlife Chrysalis ·

2026/09/28

Success can look impressive on a résumé and still leave you wondering who you really are.At 76, Harvard Business School professor and former Morgan Stanley executive Thomas DeLong is rethinking some of the biggest lessons he has learned about leadership, courage, relationships, and success. In this conversation with Chip Conley, he reflects on:Why letting go of control can deepen relationshipsHow to move from image management to essenceWhy vulnerability is a powerful form of courageHow inherited

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00:51:39

Let Life Lead: A Different Way to Navigate Midlife |...

The Midlife Chrysalis ·

2026/09/25

Sometimes the most powerful way forward begins by doing less.Filmmaker Nic Askew has spent more than two decades capturing what happens when people stop performing and simply allow themselves to be seen. Through his Soul Biographies, he has discovered a different way of approaching connection, identity, and life itself.In this episode, Nic explores:Why “starting with nothing” can reveal what effort cannotHow stillness creates space for the soul rather than the ego to leadWhy doing less can help us

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00:24:16

Be Useful, Not Youthful: The Secret to Aging Well

The Midlife Chrysalis ·

2026/09/23

At some point in midlife, achievement stops being enough. The titles matter less, the phone may stop ringing, and the question becomes: where does your value come from now?In this episode of Wisdom Wednesday, MEA founder Chip Conley joins Derek Gehl to explore the shift from achievement and admiration toward generativity, usefulness, and helping others grow.Key insights include:Why feeling invisible doesn’t mean becoming irrelevantHow to move from “sage on the stage” to “guide on the side”Why being

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00:56:35

Can Your Beliefs Actually Change How You Age? | Shawn...

The Midlife Chrysalis ·

2026/09/21

We’re taught to expect decline as we get older. But the science tells a far more hopeful story.In this episode, bestselling author and positive psychology expert Shawn Achor joins us to explore how our beliefs can shape the way we age. Drawing from his new book, The Power of Beliefs, groundbreaking research, and his own midlife experience, Shawn reveals why getting older can bring new opportunities for growth, meaning, happiness, and wisdom.You’ll discover:How beliefs about aging can influence our

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00:50:34

He Spent 10 Years Filming the World’s Oldest People |...

The Midlife Chrysalis ·

2026/09/18

What can the world’s oldest people teach us about time, aging, and being alive?Academy Award nominated filmmaker Sam Green spent 10 years filming people who held the title of the world’s oldest living person. His documentary The Oldest Person in the World began as a curiosity but became a deeply personal exploration of mortality, connection, and how we use the time we have.In this episode, Sam shares:What life really looks like at 115 and what seems to matter mostThe surprising traits he noticed

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00:22:19

Why Birthdays Matter More as We Get Older

The Midlife Chrysalis ·

2026/09/16

Why do we celebrate birthdays as kids, then slowly stop celebrating ourselves as we get older?In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl for a conversation about birthdays, aging, and why life’s milestones deserve more attention, not less.After decades of marking his own milestone birthdays in memorable ways, Chip shares why celebration has become even more meaningful as he’s grown older and faced his own mortality.Key insights from the episode:Birthdays are more than a

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00:48:49

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

The Midlife Chrysalis ·

2026/09/14

At 91, James Flaherty isn’t slowing down. He’s still writing, creating, learning, and planning what comes next.A former advertising executive, entrepreneur, innkeeper, and author who wrote five books in his 80s, James joins Chip Conley to share what nine decades of living have taught him about aging well and staying fully engaged with life.In this episode, James shares:Stay useful, not youthful. Growing older brings experience and wisdom that can be put to work for others.Always have a reason to

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00:49:44

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

The Midlife Chrysalis ·

2026/09/11

Aging isn’t just about getting older. It’s about discovering who you are when the roles that once defined you begin to fall away.In this episode, Chip Conley sits down with Connie Zweig, author of The Inner Work of Age, to explore the deeper psychological and spiritual work of midlife and beyond.Connie shares what it takes to move from simply growing old to becoming an elder, including:Moving from role to soul: Why identity built around achievement and productivity may need to loosen as we

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00:22:56

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

The Midlife Chrysalis ·

2026/09/09

Some losses hit harder than we ever expect, and grief doesn’t follow our timeline.In this deeply personal episode of Midlife Chrysalis, Chip Conley opens up about the unexpected death of his beloved dog Jamie and what the experience has taught him about grief, love, and loss.Key insights from the episode:Grief comes in waves. It can surface as sadness, anger, exhaustion, or simply the need for space.You can’t rush grief. Searching for meaning too quickly can keep us from actually feeling what we’ve

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00:43:26

What Happens After You Achieve Your Biggest Dream? |...

The Midlife Chrysalis ·

2026/09/07

What happens when the identity you've spent your entire life building suddenly disappears?Former South African international cricketer Paul Harris reached the highest level of his sport, but retiring at just 33 forced him into an even bigger challenge: discovering who he was beyond cricket. In this powerful conversation, Paul shares the emotional reality of life after professional sports and the lessons that helped him build a meaningful second chapter.In this episode, you'll learn:Why major

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00:49:58

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

The Midlife Chrysalis ·

2026/09/04

Sometimes the most powerful thing we can do is stop doing and simply be present.In this episode, Chip Conley talks with Teddi Dean, former Bones Brigade skateboarder turned filmmaker, mindfulness teacher, and Head of Mind & Body at MEA. Teddy shares his journey through sobriety, yoga, meditation, and decades of exploring what it means to live with greater awareness.You’ll discover:Why stillness can be transformative and help us reconnect with ourselves.How 10 to 20 minutes of daily mindfulness

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00:24:24

Curiosity Is the Secret to a Richer Life

The Midlife Chrysalis ·

2026/09/02

Happiness and purpose may not be enough for a truly rich life.In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore psychological richness and why curiosity, new experiences, challenge, and spontaneity become especially valuable as we age.You’ll discover:Why psychological richness matters as we get older and how curiosity keeps us engaged with life.The question that can reshape your next decade: What will you regret not learning, doing, or investing in 10 years from

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00:45:23

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

The Midlife Chrysalis ·

2026/08/31

The longevity revolution isn’t coming. We’re already living it, and we’re not ready.In this episode, David Sinclair of the International Longevity Centre joins Chip Conley to explore what longer lives mean for all of us and why society needs to catch up with a future that’s already here.In this conversation:Why the real longevity challenge isn’t living to 100, but adapting to longer lives todayWhy prevention needs to play a much bigger role in how we approach health and agingHow longer lives are

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00:47:32

From Achievement to Fulfillment: Building Your Life...

The Midlife Chrysalis ·

2026/08/28

Success can look impressive on the outside and still leave you feeling like something is missing.Seth Streeter, co-founder of Mission Wealth, spent decades building a successful career while constantly pushing himself to achieve more. But after personal crisis, health struggles, and a major identity shift, he began questioning what success was really for.In this episode, Seth shares his journey from achievement to Life 3.0, a new chapter centered on fulfillment, purpose, and what truly makes us come

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00:23:37

Could Living Together Be the Secret to Aging Better?

The Midlife Chrysalis ·

2026/08/26

Growing older is changing. Maybe the way we live should change with it.In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to explore a new approach to later life: shared homes that combine independence, connection, and community.Drawing on MEA’s growing Golden Girls experiment, Chip shares:Why traditional senior living and aging in place don’t work for everyoneWhat MEA has learned from its first shared homes and Golden Girls retreatsWhy privacy, flexibility, and compromise are

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00:50:19

You Got Everything You Wanted. Now What? | Edward...

The Midlife Chrysalis ·

2026/08/24

What happens when you achieve the success you've worked for... and it still doesn't feel like enough?In this episode of The Midlife Chrysalis, Chip Conley sits down with executive coach and Velocity Coaching founder Edward Sullivan to explore one of the most overlooked challenges of midlife: figuring out what comes after success.Drawing on years of coaching founders, CEOs, and high achievers, Edward shares why so many people feel restless after reaching major goals, how AI is reshaping work

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00:49:48

Follow the Energy, Not the Career Script | Arun Gupta

The Midlife Chrysalis ·

2026/08/21

Your job title tells people what you do. The problem you care about tells them who you are.Arun Gupta, CEO of NobleReach and co-author of The Mission Generation, joins Chip Conley for a thoughtful conversation about finding purpose, staying curious, and creating a meaningful career at every stage of life.Some of the ideas they explore:Why following your energy can lead you somewhere a career plan never couldHow becoming a beginner again can bring fresh energy to midlifeWhy learning, earning, and

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