The Midlife Chrysalis

Watch a great film, then share dinner with the person who made it. That’s the spirit of the MEA Film Fest, where stories on screen spark conversations and connections in real life.

In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to preview the festival and explore a question at its heart: how can movies help us see midlife, aging, and our own possibilities differently?

• Get a preview of the films, special gues...

After decades at the top, John Donahoe found himself starting over at 65.

John has led eBay, ServiceNow, and Nike. But some of his most important lessons came from burnout, failure, and the difficult transitions between success and what comes next.

In this deeply personal conversation, John shares:

• Why stepping away at 55 changed the way he saw success and himself
• What 50 wise elders taught him about vitality, purpose, and aging
• How...

Midlife can feel like the life you built suddenly stops fitting. Caroline Myss believes there’s a deeper reason: this is when the soul begins asking something different of you.

In this powerful conversation, bestselling author and spiritual teacher Caroline Myss joins Chip Conley to explore the deeper meaning of midlife, purpose, identity, and surrender.

Caroline shares:

• Why a crisis of purpose may actually be a crisis of th...

You’ve built a life that looks successful. Yet the things you worked so hard for may no longer be what you want next.

In this Wisdom Wednesday episode, MEA founder Chip Conley joins Derek Gehl to explore finding purpose when familiar roles no longer feel fulfilling. From a corporate lawyer investing in her community to former business owners pursuing screenwriting, Chip shares how people are discovering possibilities they had ...

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 wi...

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 old...

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 back
• How asking questions helps others grow into leaders
• Why p...

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 relationships
• How to move from image management t...

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 cannot
• How stillne...

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 ...

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, happin...

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 reall...

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 ...

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...

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 ...

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&rsquo...

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 mean...

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 a...

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...