The Midlife Chrysalis

After everything you’ve been through, keeping your heart open can feel like a lot to ask. But there’s still room for connection, beauty, and a life that feels more like you.

Author and Omega Institute cofounder Elizabeth Lesser joins Chip Conley to explore how divorce, loss, and aging can deepen our lives without hardening our hearts. Drawing on her books Broken Open and the forthcoming Stay Open, she shares insights on how to:

“Stay positive” can feel hollow when cancer returns, someone you love dies, and your marriage is ending.

In this Wisdom Wednesday episode, MEA founder and author Chip Conley joins Derek Gehl for a deeply personal conversation about facing all three. Drawing on his upcoming book, The Art of the Reframe, Chip shares how he’s finding a way forward without pretending the pain isn’t real.

You’ll discover how to:

You can build a successful life and still reach a point where you need to rebuild yourself.

In this episode, Chip Conley sits down with David Gottfried, co-founder of the U.S. Green Building Council and pioneer of the green building movement, for a candid conversation about success, loss, and reinvention.

David shares how transforming an industry was followed by a deeply personal transformation when his 20-year marriage ended and forced him to rethink who he was.

They explore:

Your first love can stay with you for decades. So can the story you keep telling yourself about it.

Actor and filmmaker Juan Pablo Di Pace joins Chip Conley for a personal conversation about love, memory, and the past’s hold on our present. Through his film Before We Forget, he revisits a formative teenage love and explores how a memory can be both something we treasure and a wound we carry.

He shares:

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?

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:

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:

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 quietly put aside.

You’ll hear:

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:

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 this...

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.

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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 alive.

Key insights include:

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:

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 and leadership, and what it really takes to build...

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:

What if the thing that makes you different has been there all along, you just haven’t named it yet?

In this Wisdom Wednesday, Chip Conley and Derek Gehl explore how to “excavate your essence” and uncover the unique gift that can guide your work, choices, and life.

You’ll discover:

How do you find common ground with someone you profoundly disagree with?

At a time when political, religious, and cultural divisions seem deeper than ever, peacebuilder Shamil Idriss, CEO of Search for Common Ground, shares what decades of bringing people together have taught him about trust, conflict, and human connection.

In this conversation with Chip Conley, Shamil explores:

Midlife isn't the beginning of the end. For more than 50 years, Dr. Ken Dychtwald, psychologist, bestselling author, and founder of Age Wave, has studied what it really means to grow older.

In this conversation, he explains why midlife isn't the beginning of the end, but the start of one of life's most meaningful transformations.

In this episode, you'll discover:

Don't wait until it's too late to tell someone what they mean to you.

In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it?

In this episode, you'll learn:

Could one guided psychedelic experience transform the way you think, feel, and live?

In this episode of The Midlife Chrysalis, Chip Conley speaks with Neil Markey, CEO of Beckley Retreats, former Army Ranger captain, McKinsey consultant, and Harvard public health student, about the growing role of psilocybin in personal transformation and mental well-being.

Together, they explore:

We've been chasing happiness the wrong way. Dr. Laurie Santos explains what actually works.

Join Chip Conley and Dr. Laurie Santos, Yale's renowned happiness professor and creator of the university's most popular course, for a thought-provoking conversation on the science of happiness, the opportunities of midlife, and the habits that lead to a more fulfilling life.

In this episode, you'll discover:

Do you ever feel like you're not good enough, even when you're succeeding?

You're not alone. In this Wisdom Wednesday, Chip Conley explores why imposter syndrome follows so many high achievers and, more importantly, how to break free from it.

In this conversation, you'll discover:

In this eye opening conversation, bestselling author and aging activist Ashton Applewhite challenges everything we think we know about growing older. She reveals why many of our fears about aging come from culture, not reality, and explains how getting older can bring more freedom, confidence, and purpose.

In this episode, you'll learn:

What if your most meaningful chapter begins after 70?

Most people think aging is about slowing down. Dr. Philip Pizzo believes it's about discovering new purpose.

In this inspiring conversation, Chip Conley sits down with Dr. Philip Pizzo, former Dean of Stanford Medicine, founder of the Stanford Distinguished Careers Institute (DCI), physician, educator, and now a spiritual care provider, to explore how we can navigate life's biggest transitions with meaning.

In this episode, you'll discover:

Don't wait until it's too late to tell someone what they mean to you.

In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it?

In this episode, you'll learn:

At an age when many people are slowing down, Pat Whitty walked 200 miles on Spain's Camino de Santiago — alone. But what started as a physical challenge became a profound journey of self-discovery, purpose, and spiritual renewal.

In this inspiring conversation, Chip Conley sits down with Pat to explore what happened when he stepped away from the noise of everyday life and spent 16 days walking with nothing but his thoughts.

In this episode, you'll discover:

Play isn't just for kids. It's one of the most powerful tools for navigating change, finding purpose, and becoming more fully yourself.

In this episode of Midlife Chrysalis, Chip Conley sits down with Kristine Michie founder of the Playful Podcast, and JD Schramm, communication expert and former Stanford professor, to explore how play, storytelling, and authenticity can transform the way we approach midlife.

What you'll discover: