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
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...
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 today
- Why ...
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 c...
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 everyone
- What MEA has learned from its first share...
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 r...
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 could
- How becoming a begin...
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 Airbnb uncovered “Belong Anywhere” by looking beyond what the company does to why it matters
- A simple five-questi...
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:
- Why being heard and respected matters more than bein...
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:
- Why midlife is a time of growth, not decline
- The powerful idea of "mi...
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:
- Why we struggle to expr...
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:
- Why midlife may be the ideal time for a psychedeli...
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:
- Why your brain often pushes you...
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:
- Why imposter syndrome doesn't disappear with success
- How to replace fear with curiosity and become an "explorer" instead of an imposter
- Why vulnerability ...
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