The Midlife Chrysalis

AI can save you hours. But are you handing over more than your workload? In this Wisdom Wednesday episode of the Midlife Chrysalis podcast, Chip Conley and Derek Gehl explore how to use AI without losing your voice, creativity, or judgment. Together, they discuss: How they use AI to save time on research and everyday work Why polished writing can lose the personality that makes it yours How outsou...

That book you’ve been meaning to write isn’t going to write itself. And according to publishing expert Kelly Notaras, you don’t need a perfect plan, a polished first chapter, or even a publisher to get started. Kelly, founder of KN Literary Arts and author of The Book You Were Born to Write, has helped nearly 3,000 authors bring their ideas to the page. In this conversation, she shares what decade...

You can spend years chasing happiness and miss the life happening right in front of you. In this episode of The Midlife Chrysalis, Chip Conley joins mindfulness teachers Mark Coleman and Lori Schwanbeck to explore how to feel more present, connected, and fully alive in midlife. Together, they explore: How changing what you pay attention to can change your experience of life Why nature makes mindfu...

The kids have moved out. Family gatherings feel complicated. Suddenly, the holidays you used to love leave you wondering where you belong. In this Wisdom Wednesday episode, MEA founder Chip Conley joins host Derek Gehl to explore why holidays change in midlife and how new traditions can bring back a sense of connection. Discover how to: Build celebrations around people you genuinely want to spend...

The hardest conversations are often the ones that help us grow. John Baird has spent 30 years coaching leaders at Apple. At 82, he’s still coaching, trying new things, and making time for what matters most. In this episode of The Midlife Chrysalis, John joins Chip Conley for a warm, candid conversation about leading with heart, making tough decisions, and building a meaningful life. He shares: How...

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,...

“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 discov...

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 wh...

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 sh...

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...

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 ab...

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 ma...

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 disco...

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...

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 a...

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 h...

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 H...

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 e...

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 inv...

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 opportuniti...

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 s...

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 meaningfu...

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...

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...

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...