The Midlife Chrysalis

Most of us try to solve midlife. What if that’s exactly the wrong approach? In this episode, Chip Conley sits down with Bill Burnett and Dave Evans , the minds behind Designing Your Life, to rethink one of the most misunderstood seasons of adulthood. Drawing from design thinking, human curiosity, and decades of real-world experimentation, they offer a refreshing alternative to the pressure of “fig...

Real growth rarely happens when life feels comfortable. It begins when we slow down, question our patterns, and face the deeper truths about how we live and lead. In this episode of Midlife Chrysalis, Chip Conley talks with Diana Chapman, leadership coach and co-author of The 15 Commitments of Conscious Leadership. Drawing from decades of coaching founders and CEOs, Diana shares practical wisdom o...

The drive that made you successful may not be meant to lead you forever. In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Derek Gehl explore the shift from ego to soul, the defining transition of the second half of life. Drawing from his personal journey, his role as a “modern elder” at Airbnb, and insights from Richard Rohr and Connie Zweig, Chip reflects on what happens...

What if the real key to longevity isn’t a biohack but a wake-up call? In this episode, Dr. Brad Jacobs, longevity expert, integrative medicine pioneer, and former UCSF professor, shares what truly helps us thrive in midlife. After losing his father to cancer at 27, Brad made it his life’s work to understand how we can live longer and better. In this episode, we explore: What actually extends your...

In this episode of Midlife Chrysalis, poet and philosopher David Whyte explores why midlife often feels like losing your way and why that experience may be exactly what opens the door to deeper meaning. Drawing on poetry, psychology, and Dante’s famous “dark wood,” David explains how moments of uncertainty can become powerful turning points in our lives. In this conversation, he shares: Why midlif...

Midlife isn’t about adding more. It’s about letting go. In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore The Great Midlife Edit, the courage to release what has quietly run its course. Drawing from his near-death experience and the sale of his company, Chip shares what it really means to “empty your cup” and create space for what’s next. In this co...

What happens when the world sees a champion… but you’re still figuring out who you are? In this episode of The Midlife Chrysalis, Olympic legend Greg Louganis opens up about the life behind the gold medals and the deeper journey beyond fame. From childhood wounds and public adoration to living with HIV and facing mortality at 28, Greg shares how his identity has evolved over decades. You’ll hear:...

Midlife can feel unsettling even when life looks successful on paper. This episode explores why that discomfort appears and how it can become a source of clarity rather than crisis.  Our guest is Kieran Setiya , MIT philosophy professor and author of Midlife: A Philosophical Guide . Drawing from philosophy and lived experience, he offers a calm, deeply human way of understanding regret, time, ambi...

What happens when time stops feeling endless and starts feeling real? In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer reshaped his relationship with time, purpose, and urgency in midlife. Joined by Derek Gehl, Chip reflects on cancer scans, mortality, and why remembering that life is finite can actually deepen meaning, not fear. Together they explore: Why memento mor...

In this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From imposter syndrome to the emotional aftermath of the IPO, Brian shares what midlife has taught him about ambition, belonging, and finally realizing he is enough. In this episode, you’ll hear:• Why success didn’t fix his loneliness• How leadership evolved fr...

Midlife isn’t a crisis. It’s an invitation to come alive again. In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen , a neuroscientist at Johns Hopkins, and Ivy Ross , Chief Design Officer at Google, for a warm, eye-opening conversation about why creativity is essential to being human, especially in midlife. Drawing from their book Your Brain on Art, they share how art, p...

Ever notice how some friendships don’t end, they just stop deepening? You still care about each other, but the conversations feel thinner than they used to. In midlife, that quiet shift is more common than we admit. In this Wisdom Wednesday episode, Chip Conley , founder of MEA, joins Derek Gehl for a warm, honest conversation about friendship in the second half of life: why it changes, why it mat...

Ever wonder what happens when “success” still feels empty? At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself and create Midlife Male, a movement helping men find purpose, strength, and authenticity in midlife. In this episode, we dive into what modern masculinity really means, why so many men struggle with...

Midlife rarely falls apart all at once. It slowly grows quieter, fewer close friendships, less community, more doing and less belonging. In this episode of Midlife Chrysalis, Jeff Hamaoui, MEA co-founder and community builder, reflects on how midlife invited him to redesign his life around friendship, connection, and community. In a warm, thoughtful conversation, Jeff shares: - Why friendship is a...

Most of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions. In this Wisdom Wednesday episode, Derek and Chip explore how mentorship evolves when experience meets curiosity. Drawing on stories from Airbnb, intergenerational leadership, and lessons from unlikely teachers, Chip shows why the best mentors are still learning. In this...

We’re surrounded by information but many of us still feel unsure about how to live well. This episode gently explores why midlife pulls us toward wisdom, not more answers. Chip Conley is joined by bestselling author Eric Weiner (The Geography of Bliss, Man Seeks God, The Socrates Express), a curious guide who’s spent years learning from philosophers, cultures, and lived experience. Together, they...

What if losing everything was the only way to truly find yourself? MIT lecturer and artist Aithan Shapira shares how the collapse of his art career became the catalyst for profound reinvention. He explains why midlife isn’t about decline but transformation , a time to practice letting go, reframe purpose, and reconnect with what matters most. If you’re in a season of change, this episode will help...

What if midlife isn’t the end of your career story but the smartest place to rewrite it? In this episode of Wisdom Wednesday, Chip Conley joins Derek Ghel to unpack what really happens when people feel stuck at midlife, and why career change after 50 doesn’t require starting over or burning everything down. Drawing on his journey from boutique hotels to Airbnb to founding the Modern Elder Academy,...

He had everything going for him, until his body shut him down on live TV. In this episode, Dan Harris sits down with Chip Conley for a warm, honest conversation about ambition, anxiety, and what really changes in midlife. Dan opens up about the panic attack that forced him to slow down, his years inside high-pressure newsrooms at ABC, and the quiet realization that productivity, without presence,...

Cancer doesn’t just affect your health. It changes how you see yourself and your life. In this warm and honest conversation, Chip Conley sits down with Caryn Lerman to explore the emotional side of cancer that often goes unspoken. Together, they talk about identity shifts, caregiving, and what it really means to move through the messy middle of midlife after a diagnosis.  In this episode, you’ll h...

What if the way you start your morning is quietly shaping how your whole day feels? Chip Conley sits down with Derek Gehl to explore why so many midlife routines start to feel empty and how turning them into simple, meaningful rituals can bring more calm, clarity, and purpose to everyday life. Together, Chip and Derek share: Why routines can feel mechanical, while rituals help us feel present and...

In this episode, Chip Conley sits down with Christine Sperber, co-founder of MEA and master experience designer, to explore how awe, ritual, and community can bring us back to life in midlife. Drawing from ski town culture, life in Baja, and years of building transformational experiences, Christine offers a hopeful reframe of aging as something to design, not fix. In this conversation, Chip and Ch...

Midlife isn’t the end of the story, it’s the chapter where something new wants to begin. In this episode of Midlife Chrysalis , Chip Conley sits down with Pam McLean , pioneering coach, co-founder of the Hudson Institute of Coaching, and a guiding voice on adult development and the “bonus years.” Together, they explore why midlife isn’t about stepping back, but about letting go and moving forward...

Midlife isn’t falling apart. It’s asking for your attention. In this episode of Midlife Chrysalis, Chip Conley dismantles the idea of the “midlife crisis” and replaces it with a far more hopeful and powerful framework: midlife as a chrysalis, a necessary transition into a second adulthood. Drawing from social science, psychology, and his own deeply personal story, Chip explains why midlife often f...

What happens when ambition slows down, and wisdom begins to lead? Chip Conley , founder of Modern Elder Academy and host of Midlife Chrysalis , sits down with California Governor Gavin Newsom for a rare, deeply personal conversation shaped by nearly 30 years of mentorship and friendship. This is not a political interview, it’s an honest exploration of midlife, identity, and becoming. Together, the...