The Midlife Chrysalis

You’re taking care of your parents. You’re supporting your kids. But who’s taking care of you?

In this Wisdom Wednesday episode, Derek Gehl sits down with Chip Conley to unpack the reality of the sandwich generation and why midlife can feel more overwhelming than ever. 

Chip shares key insights on:

• The real emotional cost of caregiving

• Why this stage of life feels heavier today

• How to build a support system that actually h...

What if the chaos in your life isn’t the problem… but the turning point?

In this episode, Amy Elizabeth Fox, leadership expert and co-founder of Mobius, explains why today’s pressure, uncertainty, and stress are actually pushing us to grow in a deeper way. Through her work with top executives and her own life story, she shows what it really takes to lead and stay grounded when everything feels unstable.

Here’s what you’ll learn:

• W...

She had the perfect life - career, family, success - and a secret she kept hidden for decades.

In this episode, Katherine Dudtschak, a former top banking executive, opens up about coming out at 50, telling 80,000 employees, and risking everything to finally live in alignment with who she truly is.It’s an honest, deeply human story about what happens when you spend years living the life you’re “supposed” to live, and what it take...

What if the biggest factor for a longer, happier life isn’t health, but friendship?

In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to explore why so many people, especially men, struggle with connection in midlife, and how to change that.

Here’s what you’ll learn:

• Why friendship is the #1 predictor of longevity
• The difference between real vs transactional relationships
• Why men often lack deep connection and h...

He was bleeding out… and didn’t even know he was dying.

In this powerful conversation, war journalist and bestselling author Sebastian Junger shares the moment he came face-to-face with death and what he discovered on the other side.

From a sudden internal hemorrhage to a near-death experience that challenged everything he believed, Junger takes us deep into the edge between life and death… and back again.

But this episode...

Anarchism isn’t chaos. It might be the key to better leadership.

In this thought-provoking episode, Chip speaks with Ari Weinzweig, co-founder of Zingerman’s, a company that grew from a $22,000 deli into an $80M family of businesses built on an unconventional idea: trust people, give them dignity, and rethink hierarchy.

Ari shares the surprising philosophy that shaped Zingerman’s culture and explains why many traditional lead...

Most people imagine a midlife crisis as sports cars, bad decisions, and dramatic life changes. But what if midlife is actually something much deeper and more meaningful?

In this episode of Midlife Chrysalis, Chip Conley explores what really happens during midlife and why men and women often experience it differently. Chip shares insights from years of research and thousands of midlife transitions, revealing the real challenges peopl...

Why do so many relationships lose intimacy over time, even when love is still there?

In this episode of Midlife Chrysalis, Chip Conley talks with renowned couples therapist Terry Real, creator of Relational Life Therapy and bestselling author of Fierce Intimacy and The New Rules of Marriage. For decades, Terry has helped couples understand why connection fades—and how to rebuild it.

In this conversation, he explains:

• Why love requ...

The moment that breaks your life can also be the moment that transforms it.

In this episode of Midlife Chrysalis, Chip Conley sits down with comedian and writer Pete Holmes for a deep and surprisingly funny conversation about heartbreak, spirituality, and the search for meaning. Pete shares how a painful divorce in his twenties pushed him to fully commit to comedy and set him on a journey into consciousness, psychedelics, fatherhoo...

What if the most powerful move you could make at midlife… is to pause?

In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more people over 50 are choosing a reset instead of racing toward retirement.

Chip challenges the old “learn, earn, retire” model and introduces a new idea: the midlife pit stop — a courageous break to refuel before the next chapter.

...

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 “figuring it all out.”

Instead of ...

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 on how awareness can transform re...

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 when achievement stops being en...

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 life (and what’s a distraction)
• Why ...

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 midlife can feel like exile from your ol...

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 conversation, you’ll learn:

• Why midli...

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:

• How early trauma shaped his ...

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, ambition, and meaning in the middle years ...

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 mori can bring clarity, not darkness
• ...