The Midlife Chrysalis

What if you gave yourself 30 days… with nothing planned?

In this episode, Chip Conley shares a deeply personal idea he’s exploring: stepping away from a busy life for a full month: no schedule, no expectations, just space to listen, reflect, and reset.

It’s not about escaping life. It’s about returning to it with more clarity and intention.

Few ideas from the episode that might stay with you:

• What it actually means to “...

In this powerful episode of the Midlife Chrysalis, Chip Conley sits down with two women who’ve pushed their limits, physically, emotionally, and psychologically, and came out transformed.

Meet Rebecca Rusch, a world-class endurance athlete who biked the Ho Chi Minh Trail to reconnect with her late father, and Jaimie Lusk, a former Marine turned psychologist helping veterans heal from deep psychological wounds. Together, they reveal...

Most people don’t realize they’re living someone else’s life until it’s too late.

In this episode, Chip Conley sits down with Bonnie Wan, a renowned brand strategist and author of The Life Brief, who has spent decades studying human behavior, and now helps people redesign their lives with clarity and intention.

Through her “Life Brief” method, people learn how to cut through the noise and make decisions that truly align with ...

You don’t stay relevant by knowing more. You stay relevant by staying curious.

In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to break down why curiosity, not experience or intelligence, is the real edge in midlife and beyond.

Here’s what stands out:

• Curiosity is the antidote to irrelevance
• Asking better questions beats having the right answers
• Midlife requires a shift from knowledge to wisdom
• Learning for ...

Midlife might be the moment everything finally starts to make sense.

In this episode of The Midlife Chrysalis, Chip sits down with branding expert Robin Fisher Roffer, who spent over 30 years shaping major brands, to explore how those same principles can help you reinvent your life.

Robin shares her own powerful transition, stepping away from a successful career to start a whole new chapter, and what she’s learned along the w...

Midlife can feel confusing, off track, or quietly unsettled, and you’re not the only one feeling it. 

In this episode of Midlife Chrysalis, Lee Johnson, a mindfulness guide and teacher, shares his journey from ranch life to guiding others through mindfulness and “inner tracking,” offering a grounded and deeply human perspective on finding your way without a clear plan. 

Here’s what you’ll take away:

• Why feeling lost in midli...

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...