The Midlife Chrysalis

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 with intention.

Pam shares:

• ...

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 feels like a breakdown, why i...

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, they reflect on:

• How Gavin’s upbringin...

What happens when success stops working and midlife hits hard?

Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapter. After building a global brand and achieving massive success, Blake found himself facing a deep midlife reckoning marked by depression, loss of identity, and an urgent search for meaning beyond achievement.

Blake opens up about:

- How selling part of TOMS triggered an unex...

What if aging alone isn’t the only option?

As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose community instead of solitude?

In this Wisdom Wednesday episode, Chip Conley, founder of Modern Elder Academy, joins Derek Gehl to explore the early-stage idea behind Golden Girls–style living, an intentional housing experiment he’s beginning in Santa Fe to address loneliness, gray ...

Aging in America has never been the same for everyone. Chip Conley sits down with Ray Jetson, pastor, former Louisiana legislator, and author of Aging While Black, to explore why aging isn’t a race-neutral experience and what it really means to age well in a system that was never built for everyone.Ray shares a simple, powerful way to rethink aging through community, innovation, and shared wisdom across generations.

In this epis...

Most leaders are chasing short-term wins and missing the long game.

In this episode, Chip Conley talks with Rand Stagen, founder of the Stagen Leadership Academy, about what’s quietly breaking leadership today and how to lead with purpose, perspective, and staying power.

Rand shares hard-earned insights from decades of working with CEOs and entrepreneurs who want more than success, they want meaning.

You’ll learn:

- Why sho...

Most companies are racing toward AI, efficiency, and scale while quietly losing the one advantage that actually sustains great leadership: wisdom.

In this Wisdom Wednesday episode, we reveal why culture, lived experience, and human judgment matter more than ever. Chip draws on decades of leadership experience to explain why many organizations are losing their edge and what they can do to reclaim it.

In this episode, you’ll ...

Have you ever reached a point in life where what once worked… suddenly doesn’t?

In this warm conversation with Chip, Ben Katt, MEA’s faculty in residence and author of The Way Home, offers a hopeful reframe of midlife. Rather than seeing it as a breakdown, Ben invites us to see this season as a meaningful transition, one that asks us to let go of old roles and reconnect with who we truly are.

In this episode, you’ll discover:

- W...

What if the wellness advice you followed for years stops working after 50?

In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, and Schuyler Grant, founder of Kula Yoga Project, share how their approach to health quietly but radically shifted in midlife, and why many popular wellness habits fall short as we age.

With decades spent in yoga, wellness festivals, and lived experience, they share what actually...

Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickly and share a simple, practical framework for building habits that last. Drawing from real-life experience, we break down how to turn good intentions into daily actions, without relying on motivation alone.

In this episode, you’ll learn:

- Why most resolutions fail

- How habit stac...

Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to evolve, leaving many people feeling stuck in between what was and what’s next.

In this episode, Kari Cardinale, Chief Content Officer and partner at Modern Elder Academy, explains why these moments aren’t breakdowns but transitions, and why learning to navigate them is an essential l...

He didn’t plan on being successful. He just followed what pulled at him and kept letting go when it stopped working. In this episode, Stacy Peralta, legendary skateboarder, filmmaker behind Dogtown and Z-Boys, and modern elder, shares how a life built on passion, curiosity, and vulnerability led him from skateboarding to filmmaking to painting, without clinging to any single identity.

Rather than chasing security or certainty, ...

In this Wisdom Wednesday episode, Chip Conley, entrepreneur, author, and founder of MEA, opens up about the quiet disappointment many high achievers feel after they’ve “made it.”

Through stories from building iconic companies, guiding Airbnb’s founders, and navigating midlife reckoning, Chip explores the success treadmill, and why chasing the next win so often leaves us unsatisfied.

In this conversation, you’ll learn:

- Why s...

What if the real risk in midlife isn’t change but staying comfortable?

In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Margie Warrell, global expert on courage and bestselling author of The Courage Gap, to explore why so many smart, capable people feel stuck and how to move forward with clarity and bravery.

Drawing from her journey from a rural Australian farm to the world stage, Margie shares powerful i...

Dating in midlife can feel strangely hard, even when you’ve done the work, built a full life, and know yourself better than ever. If you’ve ever thought, “Why is this still so complicated?” this episode is for you.

In this conversation, I sit down with Rachel Greenwald, Harvard MBA and veteran matchmaker who has helped guide nearly 1,000 marriages. With warmth, humor, and deep insight, Rachel reframes dating not as luck but as a le...

Feeling stuck in midlife? You might be in your chrysalis, not a crisis.

In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation.

Chip shares:

• The three stages of every transition and where most people get stuck

• What really happens inside the messy middle

• Why men and women experience midlife so differently

• H...

What if midlife became your chance to ROAR, not retire?

In this powerful conversation, bestselling author and longevity visionary Michael Clinton shares why your 40s, 50s, and beyond are actually the most exciting and opportunity-filled decades of your life. From his rise to the top of Hearst Magazines to running marathons on seven continents and earning a new degree at 67, Michael reveals how reinvention is not only possible, i...

Ever wondered why some people get stronger, wiser, and more grounded with age?

In this powerful conversation, Laird Hamilton and Gabby Reece reveal why midlife is actually the most dynamic, resilient, and liberating season of life. They open up about growing up on islands, how they met, what keeps their partnership strong, and why presence, patience, and community matter more than ever. From breathwork and injury recovery to ide...