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What if we framed midlife not as a crisis but as a transformative chrysalis—a liminal period where profound awakenings unfold?

What if we saw it as an opportunity to shed old layers, unfurl our wings, and share the pollen of our wisdom with the world?

Guiding us from pupa to butterfly, we have the Monarch himself, @chipconley

Returning to the show for the second time (Chip first appeared on episode 681), Chip founded the Modern Elder Academy, the pioneering midlife wisdom school dedicated to transforming aging. 

Today’s conversation revolves around how we conceptualize and define life stages, the concept of Age Fluidity, the age curve of happiness, and the importance of cultivating regenerative communities.

We also explore Chip’s personal journey with cancer, the distinction between showing up and showing off, the role of being a conduit for ideas and collaboration, the essence of being a Modern Elder, the concept of age apartheid, and the value of generational dinners.

For individuals seeking to infuse greater purpose and satisfaction into their professional journey, especially those who have dedicated a significant portion of their career to a specific path and are now pondering fresh opportunities, this conversation is a must-listen.

Episode 806.

To watch or listen, hit the link in bio.

✌🏼🌱 - Rich

What an honor it was to do this segment on the TODAY show with Hoda & Jenna and humbling to receive their vibrant support.

Check out the midlife wisdom school I founded, @meawisdom to deepen and enrich your journey and connect with people on the same path.

What do you do when the version of yourself you built for decades no longer fits your life?

In this conversation, I sit down with therapist and former theater director Ben Yalom for a warm, honest discussion about reinvention, grief, aging, identity, and the courage it takes to change direction in midlife.
After spending years in experimental theater, Ben found himself at a crossroads during COVID. What followed was an unexpected transition into psychotherapy, where he now combines storytelling, movement, curiosity, and emotional exploration in deeply human ways.

It’s one of those conversations that stays with you long after it ends.

Listen now if you’re navigating change, rethinking your path, or wondering who you’re becoming next. Link is in my bio.

In this episode, I sit down with gerontologist Kerry Burnight, who has spent decades working with people in their 80s, 90s, and even 100s. And what she’s learned might completely change how you think about aging, and how you choose to live right now.

Kerry introduces a powerful idea called joyspan, the missing piece between how long you live and how well you live. And the truth is, most people are getting this wrong.

This is one of those conversations that makes you pause, reflect, and maybe rethink how you’re living your life. Watch now using the link in my bio!

Ringing the bell as I finish my radiation regime, at least for this round. Now just dealing with the side effects of hormone deprivation therapy.

The moment everything starts falling apart might be the moment your life finally comes together.

In this episode, I sit down with entrepreneur and author of Grow or Fold, Matt Ross, to explore a powerful story of midlife reinvention. From a high-pressure career in radio to building purpose-driven businesses, Matt shares how personal crisis, burnout, and uncertainty became the catalyst for real change.

If you’re at a crossroads, questioning what’s next, or just know there’s more out there for you—this conversation will hit home.

Watch now and take the first step toward your next chapter. Link is in my bio.

What if the life you built… no longer feels like yours?
In this powerful episode, Kelly Wendorf joins me for a raw conversation about loss, identity, and the moment everything shifts. From caring for a dying parent to rediscovering yourself through nature, this episode goes straight to the heart of what it means to truly live.

If you’re going through a big shift, dealing with loss, or just feeling like something’s off—this one will really hit.

👉 Watch the full episode now. Link in bio!

Back in San Francisco but there are no humans here

In this powerful conversation, Elizabeth White, author of 55, Underemployed, and Faking Normal, shares how losing everything during the recession led her to uncover a hidden crisis affecting millions of women over 50… and a bold new solution.

This episode reframes what it means to grow older and how to do it with more connection, security, and intention.

🎧 Listen now and rethink your future. Link in bio.

Chip Conley is on a midlife mission.

After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018 in Baja California, Mexico.

Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world’s first ‘midlife wisdom school’.

The academy opened a campus in 2024 on a 2,600-acre regenerative horse ranch in Santa Fe, New Mexico. Dedicated to reframing the concept of aging, MEA supports students in navigating midlife with a renewed sense of purpose and possibility.

Join him IRL at Eudēmonia this fall.

West Palm Beach. November 5–8, 2026.

Chip Conley is on a midlife mission.

After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018 in Baja California, Mexico.

Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world’s first ‘midlife wisdom school’.

The academy opened a campus in 2024 on a 2,600-acre regenerative horse ranch in Santa Fe, New Mexico. Dedicated to reframing the concept of aging, MEA supports students in navigating midlife with a renewed sense of purpose and possibility.

Join him IRL at Eudēmonia this fall.

West Palm Beach. November 5–8, 2026.

Chip Conley is on a midlife mission.

After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018 in Baja California, Mexico.

Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world’s first ‘midlife wisdom school’.

The academy opened a campus in 2024 on a 2,600-acre regenerative horse ranch in Santa Fe, New Mexico. Dedicated to reframing the concept of aging, MEA supports students in navigating midlife with a renewed sense of purpose and possibility.

Join him IRL at Eudēmonia this fall.

West Palm Beach. November 5–8, 2026.

Chip Conley is on a midlife mission.

After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018 in Baja California, Mexico.

Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world’s first ‘midlife wisdom school’.

The academy opened a campus in 2024 on a 2,600-acre regenerative horse ranch in Santa Fe, New Mexico. Dedicated to reframing the concept of aging, MEA supports students in navigating midlife with a renewed sense of purpose and possibility.

Join him IRL at Eudēmonia this fall.

West Palm Beach. November 5–8, 2026.

In this episode, Angus Fletcher, a professor, author, and advisor to U.S. Army Special Operations, explains why so many people feel stuck even when life looks “right,” and what important human abilities we slowly lose as we get older without noticing.

Instead of chasing more knowledge, Angus points to a different path, one built on the natural abilities we all had as children but were slowly trained out of as we grew up.

This conversation doesn’t just explain the problem. It gives you a new way to see your life, your story, and what’s still possible.

🎧 Watch now and reconnect with the part of you that’s been missing. Link in bio to listen!

Missing Baja right now, even though I was there just three days ago. I know I’m gonna have some of my ashes scattered there. Where are you gonna have your ashes scattered?