The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half

The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half

Chip Conley is a hospitality maverick, founder of Modern Elder Academy, and the entrepreneurial sage who helped transform Airbnb from a startup to a global phenomenon. This conversation explores midlife as a chrysalis rather than a crisis—a transformative journey from ego to soul. Chip illuminates the path from horizontal achievement to vertical growth, addressing life's longest yet least understood phase. We discuss his near-death experience, the nature of wisdom, and why friendship becomes essential to wellness as we age. In the process, Chip creates space for me to reflect honestly on my own lifelong pursuit of achievement. Chip is a treasure. This exchange is for anyone seeking to avail themselves of midlife's deeper possibilities. Enjoy! Note: Chip and I invite you to experience these insights in person in Los Angeles on June 5th for a special gathering with the MEA faculty. Register at meawisdom.com/richroll. Show notes + MORE Watch on YouTube Newsletter Sign-Up

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Bruce Wagner Writes Transgressive Novels About Tragedy & Transcendence

Bruce Wagner Writes Transgressive Novels About Tragedy & Transcendence

Bruce Wagner is a novelist, former student of Carlos Castaneda, and author of fifteen books, including his latest, "Amputation." This conversation explores his use of Hollywood as a laboratory for hu...

29 Jan 2h 2min

Decoding Women's Health: Dr. Elizabeth Poynor On Midlife Hormonal Changes, Interventions That Actually Work, & Why Medicine Left Women Behind

Decoding Women's Health: Dr. Elizabeth Poynor On Midlife Hormonal Changes, Interventions That Actually Work, & Why Medicine Left Women Behind

Dr. Elizabeth Poynor is a gynecologic oncologist, Chair of Women's Health at Atria Health Institute, and host of the podcast “Decoding Women's Health.” This conversation explores why women's health h...

26 Jan 1h 32min

Reclaim Your Excellence: The Path To A Meaningful & Joyous Life w/ Brad Stulberg

Reclaim Your Excellence: The Path To A Meaningful & Joyous Life w/ Brad Stulberg

Brad Stulberg is a bestselling author, executive coach, and one of my favorite thinkers on sustainable high performance. This conversation explores the dualities in personal development, discipline a...

19 Jan 2h 3min

Cognitive Scientist Maya Shankar On Navigating Unexpected Life Changes, The Neuroscience Of Identity, & How To Unlock Your Next Self

Cognitive Scientist Maya Shankar On Navigating Unexpected Life Changes, The Neuroscience Of Identity, & How To Unlock Your Next Self

Dr. Maya Shankar is a cognitive scientist, host of the podcast “A Slight Change of Plans,” and author of “The Other Side of Change.” This conversation explores the challenge of navigating involuntary...

15 Jan 2h 6min

Dr. Will Bulsiewicz: Heal Your Gut, Reduce Inflammation & Optimize Your Microbiome

Dr. Will Bulsiewicz: Heal Your Gut, Reduce Inflammation & Optimize Your Microbiome

Dr. Will Bulsiewicz is a gastroenterologist, one of the world's foremost authorities on the gut microbiome, and author of “Plant Powered Plus.” This conversation explores the gut-immune connection as...

12 Jan 2h 27min

Mark Manson On Vanity Goals, Self-Sabotage & How To Actually Change Your Life

Mark Manson On Vanity Goals, Self-Sabotage & How To Actually Change Your Life

Mark Manson is the author of The Subtle Art of Not Giving a F*ck and host of the Solved podcast. Back for his third appearance (eps. 476, 882), we skip the backstory and pull questions from a fishbow...

5 Jan 1h 48min

Best of 2025 (Part Two): The Year’s Most Enduring Insights

Best of 2025 (Part Two): The Year’s Most Enduring Insights

The finale is here. Let's close this thing out. Part 2 explores courage, honesty, creativity, relationships, and balance. Bravery. Addiction. Love. Mastery. And why fulfillment doesn't require sacrif...

29 Dec 20251h 51min

Best of 2025 (Part One): Conversations That Shaped Us

Best of 2025 (Part One): Conversations That Shaped Us

Happy holidays from the RRP mothership. Another year in the rearview. Time for what's become one of my favorite traditions, our annual “Best Of.” 12 years running now. This year was packed with an a...

22 Dec 20251h 46min

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