The Midlife Chrysalis
Chip Conley
The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife.
Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.
Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.
Episodes
Mentioned books
8 snips
Jan 28, 2026 • 18min
Why Rituals Matter More Than Routines in Midlife
A conversation about turning mechanical morning routines into small, meaningful rituals that bring calm and purpose. They explore shower meditations, prayer-like mantras, and a stretching plus affirmation practice. The discussion covers habit-stacking to make rituals stick and how to craft specific, emotionally true affirmations. Listeners are invited to try one simple micro-ritual to shift their day.
Jan 26, 2026 • 1h 4min
How Ritual, Awe, and Community Bring Midlife Back to Life | Christine Sperber
Christine Sperber, co-founder of the Modern Elder Academy and master experience designer, blends ritual, community, and nature to reframe midlife as creative renewal. She recounts Baja life, communal bread baking, and designing gatherings that spark awe. Short, vivid stories explore rhythm, belonging, and reclaiming vitality through simple, shared practices.
Jan 23, 2026 • 48min
The Bonus Years: Midlife Is About Reinvention Not Retirement | Pam McLean
Pam McLean, a pioneering coach and psychologist, discusses transformative ideas surrounding midlife. She highlights the importance of letting go of old identities for personal growth and explains the concept of 'bonus years'—redefining midlife as a time for new opportunities rather than retirement. The conversation also delves into how discomfort and curiosity fuel change, the unique approaches of men and women in midlife, and the evolving landscape of coaching, emphasizing the need for genuine connection in selecting a coach.
Jan 21, 2026 • 35min
Midlife Isn’t Falling Apart – It’s a Transformation
Midlife isn’t a crisis; it’s a chance for transformation. Chip Conley explores how happiness dips in midlife but often rises later. He shares personal struggles with identity and burnout, advocating for viewing midlife as a necessary chrysalis. Discover how societal expectations differ for men and women, and the lack of support systems for midlifers. Chip even proposes a midlife sabbatical to help individuals curate a fulfilling second adulthood. Embrace the changes as opportunities for growth and wisdom!
8 snips
Jan 19, 2026 • 58min
Gavin Newsom on Leadership, Identity, and Becoming Yourself
In a revealing conversation, Gavin Newsom, Governor of California and former San Francisco mayor, shares insights shaped by a lifetime of experience. He discusses how his dyslexia and family background influenced his leadership journey. Newsom reflects on the emotional gravity of legalizing same-sex marriage, and how his years as lieutenant governor humbled him. He emphasizes the importance of grace, humility, and resilience, as well as the role of fatherhood in shaping authenticity and acceptance during midlife.
10 snips
Jan 16, 2026 • 1h 5min
He Had Everything. Midlife Broke Him Anyway | Blake Mycoskie
Blake Mycoskie, founder of TOMS Shoes and advocate for mental health, shares his journey through a profound midlife crisis. He candidly discusses how selling TOMS led to an identity collapse, revealing that midlife depression often follows success. Blake explores transformative treatments like ketamine therapy and emphasizes the importance of connection in overcoming struggles. His breakthrough realization of being 'enough' inspired the 'I Am Enough' initiative, aiming to foster mental health awareness and support among youth.
17 snips
Jan 14, 2026 • 28min
Could Golden Girls–Style Living Be the Future of Midlife Housing?
Chip Conley, founder of Modern Elder Academy and a hospitality entrepreneur, delves into the innovative concept of Golden Girls-style living aimed at combatting loneliness among solo agers. He discusses the rise of gray divorce and its impact on women's housing situations. Conley explores why traditional housing models no longer meet midlife needs and shares insights from his Santa Fe pilot project. With a focus on community and connection, he shares strategies for roommate matching and long-term affordability—reimagining how we can thrive in our later years.
Jan 12, 2026 • 59min
Aging While Black: Paying the Price of a Broken System | Ray Jetson
In this engaging discussion, Ray Jetson, a pastor, former Louisiana legislator, and author of Aging While Black, reveals the distinct challenges faced by Black individuals as they age in America. He introduces vital strategies such as the village concept, rooted in African traditions, and the significance of technology for elders. Jetson underscores the importance of mutual mentorship through the Sankofa philosophy, and advocates for collective longevity across generations. This conversation inspires fresh insights on aging, equity, and community care.
Jan 9, 2026 • 1h 2min
How Conscious Capitalism Changes the Way Leaders Think | Rand Stagen
Rand Stagen, Founder of the Stagen Leadership Academy and a pioneer in Conscious Capitalism, shares transformative insights on leadership. He emphasizes the pitfalls of short-term thinking and advocates for players in the infinite game of leadership. Stagen explains the importance of awareness in decision-making, stating that great leaders think in decades, not quarters. He also delves into integral theory, encouraging leaders to navigate societal polarization and pursue deeper meaning in their work. His mantra: true leadership starts from within.
Jan 7, 2026 • 28min
Why Leadership Fails When Wisdom Walks Out
Leaders are racing toward efficiency but risking their edge: wisdom. Discover how true leadership is a practice shaped by culture and lived experiences. Learn about the alarming loss of institutional wisdom and the critical difference between knowledge workers and wisdom workers in the AI era. Chip emphasizes the value of personal connections, informal mentors, and self-leadership. With technology rising, the demand for humanities in ethical decision-making is making a comeback, proving that human skills are the new competitive advantage.
