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
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.
9 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.
16 snips
Jan 5, 2026 • 59min
From Breakdown to Wholeness: The Hero’s Path Through Midlife with Ben Katt
Ben Katt, a former pastor turned meditation teacher and author, shares his insights on navigating midlife transformation. He emphasizes the importance of letting go of familiar identities to make space for deeper purpose. Ben discusses the three phases of the Hero's Journey, including facing the 'dark night of the ego' and the necessity of community support during transitions. He highlights the role of stillness and meditation in achieving inner balance and offers wisdom on cultivating purpose beyond traditional roles.
Jan 2, 2026 • 1h 2min
Jeff Krasno & Schuyler Grant: What Midlife Health Really Requires
In a captivating discussion, wellness entrepreneurs Jeff Krasno and Schuyler Grant share transformative insights on midlife health. Jeff, known for co-founding Wanderlust, highlights the vital role of muscle in metabolism and brain health. Schuyler, a yoga leader, reveals the limitations of yoga alone, stressing the need for diverse, strength-focused movement. They explore habits that foster well-being and the importance of lifelong curiosity. Their grounded advice encourages listeners to rethink wellness approaches as they age.
Dec 31, 2025 • 15min
Stop Starting Over: How to Build Habits That Actually Last
Why do New Year’s resolutions fizzle out by February? Discover the common pitfalls that derail good intentions. Learn about habit stacking to turn changes into daily routines effortlessly. Explore the 'Four Ps' framework that helps make goals stick, along with the power of public accountability. Find out why focusing on fewer goals is often more effective. Dive into personal stories about health, family commitments, and the importance of mindfulness. Transform resolutions into lasting habits that'll carry you through the year.
10 snips
Dec 29, 2025 • 51min
Why Transitions Break Us and Heal Us | Kari Cardinale
Kari Cardinale, Chief Content Officer at Modern Elder Academy, brings a wealth of knowledge on navigating life's transitions. She explains why many midlife crises are actually misunderstood transitions. Listen as she outlines the three stages: endings, the messy middle, and new beginnings. Kari discusses the importance of rituals to mark these changes and introduces the concept of 'glimmers'—small signals guiding us toward new directions. Her insights on Transitional Intelligence offer clarity for anyone feeling stuck in this pivotal life phase.
Dec 26, 2025 • 50min
From Skateboarding Icon to Modern Elder: Stacy Peralta
Stacy Peralta, a legendary skateboarder turned filmmaker and painter, shares his journey from skateboarding to filmmaking, emphasizing the importance of following passion over security. He discusses how past identities can hinder future growth and highlights the power of vulnerability and embracing the role of a beginner. Stacy explains the significance of intuition in navigating life's transitions and shares daily practices to maintain creativity and vitality. His insights on letting go of past selves are both inspiring and liberating.
