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
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.
Dec 24, 2025 • 21min
The Success Treadmill Is Real: Here’s How to Escape
In this insightful discussion, Chip Conley, entrepreneur and founder of the Modern Elder Academy, shares his journey through midlife and the emptiness that can follow success. He reveals why chasing achievements often leaves us unfulfilled, emphasizing the distinction between happiness and joy. Chip discusses the power of intentional gratitude practices and how these can transform our perspective on daily life. With personal stories of growth and challenges, he encourages listeners to step off the success treadmill and rediscover what truly matters.
Dec 22, 2025 • 52min
The Hidden Cost of Playing It Safe in Midlife | Dr. Margie Warrell
Dr. Margie Warrell, a global expert on courage and bestselling author, shares her inspiring journey from a rural Australian farm to a life of bravery and reinvention. She discusses the hidden 'timidity tax' of playing it safe in midlife and why staying comfortable can hold us back. Margie emphasizes that courage is a decision rather than an emotion and offers practical strategies to overcome fear, challenge limiting beliefs, and embrace personal growth. Her insights will inspire you to step bravely into new possibilities.
10 snips
Dec 19, 2025 • 57min
Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald
Rachel Greenwald, a veteran matchmaker and Harvard MBA, shares her insights into the challenges of midlife dating. She highlights why traditional dating checklists often backfire and reveals the most powerful question to ask when seeking a partner. Rachel emphasizes the difference between fleeting chemistry and lasting compatibility, urging listeners to embrace unexpected connections. She also discusses modern relationship dynamics, including living apart together, and the importance of broadening dating criteria in this chapter of life.
Dec 17, 2025 • 23min
Inside the Messy Middle: What Actually Drives Transformation in Midlife
Feeling stuck in midlife? You might be in a transformative chrysalis instead. Discover the three stages of transition and why understanding the messy middle is key. Learn how men and women experience midlife differently and the importance of transitional intelligence for clarity. Chip shares insights on embracing a growth mindset and practical exercises to reframe aging positively. Step into your evolution with reassurance and new perspectives on purpose and identity.
Dec 15, 2025 • 1h 2min
Michael Clinton on Life Layering: How to Build a Richer Life After 50
Michael Clinton, a longevity visionary and bestselling author who once led Hearst Magazines, dives into the transformative potential of midlife. He unveils the ROAR framework, urging listeners to Reimagine, Own their age, Act through life layering, and foster meaningful Relationships. Clinton shares his personal adventures, from climbing Kilimanjaro to returning to school at 67, illustrating reinvention at any age. He emphasizes the importance of building diverse identities and supportive relationships for a richer second half of life.
