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
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.
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.
Dec 12, 2025 • 59min
Laird Hamilton & Gabby Reece on Love, Longevity, and Aging with Power
Laird Hamilton, a big-wave surfing legend, and Gabby Reece, a former pro volleyball player and fitness entrepreneur, explore the transformative power of midlife. They dive into their unique island childhoods and how these experiences shaped their athletic journeys. Breathwork emerges as a key training tool, enhancing performance and well-being. They challenge the notion of a midlife crisis and celebrate the growth that comes with aging. Together, they emphasize presence, patience, and the importance of community as they navigate life and family.
12 snips
Dec 10, 2025 • 16min
How Curiosity Fuels a Longer, Healthier Life
Discover how adjusting your mindset about aging can actually extend your life! Research reveals that a positive outlook can add years, while curiosity and lifelong learning serve as the keys to a fulfilling midlife. Dive into the concept of anticipated regret as a motivator, and challenge the belief that you’re 'too old' for new experiences. Explore practical steps to embrace growth and reshape your narrative about aging. It's time to rethink your next chapter!
Dec 8, 2025 • 60min
Marianne Williamson: The Courage to Age, Evolve & Challenge Power
Marianne Williamson, a spiritual author and activist with a focus on feminism and social policy, discusses the transformative nature of midlife. She challenges traditional views on aging, emphasizing that it's a time for spiritual awakening rather than crisis. Marianne reflects on the emotional journey of menopause and the importance of communal rites of passage. She advocates for societal shifts that support aging individuals and encourages women to embrace their 'third chapter' with courage and joy, redefining what it means to grow older.
6 snips
Dec 5, 2025 • 1h
Dan Buettner on Aging Smarter: The Real Secrets of Longevity
Dan Buettner, a longevity researcher and author, delves into the essential habits that can help you live longer and healthier. He reveals why many anti-aging shortcuts fail and how embracing daily movement and purpose can transform your life. Dan tackles America's aging misconceptions and discusses the impact of processed foods and social connections on longevity. He shares insights from his adventurous life and the transformative power of meditation during midlife. Discover how small changes can lead to significant health benefits!
