Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman episode artwork

EPISODE · Feb 16, 2026 · 1H 3M

Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman

from The Midlife Chrysalis · host Chip Conley

Ever wonder what happens when “success” still feels empty?At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself and create Midlife Male, a movement helping men find purpose, strength, and authenticity in midlife.In this episode, we dive into what modern masculinity really means, why so many men struggle with identity and purpose, and how to turn a midlife crisis into a life by design. Tune in to learn how Greg turned breakdown into breakthrough and how you can too. Timestamps:00:00 Introduction00:24 Early Life & Family Loss02:38 Working for Harvey Weinstein05:03 From Film to Entrepreneurship08:15 Lessons on Curiosity & Reinvention10:53 Identity Crisis at 4013:29 Entering the Insurance Industry15:16 Building a PBS Show16:57 Struggling with Identity22:20 Tipping Point at 4724:33 Creating Midlife Male26:30 Marriage Problems & Masculinity30:34 Why He Built Midlife Male38:48 The Modern Midlife Male Dilemma41:37 Conviction, Curiosity & Courage to Speak45:00 The Six F’s of Life & Finding Success49:06 Raising Sons Today54:56 Wisdom Bumper Sticker57:07 Learning to Be Both Hard & Soft Learn more about MEA at ⁠https://www.meawisdom.com/#GregScheinman #MidlifeMale #MidlifeChrysalisPodcast #ChipConley #ModernMidlifeMan #MenInMidlife #MidlifeReinvention #MidlifeIdentity #MensMentalHealthAwareness #RedefiningMasculinity #LifeByDesign #EntrepreneurInMidlife #MidlifeWisdom #PurposeBeyondSuccess #FromCrisisToGrowth

Ever wonder what happens when “success” still feels empty?At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself and create Midlife Male, a movement helping men find purpose, strength, and authenticity in midlife.In this episode, we dive into what modern masculinity really means, why so many men struggle with identity and purpose, and how to turn a midlife crisis into a life by design. Tune in to learn how Greg turned breakdown into breakthrough and how you can too. Timestamps:00:00 Introduction00:24 Early Life & Family Loss02:38 Working for Harvey Weinstein05:03 From Film to Entrepreneurship08:15 Lessons on Curiosity & Reinvention10:53 Identity Crisis at 4013:29 Entering the Insurance Industry15:16 Building a PBS Show16:57 Struggling with Identity22:20 Tipping Point at 4724:33 Creating Midlife Male26:30 Marriage Problems & Masculinity30:34 Why He Built Midlife Male38:48 The Modern Midlife Male Dilemma41:37 Conviction, Curiosity & Courage to Speak45:00 The Six F’s of Life & Finding Success49:06 Raising Sons Today54:56 Wisdom Bumper Sticker57:07 Learning to Be Both Hard & Soft Learn more about MEA at ⁠https://www.meawisdom.com/#GregScheinman #MidlifeMale #MidlifeChrysalisPodcast #ChipConley #ModernMidlifeMan #MenInMidlife #MidlifeReinvention #MidlifeIdentity #MensMentalHealthAwareness #RedefiningMasculinity #LifeByDesign #EntrepreneurInMidlife #MidlifeWisdom #PurposeBeyondSuccess #FromCrisisToGrowth

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Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman

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This episode was published on February 16, 2026.

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Ever wonder what happens when “success” still feels empty?At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself and create Midlife Male, a movement helping men...

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