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

February 16, 2026

AI Summary

5 min read

🎙️ The Voices & The Context

The Format: This is a warm, intimate, and deeply conversational interview. Host Chip Conley guides the guest through his life story, creating a safe space for vulnerability and reflection.
The Key Players:
- Chip Conley: The host, founder of the Modern Elder Academy (MEA), and author. He is empathetic, wise, and acts as a thoughtful sounding board.
- Greg Scheinman: The guest, founder of "Midlife Male" media. He is a 52-year-old former film producer and insurance executive who presents as a hyper-masculine, successful man but is surprisingly open about his insecurities and struggles.
The Vibe: Intensely Vulnerable & Surprisingly Uplifting. The conversation moves from dark moments of professional failure and personal identity crisis to a hopeful, actionable blueprint for reinvention. It feels like a masterclass in "real talk" for men.

🗝️ Key Themes & Topics

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What you'll learn

1 (00:00) **🎙️ Introduction: Greg Scheinman**
2 (02:12) **Greg's Backstory: From Harvey Weinstein to Entrepreneurship**
3 (09:56) **Wisdom on Transitions and the Growth Mindset**
4 (12:14) **The Insurance Career and Identity Crisis**
5 (18:34) **Struggling with Identity and the Dark Night of the Ego**
6 (23:11) **The Parking Lot Moment: Birth of Midlife Mail**
7 (27:02) **Impact on Marriage and Masculinity**

+ Full timestamped outline available in the app

Show Notes

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 Introduction

00:24 Early Life & Family Loss

02:38 Working for Harvey Weinstein

05:03 From Film to Entrepreneurship

08:15 Lessons on Curiosity & Reinvention1

0:53 Identity Crisis at 40

13:29 Entering the Insurance Industry

15:16 Building a PBS Show

16:57 Struggling with Identity

22:20 Tipping Point at 47

24:33 Creating Midlife Male

26:30 Marriage Problems & Masculinity

30:34 Why He Built Midlife Male

38:48 The Modern Midlife Male Dilemma

41:37 Conviction, Curiosity & Courage to Speak

45:00 The Six F’s of Life & Finding Success

49:06 Raising Sons Today

54:56 Wisdom Bumper Sticker

57:07 Learning to Be Both Hard & Soft

Learn more about MEA at ⁠https://www.meawisdom.com/

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