Men vs Women in Midlife: The Struggles No One Warns You About
The Midlife Chrysalis
Intro
Chip Conley and Derek Gale introduce Wisdom Wednesdays and set the episode's midlife focus.
Most people imagine a midlife crisis as sports cars, bad decisions, and dramatic life changes. But what if midlife is actually something much deeper and more meaningful?
In this episode of Midlife Chrysalis, Chip Conley explores what really happens during midlife and why men and women often experience it differently. Chip shares insights from years of research and thousands of midlife transitions, revealing the real challenges people face in their 40s, 50s, and beyond.
In this conversation, you’ll learn:
- Why midlife is often a feeling of being stuck, not a crisis
- The hidden struggles men face, including hormonal decline, loneliness, and loss of purpose
- Why many women experience invisibility and financial pressure in midlife
- How menopause, andropause, and identity shifts reshape relationships and self-confidence
- Why the real question in midlife becomes “How will you invest your wisdom?”
If you’re navigating midlife, or preparing for it, this episode offers a powerful new way to understand this stage of life.
Watch the episode to see how midlife can become a turning point, not a breakdown.
Timestamps:
00:00 Welcome to Wisdom Wednesday
00:30 When Organizations Go Through Midlife
03:17 Change Management vs. Transition Management
05:00 Hormones and Andropause in Men
07:38 Career and Financial Disappointment
08:22 Growing Irrelevance in Midlife
09:20 Male Loneliness and Social Disconnection
10:06 Loss of Purpose After Career Changes
10:47 Low Testosterone and Men’s Health
13:55 Self-Esteem and Midlife Relationships
15:17 The Pain of Becoming Irrelevant
17:23 Menopause and Hormonal Changes for Women
19:34 The Pressure of Conventional Beauty
20:38 Invisibility in Dating and Work
22:04 Financial Challenges for Women
22:55 The Burden of Endless Caregiving
23:34 Hormone Replacement Therapy Debate
26:37 Communication in Relationships
27:19 Final Advice for Navigating Midlife
Learn more about MEA at https://www.meawisdom.com/
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