Episode 70

February 18, 2026

Chip Conley

Why Midlife Friendships Stop Working & How to Fix Them

Why Midlife Friendships Stop Working & How to Fix Them

Ever notice how some friendships don’t end, they just stop deepening?

You still care about each other, but the conversations feel thinner than they used to. In midlife, that quiet shift is more common than we admit.

In this Wisdom Wednesday episode, Chip Conley, founder of MEA, joins Derek Gehl for a warm, honest conversation about friendship in the second half of life: why it changes, why it matters more than ever, and how it can grow again.

What you’ll take away:

  • Friendship is a practice, not a personality trait
  • Most of us outgrow conversations, not people
  • Depth and vulnerability create real connection
  • Reaching out — even after years — can reopen meaningful bonds

If you’ve ever wondered how to build friendships that actually nourish you as you age, this conversation is for you.

👉 Listen now and discover how midlife friendships can become richer, not smaller.

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