Episode 67

February 11, 2026

Chip Conley

What Great Mentors Do Differently in Midlife

What Great Mentors Do Differently in Midlife

Most of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions.

In this Wisdom Wednesday episode, Derek and Chip explore how mentorship evolves when experience meets curiosity. Drawing on stories from Airbnb, intergenerational leadership, and lessons from unlikely teachers, Chip shows why the best mentors are still learning.

In this conversation, you’ll discover:

  • Why great mentorship is a two-way exchange, not top-down advice
  • How modern elders learn alongside younger generations
  • The difference between a librarian mentor and a confidant mentor
  • Why respect and curiosity matter more than credentials
  • How asking the right questions creates real growth at work and in life

If you’re navigating midlife, leading across generations, or rethinking how you share your wisdom, this episode is for you.

👉 Watch now and join us for Wisdom Wednesday.

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