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 lifeIf 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. 

Timestamps:

01:58 Why mentorship matters in midlife

04:16 Digital natives vs digital immigrants

05:11 The respect gap in mentorship

06:20 Defining wisdom and lived experience

07:10 Four stages of becoming a modern elder

08:22 Appreciative inquiry and powerful questions

10:30 Librarian mentor vs confidant mentor

12:20 Chip Conley and Herb Kelleher mentorship story

14:20 How confidant mentorship builds confidence

15:45 How to structure a healthy mentorship

16:53 Mentors vs coaches explained

18:35 The mentorship gap and retention impact

18:51 How to start mentoring at midlife

20:55 Mentorship and renewed purpose

21:51 Final reflections and closing 

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