Midlife Chrysalis with Chip Conley

In this episode, I explore what happens when midlife brings everything I’ve avoided into sharp focus. Joined by Rebecca Rusch, a world-class endurance athlete, I dive into how the busyness of our 20s and 30s can mask deeper issues, yet midlife inevitably demands that we slow down and look inward. We discuss how pain that goes unaddressed doesn’t disappear—it resurfaces in habits, relationships, and daily life. Together, we unpack why facing discomfort is the first step toward real change, and how midlife can become the most transformative chapter yet.