The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half

Chip Conley is a hospitality maverick, founder of Modern Elder Academy, and the entrepreneurial sage who helped transform Airbnb from a startup to a global phenomenon. This conversation explores midlife as a chrysalis rather than a crisis—a transformative journey from ego to soul. Chip illuminates the path from horizontal achievement to vertical growth, addressing life's longest yet least understood phase. We discuss his near-death experience, the nature of wisdom, and why friendship becomes essential to wellness as we age. In the process, Chip creates space for me to reflect honestly on my own lifelong pursuit of achievement. Chip is a treasure. This exchange is for anyone seeking to avail themselves of midlife's deeper possibilities. Enjoy! Note : Chip and I invite you to experience these insights in person in Los Angeles on June 5th for a special gathering with the MEA faculty. Register at meawisdom.com/richroll . Show notes + MORE Watch on YouTube Newsletter Sign-Up