At age 26, Chip Conley founded Joie de Vivre Hospitality and grew the company into the second largest boutique hotel brand in the United States. After he sold the business, he accepted a strategy role at Airbnb, and his interactions with a predominantly millennial workforce led him to found the Modern Elder Academy, a “midlife wisdom school” in Baja that encourages individuals with a lifetime of experience to carve a purposeful path through the modern workplace. Here, he shares the insights that have allowed him to flourish while shifting roles and accommodating to cultural change.