Stop Playing Small: Chip Conley on Thriving in Your Second Act

In the latest episode of Contracting Conversations, we talk to Chip Conley, hospitality entrepreneur, Modern Elder Academy founder, and bestselling author, to discuss what it takes for contract cleaning pros to thrive in their second act. From leading one of the largest boutique hotel companies in the U.S. to mentoring Airbnb’s founders and creating the world’s first midlife wisdom school, Chip shares lessons on career reinvention, leadership resilience and why curiosity is the ultimate competitive edge.
Chip opens up about the challenges of growth plateaus, the psychology behind entrepreneurial burnout, and strategies to reignite purpose and passion. He also dives into how company culture drives employee retention, why recognition matters more than money, and how wisdom helps navigate complexity in industries like commercial cleaning and hospitality.
Conversation Highlights:
• Ways to break through business growth plateaus and avoiding burnout.
• Paths for mid-career entrepreneurs: sell, delegate, or rediscover purpose.
• How to stay relevant through curiosity and crystallized intelligence.
• Why creating cultures of recognition and meaning can reduce employee turnover.
Chip Conley is co-founder and executive chairman of MEA (formerly Modern Elder Academy) and a renowned entrepreneur, best-selling author, and dynamic speaker celebrated for his innovative approach to leadership and hospitality. As the founder of Joie de Vivre Hospitality, he expanded a single boutique hotel into the second-largest boutique hotel brand in the U.S. In 2013, he joined Airbnb as head of global hospitality and strategy, mentoring its founders and helping shape its culture during a rapid growth phase. Inspired by his midlife journey, experience at Airbnb, and extensive research and collaboration with thought leaders in the area of aging, Chip co-founded MEA, the world’s first midlife wisdom school.