Chip Conley on the Coaching Wisdom of the Modern Elder

For the midpoint of Season 3, Kavitha is joined by midlife expert Chip Conley, founder of the Modern Elder Academy. Chip’s exceptional career led him from founding Joie de Vivre Hospitality to serving as Head of Global Hospitality and Strategy for Airbnb during the company’s crucial rise from startup to household name. Chip’s leadership frequently placed him in the role of coach, mentor, and what his colleagues variously described as “confidante” and “modern elder.” Join us to hear Chip’s insight into how midlife mentors can embody both wisdom and curiosity, as well as his perspective on what the historic five-generation span in the workplace means in the contexts of coaching and vocational purpose. In addition, Chip and Kavitha discuss the importance of joy in career and personal success, the contemporary landscape for approaches to leadership, and why Chip believes that life only gets better as we age.

Transcript

S3Ep5—Chip Conley Transcript (AI-generated, unedited)

Links and Resources

Information on YGELP and Yale SOM Executive Education:

Yale SOM Executive Education Homepage

Certificate in Professional Coaching Program Homepage

Resources and Links Mentioned in Today’s Episode:

Modern Elder Academy Homepage

Chip’s Blog: Wisdom Well

Chip’s Podcast: Midlife Chrysalis

Chip’s TED Talks

Mary Catherine Bateson, coiner of “the midlife atrium”

Wisdom at Work: The Making of a Modern Elder by Chip Conley

The Catcher in the Rye by J. D. Salinger

Appreciative Inquiry: A Positive Revolution in Change by David Cooperrider and Diana Whitney

One Person/Multiple Careers: A New Model for Work/Life Success by Marci Alboher

More about Dilip Jeste’s Wisdom Scale

Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age by Chip Conley

Dr. Becca Levy, Professor of Public Health with the Yale School of Public Health

The Mature Mind: The Positive Power of the Aging Brain by Gene Cohen

From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life by Arthur Brooks

Generations: The Real Differences Between Gen Z, Millennials, Gen X, Boomers, and Silents—and What They Mean for America’s Future by Jean Twenge

Peak: How Great Companies Get Their Mojo from Maslow by Chip Conley

The Ezra Klein Show

Interesting Times with Ross Douthat

About Today’s Guest

Chip Conley is on a midlife mission. After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018 in Baja California, Mexico. Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world’s first ‘midlife wisdom school’ and has a 2,600-acre regenerative horse ranch in Santa Fe, New Mexico which opened in May 2024. Dedicated to reframing the concept of aging, MEA supports students to navigate midlife with a renewed sense of purpose and possibility. Conley has authored eight books, given three TED talks, has a daily Wisdom Well blog, and a weekly podcast The Midlife Chrysalis which has included a wide variety of guests from Maria Shriver to Arthur Brooks to Elizabeth Gilbert to Rich Roll.