How to Navigate Mid-life Transitions as a Modern Elder

Chip Conley, MBA

Learn how to expand your wisdom, cultivate a generous culture, invest in mentorship, and thrive in relationships as a leader.

Photo by Lisa Keating

In this Episode of The Human Upgrade™...

… Chip Conley, MBA, talks with Dave in Austin about the concept of wisdom, transcending age boundaries, and the importance of writing down life lessons. He firmly believes that curiosity is the elixir of life.

He also explores the paradigm shift in company culture, where focusing on “cultural add” rather than “cultural fit” can foster innovation and diversity. Drawing on his experience that propelled Airbnb’s success, Chip uncovers how Airbnb maintains its strong cultural focus through cultural values interviews and company-wide gatherings.

A big part of mid-life includes navigating and understanding different generations, especially in the workplace. Chip earned the name “Modern Elder” in a surreptitious way through his work with much younger employees.

He founded Joie de Vivre Hospitality at age 26, transforming an inner-city motel in San Francisco into the second-largest boutique hotel brand in America. He operated that business for more than two decades until he sold it. Airbnb looked to Chip’s sustained success in the hospitality space and asked him to help transform their start-up into the world’s leading hospitality brand more than a decade ago. He came on to lead Global Hospitality and Strategy. Then 52, he was twice the age of the average Airbnb employee. This earned him the title “Airbnb’s Modern Elder” who was as curious as he was wise. He’s currently the company’s Strategic Advisor for Hospitality and Leadership.

That experience influenced Chip to create the Modern Elder Academy—a new roadmap for mid-life and learning opportunities—at an oceanfront campus in Baja California Sur, Mexico.

“What MEA is doing is we’re disrupting retirement communities and we’re disrupting higher education,” he says. “We need long life learning. That’s how you help people to learn how to live a life that’s as deep and meaningful as it is long. So, it’s about the quality and the quantity.”

Chip’s also a New York Times bestselling author, an in-demand public speaker (especially TEDtalks!) and is on the advisory council for the Stanford Center on Longevity.

Ultimately, Chip believes in the importance of embracing a beginner’s mindset, investing in relationships, giving back to the community, and honing leadership skills for a fulfilling and meaningful life journey.

If you want to gain valuable insights on navigating modern leadership, culture, and mid-life transitions, and unlock the wisdom that transcends age, this is the episode for you. 

Watch this episode on YouTube!  


Learn more about Modern Elder Academy at and use code DAVE20 to save 20% off in-person workshops, MEA Online, or Sabbatical Sessions. *Offer valid throughout 2023 (some minor restrictions may apply).

SPECIAL PRESENTATION: Live Fireside Chat: Dr. Mark Hyman & Chip Conley

The universe aligned to bring Dr. Mark Hyman and Chip Conley to Austin to talk with Dave on The Human Upgrade recently. If you missed Mark’s chat with Dave about how to be “Young Forever,” listen here. Then, Dr. Mark and Chip connected for a Live Fireside Chat—listen here!

“In the era of gender fluidity, why not have age fluidity? Age fluidity is the idea.”

Chip Conley, MBA

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  • Wisdom can be acquired at any age and writing down life lessons can be a useful exercise.
  • Companies should focus on cultural add rather than cultural fit.
  • Airbnb has a strong focus on culture and uses a cultural values interview and company-wide gatherings to maintain and build culture.
  • Self-awareness and asking the right questions are important in the hiring process.
  • When seeking a mentor, be specific about what you’re looking for and consider a mutual mentorship where both parties can learn from each other.
  • Midlife is a time of transition and the Modern Elder Academy aims to help people navigate this period.
  • Selective hiring can encourage success and filter out those with bad intentions or envy.
  • Society needs to shift its relationship with aging and invest more in helping people navigate midlife transitions.
  • Disrupting traditional industries such as retirement communities and higher education can be valuable.
  • Embracing being a beginner again, investing in relationships, giving back to the community, and investing in leadership skills are important for a long, happy life.

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