The New Age of Wisdom: The Rise of a Modern Elder with Chip Conley

Chip Conley at the CultureLab podcast

This month, we’re pulling back the curtain on something we’ve all felt but rarely discuss openly: the tension and challenges of a multigenerational workforce.

Picture your workplace for a moment. Got a few Boomers who can recall the company’s “good old days”? Check. Some Gen Xers who are adept at translating between analog and digital? You bet. Millennials craving a side of purpose with their paychecks? Absolutely. And don’t forget those fresh-faced Gen Zers who’ve been swiping screens since they could walk.

It’s a melting pot of ages and attitudes. Great for diversity but also ripe for conflict. You’ve got folks sending carefully crafted emails while others dash off instant messages like they’re tossing confetti.

This isn’t just about decoding emojis or navigating Zoom etiquette. It’s bigger than that. It’s about creating a place where everyone—regardless of when they were born—feels like they belong, where they’re set up to do their best work. A place where experience is respected, but innovation isn’t stifled. A place where everyone is heard, both the sage veterans and the eager newcomers.

So let’s roll up our sleeves and tackle this head-on. Trust me, whether you’re leading the charge in the C-suite or just punching the clock, you’re going to want to stick around for this one.

Kicking off the series is Chip Conley, who co-founded MEA (Modern Elder Academy) in January 2018, 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.

He is the author of many best-selling books and his latest book, “Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age,” will be released in January 2024.

For Chip, in a world that venerates the new, bright, and shiny, many of us are left feeling invisible, undervalued, and threatened by the “digital natives” nipping at our heels. But he argues that experience is on the brink of a comeback.

Join this week’s episode of the CultureLab podcast, as we break down the notion of intergenerational dynamics and ageism in the workplace.

We are so thrilled to explore Chip’s dedication to reframing the concept of aging and its implications for the future of work.

Episode highlights

Embracing identity and burdens of being the “other.” Chip’s experience as a white man in non-white environments and as a closeted gay man has taught him the importance of being aware of and understanding the perspectives of others, even when they are in the majority.

Democratizing company culture. Culture needs to be democratized, with everyone feeling like they’re a part of it, and avenues for employees to talk about what they want the company to do.

Becoming a modern elder. Chip’s notion of a “modern elder” reflects his transition from being the CEO of his own company to becoming a mentor and intern at Airbnb. The key attributes of a modern elder, include:

  • Curiosity.
  • The ability to make wisdom relevant.

Mentoring privately, interning publicly. For leaders, it’s important to offer feedback and guidance privately to avoid embarrassment, while intern-like questions in public settings can uncover blind spots and fresh perspectives.

Fostering a culture of mentorship and lifelong learning.

Organizations need to promote a mindset of mentorship and continuous learning, particularly for older employees.

Chip created the Modern Elder Academy in response to the need for companies to invest in the development of their midlife and tenured employees. In order to support employees in staying relevant and sharing their wisdom, we need to provide learning sabbaticals and tailored development opportunities every five years.

Mutual mentorships drives retention.

Intergenerational mentorship can become a huge asset. Deloitte’s research is cited to illustrate how millennials are more likely to stay in a company when they have an in-house mentor. So, the role of mentorship in knowledge exchange and employee retention ultimately benefits the organization.

Evolving perspectives on midlife and aging.

The notion of midlife and aging is constantly evolving. Nowadays, people perceive midlife way differently, the potential for greater happiness after the age of 50 is being unfolded. This is why society and companies need to adapt to the changing demographics in the workplace and start supporting individuals to navigate midlife transitions.

The three stages of transitions.

We need to understand and navigate life transitions, particularly the three stages of transitions:

  • Ending.
  • The messy middle.
  • The beginning of something new.

We discuss how individuals can cope with transitions, including the importance of ritualizing endings, seeking social support during the messy middle, and adopting a growth mindset when beginning something new.

Embracing pro-aging and the positive aspects of aging.

Chip’s upcoming book, “Learning to Love Midlife,” includes the 12 reasons why life gets better with age such as: appreciating one’s own counsel, emotional intelligence, time affluence, and shifting from anti-aging to pro-aging perspectives.

Cancer as a teacher and shifting perspectives.

Chip’s personal journey with prostate cancer reshaped his outlook on life and aging. We need to start viewing our body as a best friend and shift from focusing on external appearances to internal well-being. Health challenges can show us the way of mindfulness and of living in the present moment.

Balancing health challenges and career.

Individuals face many dilemmas when dealing with health diagnoses, such as cancer, while navigating their careers. This is why it’s important to start taking care of our health and strike a balance between work and self-care. Sometimes health diagnosis can prompt individuals to reevaluate their career choices and prioritize what truly brings them joy and fulfillment.

Returning to work and sharing wisdom.

One step of the process of returning to work after a health challenge can be to share the lessons learned from our experiences, both personally and professionally, with our colleagues and employers. Painful life lessons can be transformed into wisdom and growth can be seen as a valuable asset to bring back to the workplace and an opportunity to connect.

Listen to the interview in the player below or on iTunes. If you like what you hear, please leave a review, and it may be featured on a future episode.

More about Chip Conley

Chip Conley is on a 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.

Inspired by his experience of intergenerational mentoring at Airbnb – where they called him a “modern elder” and his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, Chip created the world’s first “midlife wisdom school.” Dedicated to reframing the concept of aging, MEA engages and supports students to navigate midlife with a renewed sense of purpose and possibility. With nearly 3,500 alumni from 42 countries and 26 regional chapters globally, MEA is expanding to the United States with a new campus and regenerative community in Santa Fe, New Mexico (slated to open in 2024).

Conley is also the award-winning author of the New York Times bestseller “Emotional Equations,” alongside “Peak: How Great Companies Get Their Mojo from Maslow,” “The Rebel Rules,” “Marketing That Matters,” and “Wisdom at Work: The Making of a Modern Elder,” which forms the core of the MEA curriculum. Conley’s book “A Year of Wisdom” released in May 2023 and is based on daily inspiration and insight from his Wisdom Well blog. His next book,”Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age,” will be released in January 2024.

A hospitality veteran, Conley is the recipient of its highest honor, the Pioneer Award, and was named the Most Innovative CEO in the San Francisco Bay Area by the San Francisco Business Times. He is the founder of the Celebrity Pool Toss that supports families in the Tenderloin neighborhood where he opened his first hotel, and San Francisco’s Hotel Hero Awards. Chip holds a BA and MBA from Stanford University, and an honorary doctorate in psychology from Saybrook University. He serves on the board of, and the advisory board for the Stanford Center on Longevity.

Books mentioned in this episode

Learning to Love Midlife by Chip Conley

Man’s Search for Meaning by Viktor Emil Frankl

Wisdom at Work by Chip Conley

From Strength to Strength by Arthur C. Brooks

People mentioned in this episode

Carol Dweck

Becca Levy

Laura Carstensen

Additional resources

CultureBrained® Community – a one-of-a-kind virtual community for Heads of Culture, founders, and leaders who want to up their culture game.

The Culture Playbook Guide.

Discover Your Personal Values.

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