By Michael McCarthy By Michael McCarthy | July 17, 2024 | People, Feature,
Bestselling author Chip Conley admits he doesn’t have all the answers about aging. But he certainly has a blueprint for living midlife and beyond in bliss.
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Chip Conley (chipconley.com) is one of those guys who instantly feels familiar.
I met him for the first time in March in Palo Alto. He was part of a panel discussion I moderated about the art of pivoting in life and business. The panelists, including an instructor at Stanford Business School and the most successful realtor in the Bay Area, were heavy hitters. But Conley stood out by not standing out. His responses to questions were measured and insightful, with a voice mixing natural wisdom and tech-savvy. The audience loved it and surrounded him after the event, hoping to glean a nugget for learning how to live, grow, prosper and thrive in these interesting times.
Conley’s resume is impressive and eclectic. He launched Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and he was Airbnb’s head of global hospitality and strategy. Conley was even a founding board member at Burning Man. More recently, he created the Modern Elder Academy (@meawisdom), or MEA, dedicated to reframing aging. It has two campuses, one in Santa Fe and another in Baja, Mexico.
New York Times bestselling author is also part of Conley’s resume. He has written A Year of Wisdom; Wisdom @Work; Emotional Equations; PEAK: How Great Companies Get Their Mojo From Maslow; and The Rebel Rules: Daring to Be Yourself in Business.
His latest book, Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age, served as the foundation of our interview. When we chatted on Zoom in early June, he was in Baja. He greeted me with a characteristically broad smile, “Welcome to 100 acres of love,” he said. In more than 25 years of interviews, I’ve never had the first line of a chat begin with this much enthusiasm. Here, Conley discusses everything from the art of aging wisely to his relationship with cancer.
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What are you doing today?
Well, I’m doing what I do on many days. I’m in the thick of things with 20 to 25 people in a workshop, helping them go through the MEA program, which is about navigating transitions, cultivating purpose, learning how to own your wisdom and creating a better relationship with aging. I created the world’s first midlife wisdom school to help people in their 40s, 50s, 60s and beyond.
You have a fascinating take on happiness in middle age.
Start with a social science around the U curve of happiness, showing that adults’ bottoming out of life satisfaction is around 45 to 50. The midlife crisis.
But many people don’t know that starting at age 50, we generally get happier with each decade. I’m not overlooking that many people in the middle of their lives are going through all kinds of transitions—from empty nests to divorce to changing careers. They’re retiring or taking care of their parents. They also have scary health diagnoses, menopause and more.
Navigating transitions is natural. It happens in adolescence and midlife. I call it middle-escence. We have a whole social infrastructure to help adolescents with their transitions, but we have no social infrastructure, schools or tools to help people through midlife.
Until you came along and decided to shake things up.
Well, the answers were more than starting to exercise at 50 or spending thousands of dollars on biohacking.
It’s a mindset shift, and it’s about cultivating purpose. According to the Blue Zones (bluezones.com) research, purpose is one of the most essential variables for people who live longer, healthier and happier lives. We have a three-year partnership with Blue Zones, and we do workshops on our two campuses.
What other factors contribute to midlife happiness?
The second pillar of our program is the idea of owning wisdom. We’re moving out of the knowledge era into the wisdom era.
Peter Drucker, the management theorist who coined the term knowledge workers, said knowledge workers would rule the world. And I guess that’s appropriate for Silicon Valley and the Bay Area. Seven of the 10 most valuable companies in the world today are tech companies, the ultimate place for knowledge workers.
But in the era of AI, knowledge is commoditized. What’s becoming more scarce and valuable is the idea of wisdom. And wisdom isn’t knowing the capital of Paraguay. It’s your life lessons—these are the raw materials of your future wisdom.
At MEA, we host leadership teams and peer-to-peer networks and teach wisdom management practices for more effective teams. It’s an art, and everyone can benefit from it.
What is a modern elder, and how did this phrase become part of your book Wisdom at Work?
I’ll share the origin story of the modern elder. When I joined Airbnb 12 years ago, the founders reached out to me and said, ‘Listen, we’re this little tech startup. We’re growing fast. But we’re disrupting an industry we don’t understand. We’re a tech company that wants to be a hospitality company, but nobody here understands hospitality or travel.’
I was brought in to do some consulting and be the in-house mentor to the founders—just in terms of their leadership and learning the hospitality business.
After I’d been there a few weeks, they said, ‘Chip, we hired you for your knowledge, but what you brought is your wisdom. You’re our modern elder.’
I told them I didn’t want to be their modern elder! They pointed out I was 52, and the average employee was 26. They said, ‘But you’re modern because you’re as curious as you are wise.’
To me, they were pointing out that my job wasn’t about the reverence of an elder. It was about my relevance.
How do people in midlife fit into a work culture in the Bay Area where youth reigns?
HR departments and CEOs now realize that intergenerational collaboration is essential when we have five generations in the workplace for the first time. In the next few years, most Americans will have a boss younger than they are. We’ve never seen this before. It’s happening because digital intelligence and digital natives are rooted in young people. In tech companies, this is even more prevalent, of course.
So, here we are: Many younger people are managing older people. How are we growing their emotional intelligence and leadership skills? One way is to create mutual mentorship; people on both ends of the age spectrum in the workplace learn from each other while fostering respect and motivation.
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You have boundless energy. Is that one of the secrets of midlife success?
The most important thing for anybody to do at any age—whether a job interview or pitch during a big meeting—is to show up with curiosity and passion. If you do this, they won’t notice your wrinkles. They’ll notice your energy.
That’s what people are drawn to. You become a role model for younger people. Another secret weapon we have in midlife is being present. You’re not talking about the future or past. You’re simply there with the other person in the moment. That’s impactful.
What do you mean by midlifers growing whole, not old?
To grow whole is to say you’re all the ages you’ve ever been and will ever be. A particular chronological age or a generation doesn’t define you.
I don’t know about you, but in my 20s, I was very compartmentalized regarding my friendships. As an MBA student, I had Stanford Business School friendships. As a newly out gay man, I had my Castro District friends. I had my work friends. My life was pretty compartmentalized. And that’s very much how we live our 20s, 30s and 40s.
As we get older, we learn to show up with who we are. You’re free to alchemize the polarities of who you are—to be both an extrovert and an introvert, to have both masculine and feminine qualities, to possess gravitas and levity.
As we age, we have enough intuition to understand what the room needs—serious conversation, humor or something else. I could never do that when I was 30.
You’ve talked about the three vaults of conversation in social settings. What does that mean?
It’s how we talk to each other. The first vault contains the facts of our lives. The second includes the stories of our lives. And the third vault contains the essence of who we are and what’s happening now. The best dinner parties or social events are those where you create a safe space for people not to judge and lead with their vulnerability—and people welcome it, even men. So, as a party host, you become a social alchemist. How do you take people to a place where they’re having a unique experience?
You’ve been open about your cancer diagnosis. How has it impacted your worldview?
I’m six years into it now. I found out that I had stage one prostate cancer, and then it went to stage two and, now, stage three. I’ve had my prostate removed, underwent radiation for two months and have been on radiation depletion therapy for 18 months.
You can look at cancer as the thing you’re supposed to kill, or you can look at cancer as your teacher. I’ve chosen the latter, even though I don’t mind seeing bumper stickers that say kill cancer or cancer sucks. But my point of view has been cancer is this: What are you supposed to teach me? I’m open to attending cancer school for a while, but I want to graduate.
Some of the lessons I’ve learned from cancer have been how vital and valuable relationships are, especially family and friends. I’ve also learned to receive help from people. I’m open about vulnerability, and I’m pretty joyous.
When I was going through my radiation, people asked, ‘Chip, can I bring some chicken soup over?’ Usually, I wouldn’t want people to do that for me, even though I love serving others. So, I’ve had to learn that one. I’ve also learned how not to be the hero in my company. I’ve learned how to distribute responsibilities so the MEA world doesn’t revolve around me.
What are you looking forward to?
First, I want to continue to disrupt higher education. A midlife population deserves a new way to navigate and learn. I also want to disrupt retirement communities. MEA now has a residential community in Baja, and we’ll do the same thing in Santa Fe.
I also want to be a great dad. After our chat, I’m heading to the airport to visit my sons, Eli and Ethan, who are 12 and 9. I am their biological father with a lesbian couple who are longtime friends. I hang out with the boys every month. They come to Sante Fe or Baja, or I go to Houston. I love helping them be original and authentic and chart their paths. It’s one of the best jobs I’ve ever had.
Photography by: TRACY EASTON; STYLED BY THERESA PALMER, A PALMER IN CALIFORNIA; PHOTOGRAPHED AT THE FOUR SEASONS, SILICON VALLEY AT EAST PALO ALTO