chip Conley

Wise Eyes, Fresh Eyes

Chip Conley, one of the execs behind Airbnb’s rise, is on a quest to help people restart their careers—and end the office generation gap as we know it. Step one: Stop thinking in terms of “old people” and “young people.”

It was 2013, and Chip Conley was excited for his first day of work at Airbnb. He had a new set of challenges, a whip-smart boss, and an opportunity to help guide one of the country’s most innovative and fastest-growing companies.

Conley was intimidated, too. As the founder of the Joie de Vivre boutique hotel chain, he had a proven track record as a businessman and entrepreneur. But he had never worked in tech. He didn’t know how to use Google Docs. He didn’t even have the apps for Uber or Lyft on his phone. At 52, Airbnb’s new head of global hospitality and strategy was twice the age of the company’s average employee and reported to a boss, CEO Brian Chesky, who was 21 years his junior.

Early on, Conley sat in on a meeting of engineers, hoping to learn the lingo. He planned only on listening and hovered in the background. But then the 25-year-old engineer who was leading the meeting turned to Conley and asked, “If you shipped a feature and no one used it, did it really ship?”

Conley was stumped. He didn’t know what the engineer meant. “It was a classic moment, of, ‘I don’t know what the hell you’re talking about and maybe I’m in the wrong company,’” he says now, sitting in a meeting room at Airbnb’s San Francisco headquarters. “It was not my natural habitat.”

It presented him with a choice. He could back away from Airbnb and return to the rewards of semiretirement. Or he could adapt and change. 

Conley chose the latter. He decided that there was much he could learn from his younger colleagues. They could share with him their “digital intelligence,” the deep and intuitive understanding of technology that comes at least in part from having been raised on computer screens. In turn, Conley could offer them the emotional intelligence he had gained over the years. He knew how to read emotions, manage people, and create a healthy, supportive work environment. His “wise eyes” needed the “fresh eyes” at Airbnb, and vice versa. Conley started to consider himself both an intern and a mentor, or what he calls a “mentern.”

He realized that he was filling a new role, which he came to label as that of a modern elder. Although Conley was only in his 50s—hardly a senior citizen—he was an elder at Airbnb. He wanted to distinguish this new notion from the traditional idea of an older sage who bestows wisdom upon younger people. A modern elder, he says, must also act as a wisdom-seeker.

Conley found his Airbnb experience so energizing that it led him to his next calling: creating a new generational contract in the workplace, in which everyone is valued, no matter their age. “We have five generations in the workplace for the first time,” Conley says. “Instead of power being distributed in the traditional physics of wisdom—from the top down, old to young—the wisdom is now going in both directions.” 

Conley has written a book, Wisdom at Work: The Making of a Modern Elder, part manifesto, part playbook, for people trying to stay relevant in the second half of their careers. And in November, he opened the Modern Elder Academy, which he calls the world’s first midlife wisdom school. A beachfront sanctuary in Baja California Sur, Mexico, it’s a place where people (most between the ages of 45 and 65) can learn to navigate midlife transitions and, as Conley says, “Grow whole, not old.”

His message is timely. The number of working Americans 55 and older has grown over the past decade, from more than 17 percent of the workforce in 2007 to about 23 percent in 2017, according to the Pew Research Center. With advances in health care, we’re also living longer than ever before. The average life expectancy in the U.S. was about 79 years in 2016. Some of us may live 30 years longer than our great-grandparents—and may spend much of that time working.

At the same time, corporate power has shifted younger, resulting in what Conley calls an “irrelevance gap,” in which older workers want to or need to continue working but are afraid that their skills are no longer relevant in the increasingly fast-paced tech world.

According to a 2014 Harvard Business Review study, the founder of a “unicorn”—a tech company valued at more than $1 billion—is, on average, just over 31 years old. Tech is coming to dominate corporate culture, with six of the S&P 500’s top 10 companies specializing in technology. To put it in human terms: Facebook founder Mark Zuckerberg is 34.

“The long story short is that if power is moving 10 years younger and we’re living [at least] 10 years longer, we have a minimum of a 20-year irrelevance gap,” Conley says. For people who have not saved enough for retirement, the economic impact of this gap can be stark.  

Martha Deevy, associate director of the Stanford Center on Longevity, says there is a relatively low unemployment rate among workers aged 60 to 65—but if older workers lose their jobs, it can take them up to three times longer to find a new one than it would take a younger person. “One of the things we’re seeing in the data is that people want to work longer than they are actually working,” Deevy says.

Conley’s solution: Embrace personal and professional growth in order to stay relevant, while creating a workplace that values the viewpoints of different age groups, and lets generations learn from one another.

Chip Conley at TED2010, Session 11, “Simplicity,” Saturday, February 13, 2010, in Long Beach, California. Photography courtesy of TED / James Duncan Davidson

Conley is especially fit to foster a conversation about bringing an open-minded attitude to personal reinvention, and about the bridgeable gap between generations.

A lifelong meditator at 58, he exudes a calm but vibrant energy. He is possessed by a curious intellect, and, in conversation, jumps from heady academic studies to the poetry of Rumi to the soul-searching work of psychologist Viktor Frankl without taking a breath. He’s a longtime devotee of Burning Man, the countercultural gathering in the Nevada desert, and serves as a member of the event’s board of directors. A California native, today he splits his time among San Francisco, El Pescadero, Mexico, and Austin, Texas.

There’s a quote he likes, which he once heard from an executive recruiter and now seems to embody. Paraphrased: “If you are curious and passionately engaged, somehow your wrinkles evaporate.” 

Long before Airbnb, Conley was a young Bay Area disruptor himself, founding Joie de Vivre in 1987, after receiving his bachelor’s degree and MBA from Stanford. Even though, at 26, he knew nothing about the hotel business, he bought a pay-by the-hour motel in San Francisco’s seedy Tenderloin district and transformed it into a rock ’n’ roll-themed destination, The Phoenix. David Bowie came to stay, as did Linda Ronstadt and Johnny Depp.

Conley then opened 51 more properties, each of them unique, quirky, and—unlike many other boutique hotels—affordable. Under Conley’s guidance, Joie de Vivre became the second-largest independent boutique hotel brand in the U.S.

The financial crisis of 2008, however, took an emotional and financial toll. He sold the company in 2010. He planned to move to El Pescadero, and to semiretire. He learned to surf. He started Fest300, an evolving guide to the top 300 festivals in the world, which has since been acquired by Everfest.

He felt adrift, though, until Airbnb CEO Brian Chesky and his two youthful co-founders came calling in 2013. Chesky had read Conley’s book, Peak: How Great Companies Get Their Mojo From Maslow. Airbnb was already a tech darling. But the founders wanted to expand into a full-service hospitality company. They needed an experienced hotelier’s help. 

Conley was asked if he’d work 15 hours a week. That quickly became 15 hours a day, as the business grew and Conley and Chesky mentored each other. They spent weekends in Conley’s San Francisco backyard, sharing insights. Chesky taught Conley about the cultural trends driving younger generations, about the staggering pace at which unicorns grow, and about the needs of Silicon Valley investors. Conley counseled Chesky on managing people. Once, when Chesky had worked his executive team particularly hard, Conley suggested that the CEO send gifts to their spouses, to recognize the sacrifices they had made—thank-you notes for the families, along with a bottle of wine or flowers.

Both men were invigorated by the mutual mentorship and by their embrace of the “beginner’s mind,” a Zen Buddhist concept that, in short, encourages openness and the acceptance of new ideas, free of preconceptions. It’s similar in some ways to the growth mindset described by Stanford psychologist and motivation researcher Carol Dweck, whose work has been an inspiration to both Conley and Chesky.

“There are people who believe that your potential is unlimited, that who you are is not fixed, and that you can evolve and grow,” says Chesky, now 37. “These are people with growth mindsets. I think Chip and I just had that worldview, that we can constantly have a growth mindset at any age.”

Conley relates a story about the 27-year-old woman who was his direct report in the hospitality department at Airbnb. She once told him how he’d influenced the company. Much of Conley’s hotel knowledge—for example, how many rooms a maid can clean in an eight-hour shift—was useless. But because he understood people, he understood how to get things done, she told him. If the company needed to make a change, Conley could identify the three people at Airbnb who needed to know first. That kind of knowledge proved invaluable to the young company. 

Jaja Jackson, 45, Airbnb’s director of global multifamily housing partnerships, says Conley was effective because he listened to his younger colleagues and valued their opinions. “Chip made it very clear that he was not interested in always being the smartest person in the room, so he was able to bring a certain amount of humility into any conversation,” Jackson says. “What he did was empower other people around him to ask questions and be teachers, when they might have otherwise yielded a bit to Chip’s reputation and robbed him of the chance to learn.” 

Conley’s collaborative approach paid off. During the four years he worked full-time at the company (he’s now a part-time consultant), Conley developed Airbnb for Work, which more than 700,000 businesses use for travel. He created new quality standards that all Airbnb hosts had to honor, resulting in guest satisfaction reviews that surpassed those of the hotel industry. He also expanded the company’s Superhost program, for the company’s most experienced hosts, from 200 to nearly 500,000 hosts around the globe. 

It was a transformative experience, one that Conley hopes to cultivate for others at his Modern Elder Academy.

While it may be a big leap from corporate executive to leader of a wisdom academy, Conley thinks it’s a natural outgrowth of everything he’s done. He’s always been interested in personal growth and has sat on the board of the Esalen Institute, a sort of thinking person’s retreat center in Big Sur, California, for eight years. He likes to create transformational travel experiences, and he knows the hospitality business.

For this venture, Conley didn’t have to look far for a suitable property. He chose his own beachfront home, in El Pescadero, which he converted into the main living and learning area for the academy. He bought and renovated several nearby homes, and built a few more. Famed hotel designer Oren Bronstein, with whom Conley collaborated at Joie de Vivre, designed the luxurious spaces. The campus has hot tubs, a 25-yard-long swimming pool, and a massage studio. So, yes, it’s personal and professional transformation, but with a lot of tasteful throw pillows.

Unlike the cutthroat Bay Area tech world, where Conley experienced his own repurposing, as he calls it, the academy takes a gentler, more mindful approach. There are about 16 students enrolled a week. Days start with meditation or yoga. There are long periods in which participants can write in journals and walk on the beach. A resident shaman is on staff. 

People from 14 countries have already attended the academy, or are enrolled to do so. Students include CEOs and social workers, artists and Silicon Valley lifers. 

The weeklong courses, many taught by Conley, have titles like “Consciously Curated Life” and “The Art of Transformation.” They involve group discussions on modern learning and how to stay curious, and journaling on a number of questions, including “What is my purpose and how can it be used as a magnet for collaboration?” Another prompt from the workbook: “How can I use my counsel to change the world around me?”

On Wednesdays, there’s a session called “Everything You Always Wanted to Know About Tech but Were Afraid to Ask,” in which participants can (sometimes sheepishly) ask others to show them how to use Google Docs or Slack. There are recommendations for further reading on intergenerational collaboration.

Conley teaches students to remain relevant in their professional field by staying open to learning and change. It involves embracing the beginner’s mind, the growth mindset that rewards the ability to evolve and repurpose yourself.

“There are people who believe that your potential is unlimited, that who you are is not fixed, and that you can evolve and grow.”

“Your curiosity and passion and engagement will pay off,” he says. “People will be drawn to you and see your age not as an impediment, but, in some cases, as exactly what they need.”

At $5,000 per week, the price tag to attend is steep, but scholarships are available, and Conley says that his staff is “aggressively seeking out people who can’t afford to come.”

Kari Henley, a 51-year-old from Fort Collins, Colorado, attended the academy last year, while it was still in its beta testing phase. She’s the founder of a company that helps professionals in the aging industry, in fields like caregiving and longevity research, network online. She arrived at a difficult time, personally. She was going through a divorce, moving to a new home, starting a business, and caring for her own aging mother. Henley’s stay at the academy gave her a chance to regroup. The academy uses a potent image for change, one that resonated with Henley.

“We talked a lot about this thing called liminality, being in an in-between space,” she says. “The analogy we discussed often was about being a chrysalis, that form between a caterpillar and a butterfly, when you feel like you’re goo. Gradually, the chrysalis opens up and its wings dry and it’s a new animal. But the point was to embrace this stage at midlife, when you’re in transition, and to say, ‘OK, I’m a mess right now. I’m goo.’”

By the end of the week, Henley had made important connections with other students and felt that she “had a whole other half of my life to live and design and create.” It gave her a new perspective on managing her team of employees, whose ages range from 19 to 86.

“Because of where we’re standing—in the middle—we have to commit to both directions,” she says. “We have to make friends with people 20 years older because they’re so inspiring. And we need to support those who are 20 years younger so we can continue this vibrant circle of life. It doesn’t benefit us to just hang out with people the same age as us. Because, really, that limits your perspective, doesn’t it?”

Barbara Waxman, a Bay Area–based life coach for people at “midlife and better” and a guest teacher at the academy, sums it up: “People often come in feeling that their story has been written, and they leave feeling that they can be the author of their future life.”

Though the academy was created for students in midlife, participants in their 30s have already attended—in part because irrelevancy in Silicon Valley can start as young as 35. Conley believes that every generation needs to be included for anything to change. That’s why he gives everyone an assignment when they leave the academy: Find a younger person, or people, and become a mentern, as he was at Airbnb.

Conley has taken his message on the road, becoming an activist for intergenerational collaboration in the workplace. His TED Talk on the subject garnered more than a million views. And he’s formed a small advocacy group with major players in the field—including Laura Carstensen, director of the Stanford Center on Longevity; Ken Dychtwald, founder of Age Wave; and Marc Freedman, CEO of—to try and create a movement. There’s evidence that the movement is picking up steam.

Conley has given talks at Google and LinkedIn. He spoke at Facebook recently, to a room filled with 100 human resource executives (average age: 28). His hope is that age will be considered in more diversity and inclusion programs; only 8 percent of companies do so now, Conley says. He knows an organization is made better when it’s steered by people of all ages.

“The workplace should be like an intergenerational potluck,” he says. “We need to create a compact where everybody brings what they have to the table—what they’re best at, generationally.”

Laura Hilgers is a freelance writer based in the Bay Area. Email her at [email protected].

Photography by Jason Madara

Originally Published January 2019