vague borders of midlife are thought to start around 45, the age when Chip Conley’s world began falling apart. With the burst of the dot-com bubble in 2000, the Bay Area hotel chain he’d founded nearly folded and, not long after he’d revived it, the hemorrhaging resumed with the economic crash of 2008. During that same period, his eight-year relationship ended, his foster son was wrongly imprisoned for months until the verdict was overturned, and five of his friends committed suicide. Though his closest advisers urged him to keep his business going, his heart was no longer in it. “What had been a calling had worn off and was just a job, not even a career,” Conley recalls. He sold his life’s work at the bottom of the market. To make matters worse, he also died—literally, as some millennials like to say.

Some millennials also say, “OK Boomer,” an expression of frustration used when an older person—usually one of the 73 million baby boomers, like Conley—seems out of touch. For many of the 168 million Americans born between the early 1980s and mid-2010s, the term also expresses a sense that boomers have made decisions that damaged the prospects for future generations. And yet if a story could make people rethink intergenerational relations and aging itself, it is Chip Conley’s—not because he flatlined, but because of what he did afterward.

But first, his death: During a baseball game at a friend’s bachelor party, Conley cut his leg sliding into third. The wound became infected, and a few days later, before giving a talk in St. Louis, Conley took antibiotics. He had an allergic reaction and his heart stopped. Paramedics resuscitated him several times before he finally stabilized.

Experiencing so much distress and seeing so many negative portrayals of midlife made Conley question whether he still had something to contribute. What he’d thought was his life calling had lasted nearly 2½ decades: the chain of 52 boutique hotels he began creating at 26, buying rundown hotels and reinventing each one according to a theme—luxury camping, new age wellness or romance novels. But with so many years ahead of him, he wanted a fresh calling. During his search for it, he accepted a job as Head of Global Hospitality and Strategy at Airbnb, the iconic millennial online marketplace for home rentals. There, among colleagues who were half his age and far more fluent in tech, he contemplated his role as an elder and, in the process, joined his ideas to those of a group of thinkers trying to reimagine aging—looking for answers to how societies can adapt as life spans increase, how generations can work together, and how individuals can use additional years to return to school, switch careers and renew their sense of purpose.

As it turns out, to start over, dying wasn’t required; you didn’t even have to be very old.

In many ways, Conley came of middle age on the cusp of an identity crisis for boomers—the result of converging tectonic forces: the tech revolution that favors skill sets overwhelmingly possessed by young workers and the increase in longevity that has resulted in a rapidly aging populace. Accelerating this collision is automation, which displaces an aging workforce and increases the demand for workers with coding skills.

Conley lays out the situation in his latest book, Wisdom@Work: The Making of a Modern Elder: “More than half of American baby boomers plan to work past the age of 65 or not retire at all, and the number of workers in the 65 and older demographic is expected to increase at a faster rate than any other age groups. In 2025, we will likely have three times as many 65-year-olds working in this country than we did 30 years earlier, and the number of workers age 75 and older is expected to increase by an unprecedented 6.4 percent annually through 2024.”

Though financially stable, Conley felt daunted as he faced a culture transformed by tech, dominated by youths and pervaded with ageism—a prejudice he himself shared, he realized after accepting the job at Airbnb in 2013. The company’s founders had read his 2007 book, Peak: How Great Companies Get Their Mojo from Maslow, in which he describes managing his hotels based on psychologist Abraham Maslow’s hierarchy of needs to ensure that every employee was happy and engaged. “They wanted to create a culture at Airbnb that was comparable,” Conley recalls. “So I joined and realized I was twice the age of the average person there and I’d never worked in tech before.” At 52, he understood neither tech culture nor the millennial argot of his co-workers. Music and pop culture references went over his head, and he was startled to hear women call each other “dude.” When others discussed “shipping a feature” (releasing a product that may need alterations and could be endlessly refined), he was lost. “I felt like maybe the business world, especially the technology part of it, had passed me by and there was no way to catch up.”

On a spring day, he met his father, a 75-year-old retired banker turned real estate investor, for a hike above Los Altos Hills. When Conley lamented feeling like “the old fogey at Airbnb,” his father said, “All I’m hearing are your fears. How can you turn your fear into curiosity?” Conley was surprised to realize he’d assumed he couldn’t learn tech lingo and had nothing to offer. “I made the shift,” he says, “to realizing how, instead of being focused on my self-absorbed fear, I could serve and be helpful to these young people and their mission for the company.”

At Airbnb, Conley increasingly thought about a new generational compact in which old and young learn from each other. “I realized I could offer some mentoring,” he says, “while also learning and in essence being mentored by them.” Recalling Conley’s time with Airbnb, CEO Brian Chesky, in the foreword of Wisdom@Work, writes: “He affirmed that we all have a story to share and something to learn from one another. That if we take the time to connect, we can learn anywhere and from anyone. . . . He’ll show you that wisdom has very little to do with age and everything to do with approach.”

Conley’s reflections at Airbnb led both to Wisdom@Work, in which he describes making peace with being an elder, and to the Modern Elder Academy (MEA), the school he founded in Baja California Sur in 2018 to help “people navigate midlife,” according to its website—which also notes that “a positive perspective on aging can add 7.5 years to our lives.” Through group projects, the academy’s weeklong workshops teach people that they can learn at any age.

After 20 years in the shrinking field of publishing, Irene Edwards, former editor in chief at Sunset magazine, says attending MEA “made me open to completely new experiences.” She subsequently sold her Bay Area home and moved her family to Denmark to work in interaction design—a field exploring digital environments and interactive technology such as mixed reality and artificial intelligence. “It’s basically designing the experience of the user,” Edwards explains. “It’s really cutting edge. If you told me that I was going to be working in this field a year ago, I would have laughed.”

Similarly, Joseph Del Hierro, ’83, a film producer formerly with Disney ABC and Walden Media, attended MEA because he found himself sidelined in the youth-obsessed film industry and wanted to do nonprofit work. (He now raises funds and fosters mentorship networks for an organization that helps underprivileged students apply to college.) “You learn that you’re just at the beginning of your new cycle,” he says. “Social media comes down on people of my age group, but we have a lot to offer.” Listening to Conley talk about his own struggle to hear “elder” not as “elderly”—someone in the last years of life—but as a person who is simply older than others and has many years left, Del Hierro revised his own ideas about aging.

“When I was 57,” Conley recalls, “I’d taken some longevity tests that said I would probably live till 98. If I do, I wouldn’t have been even halfway through my adult life. The question I started asking myself was what is it that I wish I’d learned 10 years ago and what are the things I should learn now, so I don’t regret 10 years from now that I didn’t learn it now?”

Perceptions of life stages shift as cultures change. In 1960, French historian Philippe Ariès proposed that “in medieval society, the idea of childhood did not exist,” arguing that children were treated like small adults until, after centuries of social and economic transformation, childhood became a concept in 17th-century family life. Similarly, in 1904, G. Stanley Hall, president of the American Psychological Association, argued that adolescence was becoming a developmental phase thanks to universal education and child labor laws that freed the teenage years of the burdens of adulthood.

More recently, the term middlescence has begun circulating in English, referring to the period of self-doubt and readjustment in midlife. Conley argues that, like adolescence, middlescence should be shaped by education. “If adolescence is the transitional period between childhood and adulthood,” he says, “middlescence is the transitional period between adulthood and elderhood. It is similarly a period when you go through emotional and hormonal changes. But it’s a period where we have zero in the way of schools or tools for people to understand this next period of their life.”

It is precisely this challenge—creating educational opportunities for people later in life—that inspires Phil Pizzo, founding director of Stanford’s Distinguished Careers Institute. Born in 1944 in the Bronx and raised in Queens, Pizzo grew up in a family of Sicilian immigrants that imbued him with the value of education. His mother, a homemaker, didn’t finish high school, and his father stopped in sixth grade; after returning from World War II, he sold women’s coats during the day and spent nights as a cashier at Yonkers Raceway. Pizzo became the first in his family to attend college. After earning his MD, he began a residency at Children’s Hospital Boston, where he had the experience that first made him think about midlife education, though he was only in his 20s.

“I saw incredible people who had invented the fields of pediatric surgery or oncology,” he recalls. “They were more senior people [by then] and were not at the top of their game and were not being treated with the same degree of respect. I found that pretty distressing. I made the decision that I needed to have an alternative career plan so that when I got to that point, I wouldn’t be hanging on.”

Over the following decades, Pizzo served in many roles—leadership positions at the National Cancer Institute, physician-in-chief of Children’s Hospital Boston, chair of pediatrics at Harvard Medical School and dean of the Stanford School of Medicine—but he was also laying the groundwork to retire and do a PhD in history. A long-distance runner, he listened to history books first on a Walkman, carrying multiple cassettes for long runs, then on an iPod and finally on an iPhone. But as 2012 neared—the date he had set for stepping down—he began to question his plan. “That’s when I realized that the social narrative that had guided most careers up until then—you get educated, you work and you retire—was less relevant,” he recalls.

Pizzo found himself thinking about American life expectancy’s increase from 46 years in 1895—when Herbert Hoover graduated from Stanford’s first class—to 79 today. Mindful of the challenges facing aging Americans, he focused back on education, founding the Distinguished Careers Institute, a program that allows people in midlife to attend Stanford for a year.

“It turns out that in healthy longevity, education is one of the single most important determinants,” Pizzo says. “People who’ve had less than a high school education do not do as well compared to those who do. Those who’ve had greater than a high school education have a much more significant likelihood of doing well.”

Likewise, studies show that community interaction increases longevity, while other research has warned of epidemic levels of loneliness—with 47 percent of Americans describing a lack of meaningful relationships. Social isolation, whether from changes in the labor market, economic hardship or other factors, often correlates with drug overdose, suicide and alcohol-related illnesses—the “diseases of despair” responsible for the decrease in life expectancy since 2015.

If this crisis has a solution, it might be in a return to education, says Dianne Millner, who retired from a law career supervising the real estate and economic development units of the Oakland City Attorney’s Office to be a 2018 DCI fellow. At 68, she studied education so she could provide legal and strategic advice to an educational nonprofit. DCI’s impact on her life was “monumental,” she says. “One of the biggest factors was forming a new cohort.”

DCI accepts approximately 40 fellows (including their partners) each year, during which they audit classes and meet frequently to discuss their experiences and goals. Since the challenge of making lasting friendships later in life is often contrasted with the ease of establishing them in college, returning to school at any age offers the possibility of building community while renewing one’s purpose.

If Pizzo’s fears about aging haven’t borne out, it may be precisely because of purpose: his new mission with DCI. “People in their 50s who have a high correlation on the scales of purpose,” he says, “have a significant improvement in all-cause survival.” In recent years, programs similar to DCI have started up at the University of Texas at Austin and the University of Notre Dame. Though Pizzo envisions a future in which freshmen enter university with classes of midlifers, such programs are expensive. Furthermore, DCI has limited space, and only 217 people have participated since the program’s 2015 launch. However, they, like graduates of MEA, have gone on to be ambassadors for lifelong learning, and Pizzo sees the program as a prototype. Making the model scalable—capable of supporting the educational needs of millions—remains the challenge.

Aging is a field that Laura Carstensen, professor of psychology and founding director of the Stanford Center on Longevity, likes to say she came to by accident. “I was in a car accident when I was 21 years old that landed me on an orthopedic ward with 20-plus broken bones for four months.”

While she was on her back, with one leg in traction, the nurses gave her the job of keeping elderly patients upbeat. Her conversations with women changed her views on aging, making her realize that older people aren’t all similar. “I got to see the diversity in their circumstances, attitudes, roles, statuses and places in life,” she says. Simultaneously, she also saw how similar her experience—confined to a bed, requiring help—was to theirs.
“I began to wonder how much of aging is a biological process—and it clearly is a biological process—but how much of that process was being shaped by the social world.”

Until then, Carstensen had shrugged off college despite the hopes of her father, a biophysics professor at the University of Rochester. “It was the ’70s,” she says. “That’s my only excuse.” But during her convalescence, he offered to tape course lectures. “I picked psychology, and that man went to every single introductory psychology class, and I took my first college course in the hospital, surrounded by old women.”

Over the following decades of research, Carstensen concluded that writing on aging was often reductive and there was little evidence for theories about fixed, biologically determined stages that all people go through. “Part of the problem with stages,” she says, “is that we’re keeping everything up to 60 the same and then saying it’s at 60 that we’ve got more time.”

In her 2011 book, A Long Bright Future: Happiness, Health, and Financial Security in an Age of Increased Longevity, she points out that in 2050, there will be a million centenarians in the United States, compared with 80,000 today. With such extended life spans, Carstensen argues, tacking extra decades to the end makes less sense than casting off notions of stages and spreading the extra years throughout our lives. “We wouldn’t be deluged with too much work, which is what we do now in the middle, or too much education, which is what we do early, or too much leisure at the end.”

Carstensen believes we should integrate leisure, education and work from the beginning. “Let’s make high school six years instead of four,” she says, “and one of those years you volunteer in your community and the other year you work. If you think you might want to be a physician, you work in a hospital.” The result would be healthier, more balanced youths who have a clearer sense of purpose and who learn to create financial security for longer lives.

Such an integration of education and work would also create less age segregation—a problem to which “OK Boomer” could be attributed. Young people working with adults and adults studying with the young could foster understanding. Just as Carstensen adjusted her views on aging as she became friends with older women, Kate Jerome, a children’s book author, publishing executive and 2015 DCI fellow, grasped the frustrations of young people better after having taken classes alongside them. “Opening conversations between generations,” she says, “can only help get rid of stereotypes.”

As for “OK Boomer,” Carstensen sees the conflict behind it from multiple angles. “I don’t want people to judge me based on my age,” she says, “but we really do need to think about what our responsibilities are to other generations.” In her writing on the importance of older generations actively investing in young people, she quotes a Greek proverb: “A society grows great when old men plant trees in whose shade they know they shall never sit.”

Though the United States has a long history of adult education—from the Lyceum Movement in the 1800s and Chautauqua assemblies at the turn of the 20th century, to the massive open online courses offered by learning platforms and universities—few existing programs provide community and funding or are tailored to contemporary challenges.

Transforming higher education, Chip Conley believes, may require a government initiative similar to the G.I. Bill, which bankrolled education for veterans after World War II. One opportunity for such an intervention, he argues, lies in the educational crisis predicted by Clayton Christiansen, the Harvard Business School professor who coined the term “disruptive innovation.” In 2018, Christiansen stated that 50 percent of colleges would close over the next decade since their standardized approach was irrelevant in the marketplace. Though critics say his prediction is exaggerated, a number of colleges have shut down in recent years or are struggling financially, and the COVID-19 pandemic could be the final blow to many.

“There are a lot of campuses around the United States that focus their energy on 18- to 22-year-olds, and many of those campuses are not going to make it,” Conley argues, pointing out the obvious opportunity to integrate education for people of all ages and shift the focus to lifelong learning—an experience so in demand that Conley was surprised after starting his academy. “We thought we wouldn’t accept anybody other than people 45 to 65, but almost 25 percent of the people have been younger than 45 or older than 65.”

While boomers might be bellwethers in the social experiment with second acts, the indications are clear that the results will apply to the following generations and that more and more people in those generations know it. Automation and changes in the job market are likely to accelerate in lockstep with the ever-shortening half-life of knowledge, and job loss has become more dire since the emergence of COVID-19. If anything, the pandemic has highlighted the vulnerability of workers and institutions and the degree to which career change is often not a self-actualizing choice but a survival imperative. With the ensuing financial crisis, many more people will likely need new jobs, and those jobs will have to last longer to compensate for diminished retirement portfolios. Increasingly, the future suggests that the new normal for all generations will be adaptability in the face of uncertainty. To this end, developing flexible social structures and educational systems is crucial.

Recalling when she first began voicing the need to revise how society approaches work, education, retirement and aging itself, Carstensen says, “People sometimes said, ‘Oh yeah, how could that ever work?’ And what I say is, ‘How can this work right now? What we have right now doesn’t work. It’s not working for anybody. So we’ve got to start making some changes.’ ”