Best-Selling Author Chip Conley on Learning to Love Midlife
On this episode of Redefining Work, I’m joined by entrepreneur, hotelier and New York Times best-selling author Chip Conley to discuss the topic of his most recent book, “Learning to Love Midlife.” Chip has lots of entrepreneurial experience in hospitality, having founded his own boutique hotel line in the 1980s when he was 26, which he scaled and sold to Hyatt.
As a big name in the hospitality industry, the founders of Airbnb approached him in the company’s infancy. “They were a small tech startup that was ready to disrupt the hospitality business,” Chip says. “And they asked if I could join them as their in-house mentor and help them to take a tech startup and turn it into a hospitality brand.”
The Airbnb team members began referring to Chip as a “modern elder” — a term he initially perceived as a jab but came to appreciate over time. His younger colleagues described him as “someone who's as curious as they are wise,” he says. That shift in how he perceived midlife prompted Chip to look deeper into this stage of life, sparking two books, three TEDx Talks and the Modern Elder Academy (MEA).
Find out how Chip thrives in his midlife and how you can help your workforce and organization embrace the unique benefits and opportunities offered during this stage of life.
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Forget Everything You Thought You Knew About Aging
Culturally, we perceive midlife as a time of confusion and crisis — in large part because it’s simply not well-defined. “Midlife is a complicated life stage,” Chip says. “It is one that doesn't really have exact borders or boundaries.”
That fuzziness colors how we think about midlife, which all too often is spent mourning lost youth. “We know, famously, midlife crisis,” Chip says, but he’s on a mission to reframe how we think about this stage: “I now call it the midlife chrysalis because it's actually a time where there can be some serious transformation.”
Chip’s role at Airbnb led him to explore the dynamics of aging in the workforce, especially as older employees increasingly report to younger and younger bosses. From his personal experience simultaneously reporting to and mentoring Airbnb’s CEO, who is 21 years his junior, Chip discovered the important role people in midlife play as a “bridge between younger and older people in the workplace,” he says.
Harness Wisdom in the Workplace
Negative stigmas around aging come down to skewed perceptions. “The process of aging is perceived as a negative,” he says. “The process of growing is not perceived as negative.” Those stereotypes hold us back from harnessing the wisdom people have grown over the years, which presents a powerful opportunity for organizations.
Chip is a strong advocate for age-diverse teams. Young brains, he says, “tend to be fast and focused,” while older brains “tend to be slower but more synthetic and able to see the future and think more systemically.” Pairing these qualities on a team adds remarkable value in the workplace.
Chip shares some of the programs he’s found to be successful in harnessing the wisdom of workers in midlife, such as mutual mentorship between young and old employees. Chip served as a monitor at Airbnb, but the benefits flowed both ways. “I learned as much from them as they did from me,” he says. Chip suggests using surveys to ask who people go to for advice within the company to create a “wisdom heat map” across the organization.
Unlock Personal Growth — at Any Age
Because negative perceptions of midlife are so ingrained in our culture, HR leaders may find it challenging to help employees see the potential left in their careers. “We have more life ahead of us than we think,” Chip says.
People can help others identify and begin working toward new goals instead of giving up on new experiences. "What is it that you know now, or you’ve done now, that you wish you’d known or done 10 years ago?” Chip suggests asking. From there, he says, “the more important question is, ‘Ten years from now, what will you regret if you don’t learn it or do it now?’"
Seeking these insights and articulating new interests aids personal growth and helps transform how we view our potential in life's later chapters.
“That's part of the work we do at MEA,” he says. “We help create a crucible for people to have life-changing conversations that not just reframe their relationship with aging but actually repurpose themselves in a new way.”
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