From Crisis to Chrysalis: Rethinking Retirement with Chip Conley

See All Posts

6 minute read time.

“This isn’t a midlife crisis—it’s a chrysalis. It may be dark and gooey, but it’s where the magic happens.” — Chip Conley

Chip Conley calls himself a “social alchemist.” Or in other words, “a mixologist of people” who knows how to bring out the best in them. In his mid-20s, he was a commercial real estate developer craving a more creative career. He went on to found Joie de Vivre Hospitality, which became the second-largest operator of boutique hotels in the U.S., and later joined Airbnb as Head of Global Hospitality and Strategy.

It was there that he stepped into the role of “in-house mentor” to the company’s three young founders, earning the nickname “Modern Elder.” “They said a Modern Elder is someone who’s as curious as they are wise,” shares Conley. “When they first called me the Modern Elder, I was like, I don’t know about that, but then they said it was the alchemy of curiosity and wisdom. And I liked that.”

In 2018, Conley spun that title into something bigger: The Modern Elder Academy (MEA), a midlife wisdom school with over 7,000 graduates from 60 countries and 56 regional chapters. “Part of what we’re doing is building a movement and listening to people in midlife and later about what their needs are, because this is a whole new era of longevity,” he says. 

Chip Conley, Founder and Executive Chairman at MEA, NYT Best-Selling Author, Speaker

MEET THE “MODERN ELDERS”

According to Conley, MEA attracts people in their 50s, 60s and 70s, who aren’t quite ready to retire, but are ready for what’s next. For many, that next begins with a “pit stop” where they can refuel and reimagine their purpose.

Conley says this chapter isn’t a midlife crisis, but instead a chrysalis. “In that chrysalis, or cocoon, it’s usually dark and gooey and solitary, but it’s also where the magic happens,” he says. And, the data agrees. The U-curve of happiness shows that while life satisfaction dips in midlife, it rises steadily in later years. “Around midlife, you’re moving into an era that’s got a different set of rules, and therefore, there are things you need to let go of,” he says. “The first half of your life, you’re accumulating. The second half of your life, you’re editing.”

WHAT WE’RE GETTING WRONG ABOUT LONGEVITY (AND WHY IT’S COSTING US)

Conley’s favorite question to ask at the MEA is, “Do you know what percentage of your adult life is still ahead of you?” Most people get it wrong, underestimating just how much life they have left.

That’s partly because, as Conley explains, the U.S. has poor longevity literacy. We base our expectations on outdated life expectancy numbers and don’t focus enough on more optimistic odds that come with reaching certain ages. For example, the average man in the U.S. lives to 75.8 years. But, if you make it to age 65, odds are you’ll live until at least 82.

The consequences of not fully understanding longevity are big, causing some to under save for retirement, or assume they’re “too old” to try something new, like learning a new skill or starting a new business. “10 years from now, what will you regret if you don’t learn it or do it now?” Conley asks his MEA students. “That’s a really valuable question. Anticipated regret of something you’re going to regret 10 years from now is like a form of wisdom.”

GOING TO RELATIONSHIP COUNSELING…WITH YOUR MONEY

At MEA, Conley invites students to look at their relationship with money the same way they’d approach a romantic partnership. “What would money say about you? And what would you say about money, and what’s that relationship like? And how could you improve on that relationship?” he asks.

For many, the first step in building a better relationship with their finances is evaluating their “money script,” in other words, the beliefs they hold about money. Then comes a two-sided audit: How are you earning, and how are you spending?

On the spending side, Conley says that some of his students discover they can live well for less (and in some cases, significantly less) by living abroad. “We get so many people who come to our campus [in Mexico] and say, ‘Oh, wow, I had never thought that I could actually live overseas for one-third the cost of what it would cost for me to live in the United States,’” he shares. “There are options [Costa Rica, Portugal, Mexico] people moving to all kinds of places. That’s a whole different framework from our parents.”

On the earning side, Conley argues that we need to rethink retirement entirely. “Our historical point of view on retirement probably needs to be retired,” he says. “One of our messages is, you don’t just need to say ‘I’m retiring, I’m going to sit on the couch and eat bonbons and watch 47 hours of TV a week,” he says. “Instead, you can do a little bit of that and get clear on your purpose. But most importantly, you can realize that you can be earning money for the rest of your life.”

Conley says some of the more common ways older people continue to earn money are through passive income streams, such as rental properties, or part-time pursuits that bring them joy, like coaching.

THE MIDLIFE MUST-DO LIST

Out of the thousands of students MEA has welcomed, Conley says most are focused on improving three areas of their lives:

  • Nurturing relationships: Whether it’s spending more time with their parents, reconnecting with their partner, or building a more robust social life, Conley says midlifers are prioritizing their relationships and realizing it’s now or never.
  • Learning something new: “Learning a skill that you’ve been sort of holding off on, whether it’s learning Spanish, learning to surf, learning guitar or learning AI, there are a lot of things that people [say they’ll regret if they don’t do],” shares Conley.
  • Living somewhere different: “I think travel is not enough,” says Conley. “The thing that people say is that they would like to live in a different place, and usually, in a foreign country,” he says.

At the end of the day, Conley says the evolution we go through as we get older is a lot like a teenager “growing into new shoes all the time.” However, in midlife, the shift is much more profound. “It [getting older] is a form of saying ‘these shoes are too small for me,” he shares. “In midlife, we’re outgrowing roles, not shoes.”

RELATED CONTENT:

Related Articles

Stay informed with the latest updates on protected income planning.