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BookWatch: Midlife can be ‘dark and gooey,’ says Chip Conley. How to embrace it anyway.

As creator of the world’s first “midlife wisdom school,” Chip Conley wants to reinvent how people perceive midlife: not as a crisis, but as a chrysalis. 

It’s a transformative stage — with a dark and gooey inside — that is crucial to end one era and begin a new one. 

Conley knows a bit about changing and transitions.

He was the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then later became Airbnb’s head of global hospitality and strategy. At Airbnb he became a mentor or a “modern elder” to the younger founders.

He then founded MEA, the Modern Elder Academy, which seeks to help and support adults through transitions in their midlife years, with a particular emphasis on those aged 40 and above. The first campus, in Baja California Sur, in Mexico, opened in 2018 and a second campus will open early next year on a 2,600-acre regenerative horse ranch in Santa Fe, N.M.

MEA combines teachings from modern science, as well as philosophers, writers, poets and yogis, and then melds them into lessons for individuals looking for growth and guidance as they navigate midlife, Conley said.

In Conley’s latest book, “Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age,” he tackles this era of midlife and its lessons. The book is to be released on Jan. 16.

The former longtime lodging executive Chip Conley co-founded the Modern Elder Academy in 2018.


MarketWatch: This is your seventh book. How did it come about and what did you feel you needed to say? 

Conley:  I have not written a book since I created the MEA. I also lost five friends to suicide and had my own dark night. But my 50s were my favorite decade. I began doing research on midlife and read Becca Levy’s research about how your attitudes on aging can increase longevity and help you gain seven years of life. I had a growing curiosity on longevity and health span but there was nothing out there about psychological and emotional changes people go through. I thought I could help get out there this idea of “Hey, there’s an upside to aging. Yes, some things get worse but some things get better.” 

MarketWatch: If you had had this book as a tool when you were younger, would you have done things differently?

Conley: Yeah, I would do things differently. Gen Z and millennials are good examples of generations doing things differently. It’s important to have self reflection in your early 20s to make sure you’re not jumping on a treadmill someone else created for you. You have to consciously create your life. The reason for a midlife crisis often is that people look at their lives and say I need to change something. Midlife is full of transitions. There are a lot of transitions, but not a lot of support.

MarketWatch: You suffered a near-death health scare and had cancer. Do people need that kind of major upheaval to gain perspective?

Conley: Often when there’s involuntary transitions, people sit up and take notice. When people are comfortable, they are less likely to change. At the Modern Elder Academy, we’ve had 4,000 people from 45 countries come through. Many come with the recognition of a need to change. There’s a feeling as if the way they’ve been living isn’t working for them. 

MarketWatch: Can you talk about the midlife branding crisis?

Conley: We need to rebrand what midlife is. It’s a chrysalis. There’s a younger stage, and there’s a dark and gooey era, and on the other side of that is something very beautiful. You may need to go through a transitional part. If people do not take active steps towards reconsidering the second half of life, circumstances may force them to. 

MarketWatch: Not everyone has the time, money or resources to go back to school or reinvent their life. Is this introspection and change a luxury or is it accessible to everyone?

Conley: People can do it at whatever speed they want and at whatever price. Buy a book. Read a blog — read my daily blog for free, called “Wisdom Well.” Join a support group. Create a book club. Take an online course. There’s financial aid for MEA and for $500 you get a five-day experience. I lost friends to suicide. I don’t want to say they couldn’t have access to help.

MarketWatch: You mentioned that your 50s were your favorite decade. Why?

Conley: I felt relieved. I stepped away from a relationship and a company I no longer wanted to work for. I had some health stuff. Your 40s, often you’re trying to hold on to your youth, and you’re full of regrets. In my 50s, you start to wonder what you have to offer. I could feel like an old dinosaur, but I didn’t. I got healthy. I edited the thing from my life that didn’t work. 

MarketWatch: We see the Rolling Stones going back on tour in their 80s, Martha Stewart in the Sports Illustrated swimsuit edition — are they outliers of older adults, or is that what we can expect to see as people live longer?

Conley: Half of the kids born today are going to live to their 100s. A 100-year-old life is much more available in many parts of the world today. The U.S. has its own longevity crisis right now. But more and more people are living longer. The notion of life being split into three parts — you learn, you earn and then you retire to die — doesn’t make sense. You can go back and get a master’s, get a college degree. Take a sabbatical. You don’t need a midlife pitfall, but there needs to be something to change the habits. Take a weekend every season that’s devoted to personal growth and really focus on new practices. It’s all about people taking action steps.

MarketWatch: Often when people retire or give up a career or job that defines them, they panic. Do you have any advice for them? 

Conley: Any transition is messy. It’s the end of something. Then, it’s the messy middle and then the beginning of something new. When you’re ending a career or job you’ve been at for a long time, you should think of how to celebrate that — that an era is over. It’s not the gold watch at retirement. They don’t do that anymore. But ritualize something. People often do a bad job of saying that era is over. And the messy middle is hard — it feels like the ground is moving under them. You have to see through the through line — what takes you to the next step. The third stage, the butterfly tries to fly and its wings are wet and it often ends on the ground. The key is to not be critical of yourself. People can really lose their sense of self-confidence.

MarketWatch: You talk in the book about midlife being freeing because you have no more F’s left to give. Why is that an important step?

Conley: Not worrying what other people think of us, or caring about what others said, or that my ego doesn’t need a thing. It’s not giving a F — like a cranky man who doesn’t care about anything. It’s about saying no to things so that you can have more opportunities to say yes to the things that matter to you. You let go of the extras.

MarketWatch: You reference the movie “American Beauty” a few times in the book. Why did that movie resonate with you?

Conley: Kevin Spacey’s character seems so unhappy and nihilistic. He gets the red sports car and is flirty with his daughter’s best friend. It’s very much how people think of midlife people. But that’s not the only way to do it. 

Editor’s note: This interview was edited for length and clarity.

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