What Is a Midlife Retreat? A Former Airbnb Exec Wants Travelers to Try Them

Chip Conley achieved quite a lot in the first portion of his adult life. By his mid-twenties he was building a boutique hotel chain, Joie de Vivre, which he would eventually sell (it’s now part of the Hyatt group). Following that, and with several books under his belt, he became a consultant to the founders of a small startup known as Airbnb. Officially its head of global hospitality and strategy, he was known as a “modern elder” by the millennials starting to shake up homesharing.

So perhaps it’s inevitable that, as middle age inexorably snuck up on him, he turned his thoughts to the pitfalls and promise of later life, and how to tie that into his experience with travel and hospitality. Resting on laurels was never going to be on his agenda. Conley launched the Modern Elder Academy (MEA) in 2018, aiming to help people enter, as he says, a “midlife chrysalis” rather than a midlife crisis. Midlife tends to bring big life transitions, including empty nests, divorce, or career changes, but as the site suggests, it’s also a time to “inspire renewed energy and new experiences.” The MEA curriculum encourages people to consider new hobbies or revisit old passion projects.

There are online components to the MEA universe, but the heart of the academy lies in its in-person, five-night workshops, held at a beachfront campus in Baja, Mexico, and in a new-for-2024 regenerative ranch in Santa Fe, New Mexico.

An average day might begin with breakfast and meditation before a “core conversation” (featured speakers include the likes of travel writer Pico Iyer and musician Michael Franti, as well as shamans and Native elders), some yoga or art, then perhaps a sound bath. Since Conley comes from a travel background, destination-specific experiences are part of the retreat DNA, too. For instance, in Baja, there are surf lessons, and in Sante Fe, “equine-assisted learning” (psychological techniques based on how horses respond to training). And participants aren’t expected to be off the grid or the sauce. “We’re sort of for the bad boys and girls who want a little alcohol at night and also want to have access to tech,” Conley tells me.

He also insists that MEA isn’t just for people parachuting out of corporate careers. Financial aid is available, and attendees represent a mix of life experiences. “One of the best things about the program is you have a firefighter next to an elementary school teacher next to an investment banker or a CEO of a tech company,” Conley says. “That diversity of people makes it interesting. People are less inclined to compare themselves to each other.”

Photo courtesy of MEA

The retreats leave plenty of time for exploring the area, and the locations play an important part. Conley fell in love with Baja’s laid-back mix of desert and ocean when he started going there some 13 years ago. He bought a home, started writing a book, Wisdom at Work: The Making of a Modern Elder (Crown Currency, 2018), and concocted the idea of a midlife wisdom school during a run one morning. His ties to Santa Fe go even further back. “I grew up in Long Beach [in Southern California], and every summer we would drive out to Santa Fe because my uncle works for the Navajo Nation right on the border of Arizona and New Mexico. I ended up spending a lot of time here in Santa Fe, and I remember I always said to my parents, ‘Oh, I don’t have a passport. How did we get into this country?’”

Here, Conley offers more about the program and his thoughts on travel in middle age and later life.

How do you feel the travel industry does or doesn’t cater to people in their midlives and beyond?

In the two dozen years I ran Joie de Vivre and created 52 boutique hotels, I always believed that a great hotelier is a mind reader and imagines what a guest needs that might not be obvious. Our job is not to just meet the expectations and desires of our guests, but it’s to deliver on their unrecognized needs as well (I wrote about this in my book Peak: How Great Companies Get Their Mojo from Maslow (John Wiley & Sons, 2007). For those in midlife, the unrecognized need is to add a sprinkling of external adventure and internal self-discovery. I believe that “transformational travel” (when a guest sees their vacation as a transformational experience) is a growing trend across all age ranges, but especially those in midlife.

Are there travel experiences or destinations that are better when you’re in your midlife and beyond?

Our guest faculty member Pico Iyer says, “We travel, initially, to lose ourselves; and we then travel to find ourselves.” It’s less about the destination and more about what will “move” you, break you out of your normal routine. By midlife, we’ve often become a bit habitual, so whether it’s going to Burning Man, doing a foreign-language immersion halfway around the world, or coming to a midlife wisdom school workshop at MEA, your travel is meant to open your eyes and your heart to new experiences and prime your sense of curiosity.

Photo courtesy of MEA

Can you tell me a bit more about MEA’s origin story?

I started MEA because I saw so many of my friends in their forties, fifties, and sixties a bit bewildered or stuck in midlife (if you’re 54—the average age of our alums—and you’re going to live till 90, you are only halfway through your adult life if you start counting at 18). Based upon my past two decades, I found that my late forties were treacherous and my fifties were my favorite decade, and the U-curve social science research bears that out. Yale’s Becca Levy [a professor of social and behavioral sciences] has shown that when you shift your mindset on aging from a negative to a positive, you gain seven-and-a-half years of additional life, so—in many ways—we’re a living laboratory for Becca’s work.

We have three pillars in our MEA program: navigating transitions, cultivating purpose, and exploring and owning your wisdom. The five-day residential workshop at our two campuses in Baja and Santa Fe is very experiential, and nature is a teacher for certain parts of the program. We’re proud that we now have 5,000+ alums from 48 countries and 28 regional chapters.

Who attends these conferences?

We have workshops year-round in both Baja and Santa Fe, with the typical workshop being about two dozen socioeconomically diverse people. Many people are in the midst of professional, personal, or spiritual transitions and are seeking a community of others they can learn from, as MEA believes that “wisdom is not taught, it’s shared.” Once you graduate, your workshop cohort stays in touch for months and years to come with regular Zoom calls and reunions.

Have any guests made big life changes following a retreat?

There are so many life-changing stories. We often say that the four shortcut paths to purpose often come from something that excites you, agitates you, makes you curious, or something passionate from earlier in your life that feels neglected. We had a 60-year-old litigation attorney who hated what her job did to her emotionally but had no idea how to shift out of it. At our Baja beachfront campus, she started having dreams of walking on the beach with her deceased grandmother and then started dreaming about cooking pies with her (which she loved doing as a teenager). By the end of the week, she realized she wanted to test out pastry chef school, and ultimately, she opened a bakery in her neighborhood and is so much happier. We’ve had people meet in a workshop and start a business together or fall in love and get married or realize that it’s time to reconnect with a long-lost friend or family member.

What’s your take on the newish trend of “longevity travel”?

With an aging population and much of the discretionary income being in those who are 50+, I see “longevity travel” as being a long-term trend. For many, that may mean going to a biohacking resort where you experience stem-cell regeneration or cryotherapy, the physical science of longevity. At MEA, we believe in “long life learning,” how to live a life that’s as deep and meaningful as it is long, so our program is more focused on the socio-psychological science of longevity. I believe that midlife wisdom schools, dedicated to helping people reimagine and repurpose their lives, are going to be like Canyon Ranch was to the spa industry 50 years ago.

How do you use your own vacation time?

I love a place that allows me to connect with my mind, body, and spirit. A great vacation would have a little bit of education, some exercise and healing bodywork, and an introduction to a soul healer. So, I love Bali, Peru, Austria. love the lakes, hikes, and outdoor culture in Austria during the summer and am a fan of the medical spa, Mayrlife. I’m also a hot springs junkie, so my next trip is to Iceland.