What Is a Midlife Retreat? A Former Airbnb Executive Invites Travelers to Explore Them

By his mid-twenties, Chip Conley was already making waves in the hospitality industry, creating the boutique hotel chain Joie de Vivre, which he eventually sold to become part of the Hyatt family. With several bestselling books and a role as a consultant for Airbnb under his belt, he served as the company’s head of global hospitality and strategy, earning the title of 'modern elder' among the millennial innovators.

As middle age approached, Conley naturally began to reflect on the challenges and opportunities of later life, seeking to integrate this with his travel and hospitality insights. He rejected complacency, launching the Modern Elder Academy (MEA) in 2018. His goal? To help individuals transition into what he calls a 'midlife chrysalis' rather than facing a midlife crisis. This phase often brings significant life changes, such as empty nests, divorce, or career shifts, but the MEA emphasizes renewing energy and pursuing new adventures. The curriculum inspires participants to explore new hobbies or reignite past passions.

While the MEA offers online resources, its essence is found in immersive, five-night workshops hosted at a stunning beachfront campus in Baja, Mexico, and a new regenerative ranch in Santa Fe, New Mexico, set to open in 2024.

A typical day might kick off with breakfast and meditation, followed by a 'core conversation' featuring speakers like travel writer Pico Iyer and musician Michael Franti, alongside shamans and Native elders. Participants can enjoy yoga or art sessions and perhaps a sound bath. With Conley’s travel expertise, location-specific activities are integral to the retreats. In Baja, there are surf lessons, while Santa Fe offers 'equine-assisted learning'—psychological techniques informed by how horses respond to training. Plus, guests are free to enjoy a little nightlife and stay connected to tech. 'We cater to the rebels who appreciate a drink at night while still wanting a meaningful experience,' Conley shares.

Conley emphasizes that MEA isn't solely for those leaving corporate roles. Financial assistance is available, attracting a diverse mix of participants. 'One of the most rewarding aspects of the program is seeing a firefighter sitting next to an elementary school teacher, an investment banker, or a tech CEO,' he explains. 'This diversity enriches the experience and reduces the tendency for comparison among attendees.'

The retreats allow ample time for local exploration, with the locations adding significant value. Conley first fell for Baja’s unique blend of desert and ocean during his visits over a decade ago. He purchased a home, began writing his book, Wisdom at Work: The Making of a Modern Elder (Crown Currency, 2018), and envisioned the midlife wisdom school concept during a morning jog. His connection to Santa Fe is even deeper; 'I grew up in Long Beach, California, and every summer we would journey to Santa Fe because my uncle worked with the Navajo Nation near the Arizona-New Mexico border. I spent so much time here that I often joked with my parents, asking, “How did we get into this country without a passport?”'

In this section, Conley shares insights about the program and his perspectives on travel during middle age and beyond.

How well does the travel industry accommodate individuals in midlife and beyond?

During my twenty-plus years managing Joie de Vivre and establishing 52 boutique hotels, I always felt that a great hotelier should anticipate guests' needs beyond the obvious. Our role extends beyond simply fulfilling their expectations; we aim to address their unexpressed desires as well (I elaborated on this in my book Peak: How Great Companies Get Their Mojo from Maslow (John Wiley & Sons, 2007). For those in midlife, there's a growing desire for both external adventure and internal exploration. I believe 'transformational travel'—when a vacation becomes a transformative experience—is increasingly appealing to all age groups, especially those in midlife.

Are there travel opportunities or locations that are particularly enriching during midlife and beyond?

Pico Iyer, one of our guest faculty members, states, 'We initially travel to lose ourselves; ultimately, we travel to rediscover ourselves.' It's less about the destination and more about what will truly move you and disrupt your usual routine. By midlife, we can fall into predictable patterns, so whether it’s attending Burning Man, immersing yourself in a foreign language abroad, or participating in a midlife wisdom school workshop at MEA, your travels should inspire and expand your horizons, reigniting your sense of wonder.

Could you share the story behind the founding of MEA?

I launched MEA after observing many friends in their forties, fifties, and sixties feeling confused or stuck in midlife. If you're 54—the average age of our alumni—and you plan to live until 90, you're only halfway through adulthood if you start counting from 18. Based on my experiences, I found my late forties quite challenging, while my fifties turned out to be my favorite decade. This aligns with the U-curve social science research. Yale’s Becca Levy, a professor of social and behavioral sciences, has demonstrated that changing your perception of aging from negative to positive can add seven-and-a-half years to your life, making us a practical example of her research.

Our MEA program is built on three pillars: navigating life transitions, cultivating a sense of purpose, and discovering and embracing your wisdom. The five-day residential workshops at our Baja and Santa Fe campuses are hands-on, with nature serving as a teacher in certain segments. We take pride in having over 5,000 alumni from 48 countries and 28 regional chapters.

Who participates in these conferences?

We host workshops throughout the year in both Baja and Santa Fe, typically involving around twenty diverse individuals from various socioeconomic backgrounds. Many attendees are navigating professional, personal, or spiritual changes and are looking for a supportive community to learn from, as MEA believes that “wisdom is not taught, it’s shared.” After graduation, participants often maintain connections through regular Zoom calls and reunions for months or even years.

Have any participants experienced significant life changes after a retreat?

There are countless transformative stories. We often mention that four key pathways to purpose emerge from things that excite you, challenge you, spark curiosity, or passions from your past that have been overlooked. For instance, a 60-year-old litigation attorney, dissatisfied with the emotional toll of her job, began dreaming about walking on the beach with her late grandmother at our Baja campus. She also recalled her love for baking pies as a teenager. By the end of the week, she decided to explore pastry chef school and ultimately opened a bakery in her neighborhood, finding newfound happiness. We've also seen participants meet in workshops, start businesses together, fall in love and marry, or reconnect with long-lost friends or family members.

What are your thoughts on the emerging trend of “longevity travel”?

Given the aging population and the significant discretionary income among those over 50, I see “longevity travel” as a sustainable trend. For many, this might involve visiting a biohacking resort for experiences like stem-cell regeneration or cryotherapy, focusing on the physical aspects of longevity. At MEA, we advocate for “long life learning,” emphasizing a life that is not only lengthy but also rich in meaning. Our program is centered on the socio-psychological aspects of longevity. I believe midlife wisdom schools, aimed at helping individuals reimagine and repurpose their lives, will be as influential in the future as Canyon Ranch was in the spa industry fifty years ago.

How do you prefer to spend your vacation time?

I cherish places that enable me to connect with my mind, body, and spirit. An ideal vacation includes a mix of education, physical activity, healing bodywork, and perhaps a meeting with a soul healer. I enjoy destinations like Bali, Peru, and Austria, where I can immerse myself in the beautiful lakes, hiking trails, and outdoor culture, especially in summer. I'm also a fan of the medical spa, Mayrlife. Being a hot springs enthusiast, my next adventure is planned for Iceland.