Chip Conley’s ‘surf report’ for 2019

Inexplicably, I’ve taken up surfing in my late 50s. I’m not very good at it, but it has helped improve my vision for the difference between a wave you want to ride versus one you want to pass on. In entrepreneurial terms, this can mean the difference between a long-term trend and a short-term fad.

At age 26, I saw the boutique hotel wave starting to build and created Joie de Vivre. Fifty-two boutique hotels later, I was age 52 and looking for what was next, having sold Joie de Vivre. I got a “wake-up call” from Airbnb co-founder and CEO Brian Chesky nearly six years ago when he asked me to help him “democratize hospitality” and, yet, I’d never heard of the sharing economy at that time. Author William Gibson wrote, “The future is here, it’s just not evenly distributed yet.” So, let me give you my “surf report” for the waves on the horizon that I think are a trend.

Age waves

Two generational age waves are going to seriously affect the hospitality industry for the next few years: millennials and boomers. Let’s start with the younger set as they had a profound influence on the growth of Airbnb and home-sharing.

Two generational age waves are going to seriously affect the hospitality industry for the next few years: millennials and boomers.
Two generational age waves are going to seriously affect the hospitality industry for the next few years: millennials and boomers.

Millennials orient more toward being “outwardly mobile” than “upwardly mobile” – more focused on experiencing the world than necessarily climbing the corporate ladder. This has prompted the growth of the digital nomad, who isn’t looking for a home away from home but instead needs a “home instead of home,” as this traveler doesn’t often have a fixed home or apartment.

While they’re not exclusively young – as evidenced by Airbnb’s most famous guests, senior nomads Debbie and Michael Campbell (who are in their 60s and 70s) – there’s a growing number of people under 40 living a lifetime of bleisure, mixing business and leisure year-round. Software engineers, consultants, entrepreneurs with virtual teams and all kinds of others might spend three months in Bali, three months in Baja, three months in Boston, and then three months in Austin, Texas. As long as they have a solid Wi-Fi connection, their tech devices and an Airbnb account, they’re set.

There are a variety of companies that are servicing these digital nomads: Remote Year, We Roam, Nomad House. Remote Year offers a cohort of 75 random people the ability to “belong anywhere,” traveling for one year staying in 12 different places in the world for a month each, while others offer co-living spaces where you can do an extended-stay working and living in a communal environment. The growing trend of upscale hostels also serves this market. The youth travel market has grown to US$280 billion and accounted for nearly a quarter of all international arrivals in 2017, so this is a big market.

Beyond digital nomad travel, there’s a growing segment of boutique rental operators, also known as branded alternative accommodations or distributed hotels. Think Joie de Vivre meets Airbnb. High touch meets high tech. Sonder, Lyric, The Guild. When you think about the guest experience from the time they leave their home to the time they come home, almost all of their needs are satisfied on their smartphone except when they’re in their hotel.

These companies are changing that. This taps into the growing “more space, less money” trend but has been foreshadowed by the growing need for corporate apartments for relocations and project work. Extended-stay travel has long been one of the fastest-growing segments of the lodging industry, but most travelers don’t find Residence Inn or Embassy Suites as their ideal place to hunker down for a couple weeks so they can “live like a local.”

When it comes to boomers, medical tourism is a growing trend, as we’re all going to live longer, health care costs in the U.S. continue to skyrocket, and medical services in the developing world continue to improve. For not-too-major surgery, it’s also the opportunity to see another part of the world. The global medical tourism market is growing nearly 20% year over year and is expected to be nearly US$50 billion by 2021. Websites like What Clinic and hospitals that are operating like hospitality operators in Asia and Latin America are leading the way.

Transformational travel 

Recently, much has been written about transformational travel – any travel experience that empowers people to make meaningful, lasting changes in their lives. A person’s travel is meant to be a moving experience. It’s the opposite of “vacation,” where you’re essentially vacating your life.

I think there is a new category of travel experiences under the umbrella of transformative travel: midlife wisdom schools. We’re all going to live 10 years longer than our parents, but power is moving 10 years younger in an increasingly digital economy. This has created a midlife “irrelevancy gap” that means many folks in their 40s, 50s and 60s need to imagine how to repurpose themselves.

Society’s outdated model of a three-stage life (learn, earn, retire) taught us that life was a one-tank ride — where we fuel up with curiosity and counsel in our learn period (mostly our teens and early 20s), and burn most of our old school fuel in the earn period. But today, with increased longevity and accelerated changes in the modern workplace, many of us are running on fumes and in need of a midlife pit stop. Life is a two-tank journey, although your mileage may vary.

So, in January, I opened the beta version of the world’s first Modern Elder Academy, on a 3-acre campus one hour north of Cabo San Lucas in Baja California Sur, Mexico, dedicated to helping people navigate their midlife transitions. This idea is hatching elsewhere, as well. Well-regarded marketing CEO Will Travis has created two Elevation Barn retreats in Bali and northern New York where midlife leaders refresh their sense of purpose for the next chapter of their lives.

Much like Mel Zuckerman created a whole new hospitality real estate category to address our growing desire for health and fitness – the destination spa resort – with the launch of Canyon Ranch in Tucson 40 years ago, the midlife wisdom school taps into the long-term trend of high disposable income boomers who want to stay relevant into their golden years.