The Great Escape: Getaway’s CEO Jon Staff Makes Unplugging Easy

Jon Staff swears he had a midlife crisis at 25. A graduate of Harvard business school, he had already started several companies but was feeling listless. “I realized I was burned out and didn't care about the things I was working so hard to create,” Staff says. A friend loaned him a 26-foot Airstream trailer, in which he traveled the American West for five months, covering 8,000 miles. On that meandering trip, Staff encountered Americans living in tiny houses, dwellings under 400 square feet that prioritize the bare necessities in order to have a low ecological footprint. He was enamored. What seemed like a personal revelation turned into Staff’s next venture.

“I wanted to have one to escape to once I returned to life back in the city. What I wanted for myself was no WIFI, a sacred place where I wouldn't do work, and I hoped nobody would bother me. I was searching for free time, for disconnected time, and for time to reflect,” Staff says. “I didn't have any money to buy or build even one tiny house, so I decided to start a company and raise some seed capital. Fortunately, I’m not as unique as I might have thought, and other people were searching for the same things.”

A year later, in the spring of 2015, Staff launched Getaway. What began as a trio of cabins outside of Boston has since swelled into a national network of tiny homes strategically located about two hours from the country’s major metros. There are 28 Getaway Outposts to date—more than double the number of destinations the company offered in 2020. Locales range from the PNW Skagit Valley to Hampshire County in Massachusetts, from Minnesota’s Kettle River to the Texas Hill Country. With each site hosting 30-40 cabins, Getaway’s cumulative cabin count has now crossed 1,000.

Naturally, that’s not where Staff’s vision ends. This summer, Getaway is launching Campgrounds, professionally prepared tented campsites with comfortable amenities like mattresses, modern bathrooms, covered kitchenettes, hammocks, and private bathroom suites. Some may call it “glamping.” Staff has also penned a book, Getting Away, which captures his ethos of and ideas for preserving one’s mental health through practices like taking baths, subscribing to the print edition, and audibly voicing the end of your work day.

We spoke with Jon Staff about his escapist empire and why we all need to unplug–that goes for you, too.

"What I wanted for myself was no WIFI, a sacred place where I wouldn't do work, and I hoped nobody would bother me. I was searching for free time, for disconnected time, and for time to reflect."

01. Did you grow up camping?

I grew up in a cabin my parents built by hand on a small lake with just four houses on the Mississippi River, right where the Mississippi stops flowing north and turns south to New Orleans. My childhood was in nature: my days and years were spent around a campfire, roaming the woods, and combing the beaches and marshes. I remember most fondly watching freighters by firelight from a beach on Lake Superior accessible only by boat.

02. You tie the professional success of yourself and your employees to the ability to unplug and escape from work. What happens when we truly put our professional selves on the back burner?

It's an overused word but it is about balance. If we're using your analogy, it’s about putting work on the back burner sometimes. Sometimes work is on the front burner–that’s often the reality for many of us. The problem is too many of us leave it on the front burner all the time, and furthermore keep filling the pot with more and more and turning the heat higher and higher. Moving work to the back burner allows you to put something else on the front burner: maybe your health, maybe your family, maybe your curiosity. It helps work, too–the sauce only gets good if you give it time to simmer. We can't leave our work life to boil all the time and expect something meaningful to come of it–it might be hot, but often it bubbles over and makes a mess.

“Moving work to the back burner allows you to put something else on the front burner: maybe your health, maybe your family, maybe your curiosity."

03. How does making time like this affect you as a leader?

It happens over and over in my life. I'll put work aside and go for a long hike somewhere. I have no intentions for that hike. But what ends up happening is that I figure stuff out. I come up with an idea. I sort out some feelings. The point of disconnecting is not to come up with new ideas for work, but it happens and we can't control it–letting our minds wander allows our brain to process in different ways, ways that include but are not limited to our work lives.

04. What makes Getaway different from Airbnb with some digital self-restraint?

Getaway designs, builds, owns, and operates all of our Outposts, and we're obsessive about consistency and allowing guests to have great experiences, so you always know what you are going to get. We are also different from most other hospitality providers in that we are explicitly not laissez-faire about how you spend your time: we have a strong point of view about what Getaway is meant for and that is, ideally, doing nothing.

Our design philosophy is everything you need and nothing you don't, so you don't need to pack much. Getaway provides really nice linens and bedding, a fully stocked kitchen, shower supplies, s'mores, and firewood.

05. Are there plans to add any other experiences to the Getaway offering? What’s next?

We're about to roll out an enhanced food and beverage offering that will allow our guests to get fresh food delivered to their cabin before they arrive. We're also working on a program to allow folks to check in earlier or stay later.

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