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Vacations at Work

Why This CEO Says You Should Take At Least 3 Vacations a Year

Posted January 9, 2018 By Andrew Littlefield

When Jamie DeBole and his co-founders set out to start their company, GlobeKick, they had a very specific idea about how they were going to solve what they saw as a big problem with today’s young professionals: they craved meaning and connection in their work, but weren’t finding it.

But like most entrepreneurs, they realized after a few attempts that they were going to have to change their approach.

The original idea for GlobeKick was to take young professionals with the ability to work remotely on multi-month trips around the world, where they could still work full-time while immersing themselves in a foreign culture.

The problem? It’s hard to fully commit to a full day’s work while sitting in a coworking space located on the other side of the globe. After all, you didn’t endure a 14-hour plane ride just to sit on the computer all day.

Now GlobeKick takes travelers on more frequent, shorter trips—three a year, in fact. And rather than aim for maximum productivity on the road, the goal is disconnection.

The result is a recharged worker with a new, global perspective—someone employers are eager to have on their own teams.

Editor’s Note: this interview has been edited for brevity and clarity.


Andrew Littlefield: Tell me about how GlobeKick got started.

Jamie DeBole: We set out to create travel adventures that we wish had existed. Our founders had come from a relatively corporate world—I’m the only exclusion to that. One of our co-founders got his J.D. here at the University of Texas at Austin and the other got his M.B.A. at UT as well.


Travel Company CEO

GlobeKick founding team, with CEO Jamie DeBole, front.

They were doing quite well, but ultimately were yearning for something more. A lack of flexibility in their office environments drove them away from the office and towards travel. One of my co-founders and I traveled through four continents together over the course of three months, and we met our third co-founder down in Australia.

We all linked back here in Austin, Texas and got to talking about the overarching statistics of millennial office workers, which are striking. Millennials are changing jobs every 26 months on average. 92% of them say that the number one thing they’re looking for in their next job is workplace flexibility. We asked ourselves how could we help more people solve this problem?


AL: What is it about traveling that helps scratch this itch?

JD: People are lacking this depth of community around shared experiences, and we found that you can get very intense, deep shared experiences through international travel. You’re slightly vulnerable, it’s a new environment, you’re with new people, and the depth of connection that you can make during that period of time can be much deeper than in a normal day-to-day environment.

We want to have shared, meaningful experiences to create that depth, create that bond. It’s not dissimilar from your colleagues. You might work around them all day, but outside the office, you don’t spend any time together.


Trip to Morocco

Globekick travelers in Morroco


AL: Why did you decide to move away from long-term, remote-working trips and move towards shorter, more disconnected trips?

JD: It can be difficult to fully immerse yourself in the experience and fully engage in the work. There’s a lengthy adjustment period. So frankly, I find it quite difficult to work more than a productive four to five hours a day without it starting to feel like it’s intrusive and challenging.

We initially said, “All right. All these people are working from home environments, but they’re feeling isolated, they’re feeling lonely.” So originally, we were pursuing a solution through remote work.


GlobeKick in the Caribbean

Biking in the Caribbean


But we no longer see this (extended remote work) as the future. After having done this for 18, 19 months, and having serviced a large volume of people in a really helpful way, I don’t think it’s sustainable. Three months away is a long time for anybody, even if you do have a job that allows you to work remotely.

So instead, this year we’re going to have three trips, each one week long. We take care of the housing, we take care of the adventure elements, we take care of a lot of the knicks and knacks. You’re just responsible for the flights. And the reason for this, and why it’s relevant potentially to your readers, is that busy working professionals don’t have time to plan these kinds of adventures. But they want to go. They say “tell me where I’m going, when, and I’d love to go.”


AL: What will those trips be?

JD: This year, we’re heading to Morocco for a week trip, including camping in the Sahara Desert underneath the stars, camel trek in, camel trek out, and a night in Marrakesh, Morocco on either end. And then we’re going to head down to the San Blas Islands to do some sailing in the Caribbean between Panama and Colombia, and then end the year in Cambodia on a volunteering mission working with endangered elephants on an elephant sanctuary.


GlobeKick in Cambodia

Volunteering at an elephant sanctuary


AL: Why should an employer support their workers doing trips like this?

JD: An office environment is all about teamwork. The stronger the team the higher output, the higher the performance. And we found that if you can bind people together and create some accountability to one another in a personal way, then collective output increases.

If you feel connected to those you’re working with and around, then you’re going to be a lot more invested in the overall goals. I think there’s a lot of benefits both from attracting and retaining (talent), and providing a key differentiator—making your employees or your members happier and more connected.


AL: What’s a common thing you hear from people after these trips?

JD: That they didn’t know how much they needed a shakeup of their current life—a change in perspective. Everyone’s been very, very happy that they went. The people you meet make friendships that last a lifetime because of that shared experience.


Travel for Millennials


AL: What’s something you know now that you wish you knew five years ago?

JD: That everything you see in the world is created by people no smarter than you and me. And so, if you have a dream, you have a vision, you have a passion, pursue it because tomorrow won’t wait.


Member invitations to join GlobeKick for 2018 will be officially released on February, 5th.
Until that time, GlobeKick is only accepting 100 new members for consideration at a special pre-launch price of $750 for its full membership of benefits.

For consideration of pre-launch invitation, click here to submit your request, and use code CONVENE2018


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