How Entrepreneurs Vacation Differently

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Entrepreneurs see vacations as a chance to experience new places and people and encounter outside perspectives.

As someone who's been in the startup game for a while, you know entrepreneurs tend to experience vacations a little differently.

It's often difficult to leave your company unattended for two or three weeks. And you're not alone. According to the 2013 Sage Reinvention of Small Business Study, 43 percent of small-business owners are spending less time on vacation than they did five years ago.

That's the strange dichotomy of being an entrepreneur: Your schedule is flexible, but you also have things you simply can't ignore. Although you're technically on vacation, you know there will be days when you'll need to put in a few hours of work. And when a typical vacationer spots you typing away in the hotel lounge, he'll think, "How sad; he doesn't know how to enjoy his vacation properly."

But the funny thing is, you're content knowing your efforts allow you to run your own company and do something you enjoy. In fact, you feel bad for the sorry saps who only get to enjoy themselves for two or three weeks out of the year.

Value Experience Versus Escape

When entrepreneurs head out into the world, they approach downtime from a different perspective. To them, a vacation isn't some escape from the stresses of work and home; it's an opportunity for adventure and experience.

The word vacation itself has this "getting away" connotation, like being on furlough from prison. Instead I prefer the word trip. When you take a trip, it's not about getting away from something--it's about choosing to do something different for a certain period of time. Different is good; it breeds innovation and fresh ideas.

That's not to say you shouldn't use your trip to recharge your batteries. Rest and relaxation keep you healthy. But you should view your adventure as a chance to experience new places and people and encounter outside perspectives, not to nap poolside.

These new experiences will not only help you improve as a person, but they'll also inform new ideas for your business. I can't tell you how many of my best ideas have come to me while traveling.

Stop Planning, and Start Rolling With the Punches

As an entrepreneur, you probably plan your trips the same way you plan new business ventures--by considering as many angles as possible while planning for any of them to go awry.

This makes you a hearty traveler who's always able to make the best out of a bad situation. The typical vacationer has bad trips and good ones. But you thrive in uncertainty and walk away from even the most dismal adventures with lessons learned and stories to tell.

A recent trip I took serves as an excellent example. I was in Vietnam with a friend, and he convinced me that we should head over to Cambodia. The country wasn't all that high on my bucket list, but being an entrepreneur and ready for new experiences, I said, "Why not?"

To make a long story short, I saw a lot of beautiful country, partied admirably, became dangerously dehydrated, closed a major deal with Mark Cuban, went to the hospital (twice), and walked away from the whole thing thinking, "Wow, this is going to be an amazing memory." Compare that to your neighbor's last vacation at a five-star resort in Hawaii. It was probably fantastic, but was it the adventure of a lifetime?

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Stephan Aarstol is an American internet entrepreneur and author of the book The Five Hour Workday, which is based on Tower Paddle Boards' invention of the 5-hour workday in 2015 that would eventually spread the idea to over 10 million people worldwide. Since founding Tower in 2010, it has gone on to become one of America's fastest growing companies and Mark Cuban's best investment in the history of Shark Tank. Tower has diversified into a direct to consumer electric bike company called Tower Electric Bikes, a beachfront event venue called Tower Beach Club, and, where consumers can shop all the world's finest direct to consumer brands from one easy place.