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Holiday Vacations Without Guilt

Vacations for entrepreneurs are different—but they can, and should, be done. Here are some tips for enjoying your time off in the most stress-free way.

Holiday Vacations Without Guilt

Executives of all levels often choose to skip vacations each year. Increasingly, however, those who do get away for a holiday seem to favor a complete break from the office during their time away. A June 2012 survey from staffing firm Robert Half Management Resources shows an increasing number of executives do not check in with their offices during vacation—in fact, a surprising 51 percent do not check in at all. This figure is nearly double a similar poll in 2010 (26 percent) and up significantly from the same study in 2005 (21 percent).

As an executive in the travel industry, I am fortunate to be able to travel often, both for business and pleasure. This past summer I took my family to Europe. While we were gone, I tried to unplug from the day-to-day work issues and took the opportunity to think strategically about our company and industry, something I always find easier to do from a distance.

If, like me, you are one of the 49% of executives who must check in and who can’t entirely leave work behind, consider the following tips to make your vacation more successful and enjoyable for you, for your family and for your organizational team.

Set specific times to work. I prefer to work early in the morning when I’m on vacation. My family tends to want to sleep in and it is the perfect time to return email, check in, and perhaps leave a few voicemails so my team knows I’m still engaged. If there are must-do projects on your plate, let your team know in advance when you will be available. Some projects are important enough that even when I’m in Europe my team will do whatever is necessary to catch me on the phone. Just as importantly, let your family know when you will be unavailable. If you plan an activity with them, unplug and be present. I have a friend whose family has an entire album of her on the phone during vacations. Unlike my friend, enjoy the unique opportunities that vacations present to spend quality time with your family and friends—that’s what it is all about!

Set ground rules. Discuss with your team what you want to be kept in the loop on, and what you expect them to handle without you. Give them the opportunity to make decisions on things you would normally oversee. Allow some mistakes to let them grow. Try to think of it as a growth opportunity for your team, not a risk. Set parameters about important projects or topics. Even when I’m gone, I ask my teams to send me a written weekly update in lieu of our weekly sit-downs. That way I can catch anything that might need my attention.

Find a private place to work. Don’t be "that guy"—you know the one with the wireless headset having the "oh so important" loud conversation on the airplane or at the hotel pool. Find a private corner of the hotel, or better yet, rent a vacation home with an extra room or office that you can use as your vacation office. I love the ability to set up once and not have my laptop station also be the breakfast station, changing station, and shopping bag drop station.

Don’t let work dominate your vacation. Your kids will grow up fast, and some of these vacations will provide the opportunity to create some of your most cherished memories with them. Work will still be there when you return. Take the chance to unplug, unwind, and leave everything behind. If you do choose not to check in regularly on vacation, as over 50 percent of executives did this year, don’t think the world will end. You hired capable people. Give them a chance to experience life without you. Often you’ll be surprised by what they can accomplish during the time you are gone.

—Julian Castelli is the CEO and founder of VacationRoost.

[Image: Flicker user santheo]