How to Leave Behind Work & Take a Real Vacation

UPDATED: October 10, 2015
PUBLISHED: May 15, 2015

Small-business owners and corporate employees are often reluctant to take vacations because they worry that their companies will suffer while they’re away. But Paul Howard, a co-owner of Cliff Bell’s jazz club in Detroit, has learned that leaving is advantageous. “The farthest I’ve gone is a bike trip to the Andes, cut off from all communications—except for occasional Internet café—for five days. And what I found… is that people step up and learn things they didn’t know before. So when I got back, there was one more thing I didn’t have to do. It was a really beneficial process.”

Howard seems to be in the minority, though. Americans are terrible about using vacation time and terrible about fully escaping office responsibilities when they do take time off. While on a camping trip, Don Gibson, dean of the business school at Fairfield University in Connecticut, was “shouting into a cellphone, trying to make a connection with a reporter so he could meet a deadline. I’ve also done talk-show interviews in the middle of vacations…. I rarely take all of my time.”

Steve Jobs, when he helmed Apple, was famous for calling employees back from vacation, says Yukari Kane, author of Haunted Empire. His successor, Tim Cook, while equally driven, “understands that people need to take vacations,” Kane says.

A Manta survey of 1,200 small-business owners released in 2012 found that nearly half don’t have time for a vacation, and seven of 10 will check email and documents on their phones while gone. As for corporate workers, a 2013 survey commissioned by Ricoh Americas found that 54 percent of workers say their bosses expect them to do at least some work on vacation. “Americans are work martyrs,” according to the U.S. Travel Association, which found that in 2013, Americans averaged 16 annual vacation days, down from 20.3 in 2000. That’s the least time off in the past four decades, the association said, and 40 percent of those martyrs said they didn’t go because they worried about returning to a mountain of work.

With our tips, a getaway is a possible dream, giving you relaxation that will make you a more productive boss or worker and returning you to a manageable workload.

OK, Everybody Out!

If you’re the owner or CEO, perhaps you can shut down the business for a few days. That builds goodwill among employees, which is the exact opposite of what happens when reluctant staffers have to sit in an empty office. A member of a four-person marketing company told the organization Ask a Manager, “There was no reason for us to be there [between Christmas and New Year’s Day]. The phone literally never rang. No emails came in. All our clients were closed. I caught up on some work, but I really resented sitting in a chair for eight hours while friends and family were free.”

Anne Weisberg, senior vice president at the Families and Work Institute and co-author of Mass Career Customization, points out that there’s no reason to check in with the office if everyone’s taking the same time off—and that even major corporations use this approach. “Several companies, including PricewaterhouseCoopers and GlaxoSmithKline, close down the week between Christmas and New Year’s,” Weisberg said. “Everyone is out at the same time, which means no one is worried about their colleagues trying to reach them. What if you did this for your company’s slowest time of the year?” (And, P.S., a PricewaterhouseCoopers news release applauds the break: “Giving our people the chance to relax and recharge helps them deliver at a high level in the new year.”)

Mary Beth Harris uses this tactic intermittently at her AVA Restaurant and Wine Bar in Staunton, Va. She shut down for a “giving-back day” between Christmas and New Year’s in 2014 and catered a special meal for 20 at a local women’s shelter. Because downtown Staunton “can be a bit sleepy” over the holidays, she also closed on Christmas Day and New Year’s Eve—with plans for quality time with her family (and her third chance to watch the Big Apple ball drop in 14 years).

“It’s really difficult to get away when you’re both the chef and the owner,” says Harris, who has six employees, some of them servers cross-trained to also work in the kitchen if needed. When duty called for a recent wedding in Texas, she closed and took her prep cook—whose son lives in Austin—along for the ride. And she looks for slow times, like March and August, to close for a full week.


If you can’t shut down, well-in-advance planning is crucial for taking time off and not having to meddle in the business while you’re away. You need to clear your calendar and make sure you won’t be out of pocket at the same time as the people—from your assistant manager to your brother to corporate colleagues—who can cover for you.

The penalties of not having backup are clear. Vacationing information technology professionals know all about the urgent call from the office—the website’s down, and you’re the only one with the fix. In Computerworld, Michael Adler, then with Symantec, describes a trip in which he set up a command post in a local library for seven hours of intense work. “It’s not healthy,” he says. “I literally lost a Friday of my vacation week, and I was supposed to be on the beach.” That wouldn’t have happened if Adler’s IT team had delegated responsibility for crashes or other crises beforehand.

To execute this tactic effectively: If possible, spread the responsibility so one person isn’t stuck with the full burden of replacing the vacationer as well as doing his or her own job. With point people assigned in your absence for crisis and non-crisis work, if-then scenarios can be determined, problems can be solved, and work can progress; final approval of new work will wait for your return. These arrangements let “people actually unplug on vacation,” Weisberg says. “The tighter the coordination among team members, the more likely that people will actually get a break.”

Howard Kamens, who runs the small marketing company WordRage from his home in Palm Springs, Calif., says the key to getting away is collaboration with other, simpatico one-person shops. “We’ve developed a détente. Our skills overlap, and we’re all aware that we each need to take a vacation now and then. So if something comes up that has to be handled, these other people can deal with it—and they do. It’s totally reciprocal. Our motto is: ‘We’ll figure it out.’ ” Even though they cooperate and compete, the friendly rivals figure that everyone will get a turn, benefiting from referrals and from being able to take vacations.

When no one on hand can fill your shoes, consider temp agencies, which supply workers at all levels of expertise and experience. Some—like Carlsen Resources, Business Talent Group and Nielsen Healthcare Group—offer “executive on demand” services. But be sure to rent talent at the precise level you need so you don’t overpay. A temping CEO (often a retiree who wants a change from golfing) can command $1,000 to $2,000 per day, according to

Other Getaway Tactics

Sometimes you just have to compromise. You take that trip, but:

• Set up a brief window—say, an hour or two early in the morning—when you can be contacted without interrupting the main flow of your time off.

• Leave for less than a full week. Stephanie Marston, a stress/work-life expert and consultant with Toyota, McDonald’s and others, advises that a long weekend might be just the thing to recharge depleted batteries. “Take a mini-vacation. There is very little in life that requires your immediate attention…. With rare exceptions, most things can wait until tomorrow.”

• Enlist technology. Jay Ragusa, owner of Gofer Ice Cream, a four-chain store in Connecticut that has up to 35 employees in the busy months, has figured out how to work remotely with just his smartphone. “I can see the cameras and make sure that the store was opened up and people are working. And I  have access to the register to see the sales.”

Turn Off That Email!

OK, you’re gone. How do you stay off the grid?

Tom Murphy, former chief information officer at Royal Caribbean International and now CIO at the University of Pennsylvania, temporarily shut down his email account during a two-week trip to Hawaii. “People got messages with my cellphone number so they could reach me in an emergency, but nobody dared. I went on vacation, disconnected, and the world didn’t stop,” says Murphy, who admits to being “that Type-A, driven businessperson who thinks the office can’t get along without me.”

Maura Thomas, who is founder of and author of Personal Productivity Secrets, heartily endorses a temporary shutdown of your cellphone’s email and social media push notifications. “White-collar professionals tell me they can’t take vacations because work piles up while they’re away so they just have to work harder when they get back.… A fresh perspective can’t be achieved if employees never fully disconnect from work. Inspiration, creativity and motivation are depletable resources.”

Thomas suggests this tactic for easing the transitions: Set up your out-of-office messages to say you’re leaving a day earlier and coming back a day later than you actually do. This maneuver creates breathing room to finish last-minute work before you leave and re-entry time after you return.

To avoid temptation, consider removing email from your own control. Teri Hockett, a transitional career strategist and CEO of What’s For Work, says “many spouses specifically chose vacation spots where there was limited to no cell service or Internet connections to ensure that they received undivided attention. We have fewer and fewer options for those types of vacations [because access is now so widespread], so people have to make a conscious effort to make arrangements to be inaccessible.”

Brad Lowrey did exactly that as a public relations executive at Weber Shandwick. After one vacation was ruined by work commitments, Lowrey says, “I found a cabin in the middle of nowhere in Tennessee where I could see on the coverage map there wouldn’t be mobile service, and it was accurate.”

Lowrey sneaked into town to get his connectivity fix. “And you know what? Every time I checked, everything was fine. Even better, I actually remembered what it was like to not constantly be on my phone or computer and how nice it was to just hang out with my wife and my boys. So much so that we’re planning another disconnect trip this year.”

One communications manager, who asked not to be identified, advises vacationers to “put your computer in your briefcase and leave it there.” Attempt even one remote intervention in a work situation, she says, and it’s inevitable that you will get sucked in. “Worse, people will get the wrong idea—that you will always be available, and requests while you’re out of the office will only escalate. You’re also doing a big disservice to your co-workers because of heightened expectations for everyone else. Working while on vacation is like coming to the office with the flu—you’ll only give the bug to everyone else.”

To emphasize the need for unplugging completely, Thomas offers another analogy: “Working on vacation is like taking a phone call while you’re playing golf—it throws off concentration, and your game falls apart.”

Overscheduled? Learn 7 ways to take back your day, your week and your life.