These are the secrets of constant holidaymakers

Meet the people who've figured out how to take months off from work each year without jeopardising their careers or annoying the people they work with.

When Chris Lang’s company switched to an unlimited vacation policy, he doubled down on taking time off, carefully planning days away while delegating to his staff and encouraging others to do so as well.

As an executive, he had always carefully watched how much time he took off and was worried about how to take advantage on his European company’s generous policy without causing everyone else to fall behind.

“The biggest thing is to really trust your coworkers will pick up your slack,” he says.

The strategy is paying off. As the president of the US division of Bynder, an Amsterdam-based marketing software firm, Lang has managed to take more time off while exceeding revenue goals. Last year, he spent six weeks out of the office (compared to three the previous year). He plans to take eight weeks off this year.

“One of the hardest things about taking vacation is figuring out when you’re going to do it,” says Lang, who is based in Boston.  

Thanks in part to unlimited holiday policies, more of us are finding that taking lots of time off doesn’t have to jeopardise our careers or hinder getting promoted. And with constant holidaymakers flitting back in from a trip to Spain one month and off to the States the next, there are the envious among us who can’t seem to manage to even take a normal amount of time away.

So what’s their secret?

“You have to tell yourself that we’re not necessarily saving lives here,” he says. “It might seem like the end of the world [to be away], but it’s not.”

To be sure, time off policies vary widely across the world, and many of us still feel that taking a vacation can be the opposite of relaxing. While at least five weeks of annual leave is standard in the UK and across much of Europe; in some cases time off is required by law. Many US companies give employees two or three weeks off per year, but that’s discretionary from company to company and not required by law.

Working across countries can make it difficult for some to prioritise taking their leave, says Rachel Mason, a marketing manager for 33Talent, a recruiting firm in Singapore.

“My Singaporean friends don’t always use up their leave allowance each year,” says the 27-year-old, who moved from the UK and explains that it’s frowned upon culturally. “My friends working in the UK always use up their leave, even if just to stay at home and have a few days off.”

Worry about yourself

For many of us, worrying about what others might think is the biggest obstacle for taking time off.

That leads to trying to slip away, almost in secret. But, those who are smart about it are upfront about time away. That helps to build a sense of transparency, says Jacob Shriar, 29, director of content at Gsoft in Montreal, Canada. Before Shriar leaves, he mentions it to his team four days in a row at a daily meeting and writes it down on a shared white board.

“I’ll try my best to forewarn people,” says Shriar, who recently took time away in Barcelona and New York. Setting the example when leaving the office helps others feel better about taking their time away, he adds.

Work hard, play hard

For Tyler Maynard, head of sales at catering company CaterCow, goals are a benchmark for when and how he takes time off. He sets aside time for a two-or-three week stint away, but he’s also gotten creative with other time away from his desk.

The former investment banker takes advantage of CaterCow’s policy allowing employees to spend three months a year working remotely (this year he’ll use his time to ski in Vermont and visit Columbia) by rethinking his workdays. The months he works remotely, a typical nine-hour-day of work can be done in six hours without the normal meetings and commuting. If he starts early, that leaves the afternoon free to relax in his holiday locale.

To make certain he’s focused on work and not the slopes or exploring while in a remote location, Maynard incentivises himself. “I’ll set carrots for myself and say, ‘This is what I want to accomplish today,” he says.

Constant vacationers have another secret to successfully being away from work. They don’t make every day off around a grand plan, says Shriar. Instead, one-off days can serve as a catch-up for your social life, quick impromptu trips with friends, or much-needed mental health breaks after a few challenging weeks at the office, Shriar says.

“I don’t like the idea of pushing yourself to the limit, there’s only so much your brain can handle before making mistakes,” he adds.

Craft an out-of-office strategy

Of course, work emergencies and must-answer calls will crop up no matter where in the world you are and despite how much time you have off. The trick is to be smart about how to handle them when they do arise.

Before you go on leave, establish ground rules for contact, Mason says. For instance, she’s sure to spell out how and when colleagues can reach her, whether or not they should expect her to check emails (along with how often she will do so).

Most of the time, Mason uses longer holidays (such as one she recently took to Australia) to completely disconnect, but she checks in when taking quick trips or three-day weekends.

Transitioning back to the office

All good things come to an end. Easing back into the work helps with minimise the jolt of back-to-office blues that constant vacationers can suffer. When Denise Twum, 34, a manager at Issuu, a magazine-publishing platform, goes away, she leaves a spreadsheet that assigns colleagues to complete tasks that she needs to hand off.

When she returns to her Palo Alto, California, office from two weeks touring South Korea or visiting relatives in Ghana, for instance, she leaves herself the weekend to re-establish a routine, catch up on emails and check the spreadsheet to see where she needs to pick up before heading back in to work on Monday morning, making the transition more seamless.

Getting up to speed before she gets in the office helps squash work-related stress and allows her set priorities without feeling overwhelmed, she says.  “I have the weekend to catch up on all of the things going on, and figure out how to talk to coworkers about [it]…I make sure to start on a good note.”

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