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A Guide to Taking Two Weeks’ Vacation Without Pissing Off Your Coworkers

It involves doing a lot of work in advance

We’ve talked about vacations from work before — more specifically, how most Americans aren’t taking them. As we noted at the time, a whopping 54 percent of us didn’t take a vacation at all last year, meaning “a grand total of 662 million vacation days withered and died like rotting bananas.”

I’m one of these 54 percent: I haven’t taken more than two consecutive days off for more than 18 months. Why? Two reasons. First, when I take even one sick day, the vibrations and pings lighting up my phone are enough to make me want to smother myself (or the phone) with a pillow. Second, and more importantly, the thought of taking one week — or, God forbid this act of near-treason, two weeks off — means I’ll probably have to work 12-hour days in the weeks, if not months, leading up to said vacation. I would need the vacation, essentially, just to recover from the preparation required to go on vacation. Not to mention all the time it would take to get caught up when I returned to my desk.

But does it have to be this way? Is it really your responsibility to somehow get two weeks ahead on your work before you leave, or is this something your company should be able to cover as part of your so-called paid time off? We turned to Terry Petracca, a human resources professional who has been doing HR for more than 30 years, for some advice.

“The most important thing is understanding what you’re responsible for delivering while you’re away and to make sure it’s as ready as it can be for someone else to pick it up,” says Petracca. “For example, if you’re working on things that have a due date that coincide with your vacation, they should be done before you go.” Same for milestones that rely on your completed work. This way you’re not a bottleneck when you’re gone.

But of course, no matter how well you prepare and how many possible scenarios you’ve considered, emergencies are inevitable. So what do you do? “You have to define what constitutes an emergency and make sure your colleagues agree on that definition,” says Petracca. “Any project you’re on, make sure everyone on your team is fully debriefed. Ask yourself, ‘Is there somebody else who can step in, in case things go south?’ What are they knowledgeable about and what kind of contingency plan have you put in place for them?”

Most of all, make sure any important files are organized and easily accessible. This doesn’t mean, however, you should forward every email you have that could pertain to a given situation, Petracca says. “Be smart about it,” she advises.

Still, no matter how much time and effort you put into preparing for your trip, you may not be able to get away entirely — unless you deliberately choose somewhere with terrible cell service and no wi-fi. That’s because, according to Petracca, it’s “not unreasonable” for your manager or members from your team to ask that you check your email before you start your day. “Actually, that preserves your sanity,” says Petracca. “Because when you get back, you won’t have 500 emails to go through.”

Speaking of that solemn first day back at the office, there are three important things to keep in mind, according to Petracca:

  1. If you can, check your email the night before and clear some of them out before you get in, since people are going to want to grab you the minute you get back.
  2. Immediately find the people who you’ve asked to help take care of your daily tasks and make sure everything went smoothly.
  3. Everyone appreciates a gift from the area you visited, like macadamia nuts, coffee and/or booze.

So there you have it: Helpful, if extraordinarily depressing advice for how to get ready to go on vacation in a country where paid time off isn’t even a legal requirement. Have a fun trip — if you ever make it out the front door!