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If you really must work on vacation, here’s how to do it

Yes, you’re supposed to disconnect. But sometimes, work is unavoidable when you’re on vacation. Here’s how to get things done and still have fun.

If you really must work on vacation, here’s how to do it
[Photo: Roopak Ravi/Unsplash]

You’re finally getting around to taking that vacation. But whether it’s an important project or a last-minute fire drill, as your departure date gets closer and closer, it’s clear that some of your work is going to encroach on your time away.

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If so, you’re not alone. A May 2018 survey by staffing firm Accountemps found that 56% of workers will connect with the office during their break. And while we all know the economic and career benefits of vacation, sometimes taking care of business on your break is unavoidable.

“I’m not one of those persons who says you should never do any work on a vacation. On the other hand, it’s obviously clear that it’s a slippery slope, so you must find some way so that the expectations don’t become that you’re going do this on any kind of regular basis, because that will defeat the purpose,” says John de Graaf, founder of Take Back Your Time, an organization that advocates against the culture of overwork in our society, and author of Take Back Your Time: Fighting Overwork and Time Poverty in America.

So, how can you do what you need to do and still feel like you got a break? Here are some tips to keep in mind.

Create a getaway plan

It may be too late to devote weeks to planning your getaway, but ideally, you would start thinking at least a few weeks ahead about deadlines and what will need to be covered while you’re out, says leadership expert Holly Dowling. And give people at least two weeks’ warning that you’re going to be out of office. Use key opportunities like staff or project meetings to remind them, as well as manage expectations about being disconnected.


Related: Is it possible to totally unplug on vacation?


“Communicate with each other, your teams and everyone you’re serving,” she says. “Don’t just throw it out there on your out of office,” she says.

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If possible, plan an easing-down period the week before where you ruthlessly prioritize the most important tasks to be done, de Graaf says. It’s not always possible, but if you can focus on the essential tasks, the others may more likely be delegated or delayed until your return.

Cross-training others is also important so that you can get a break, de Graaf adds. He says that cross-training allows employees to step in and cover for each other, which benefits both the individual on leave or vacation and the organization.

Tap your work fam

If you work in an office, you may have a colleague or an assistant who can filter inquiries while you’re out to ensure that you’re not contacted unless necessary, says HR specialist Melina Gillies with Sales Up! Business Coaching in Ontario. Obviously, communicate that plan to the person so the inquiries are not a surprise, she adds. If you work on your own, enlist the help of a virtual assistant or trusted colleague to field inquiries while you’re gone.

Then, you need to trust your team, she says. They’ll know the difference between a “five-alarm fire” and inquiries that can wait, she says. But having a buffer between you and clients or coworkers can help ensure you don’t feel compelled to answer every email or text message.

Use tech

Obviously, it’s a good idea to set auto-responders and outgoing voicemail messages with information about your departure, return, and interim contact person. Also, turn off notifications across the many platforms you may use, such as Slack, Trello, and others, otherwise you may find yourself with regular distractions that can make it hard to focus, Dowling says. Use your phone’s “do not disturb” option when you’re with family or during times when you really don’t want to be bothered.

Set boundaries

When work crops up, “get it out of the way early so you can enjoy your time off to the fullest,” says online branding expert Brandon Loures, founder of Brand Lift Digital Marketing in San Diego. Give work an hour or two of your early-morning time, and then let it go.

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Related: How to check email on vacation and still enjoy yourself


De Graaf agrees with limiting your time to specific limits per day or week, but also suggests a looser approach. If everyone in your group is taking an afternoon nap, use that time. If you are a night owl and stay up later than others, catch up on email messages then. Find the windows of time that will be least disruptive to your family or friends, he says. If you must interact with coworkers, let them know the times of day you’ll be checking your email, as well as when you’re completely unavailable, so they know when to expect a response and don’t keep trying to contact you.

But whatever you do, don’t drag your fellow vacationers into your work travails, Loures warns. “Other people don’t want to hear about your work, and you don’t want to make it the center of your vacation,” he says. “Make time to do it somewhere quiet where you can be super productive. You will be amazed at how much real work you can do in one hour when your motivation is to go on an epic adventure as soon as you are done.”

Address distractions

As cofounder of the boutique intellectual property law firm, Kim Winston, LLP in Yonkers, New York, attorney Laura Winston often finds herself in need of answering a few calls or email messages while she’s away. And while she tries to maintain boundaries, she has one rule that supersedes them: “Anything that’s mentally distracting me from my vacation must be addressed, even if it’s not a deadline issue,” she says.

Recently, she took a week to learn glass blowing. And while she had her team in place, managed expectations, and set boundaries, her mind kept drifting to one piece of unfinished business. “On the first day, there was just this one project that was looming in my mind, and it was not something that was an urgent deadline issue, it was more of a client relations issue,” she says. That evening, she took some time to tie up the loose ends that were bothering her, so she was able to put aside the distraction and focus on her new hobby. If something is truly bothering you, just deal with it so you can get back to your time off.

Remind yourself about priorities

Vacation isn’t something you do to impose on your coworkers. Remind yourself about the important reasons you’re taking some time off, Gillies says. Aside from the benefits to your well-being, focus, and creativity, you need to have a life outside of work.

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“But you really also need to be driven and focused in the playtime that you’re giving yourself and your family. You’re still trying to make memories and build that successful personal life,” she says. If you have a “work hard, play hard” mentality, don’t leave out the “play hard” part. Treat making memories and spending time with family and friends as seriously as you do your work—or you might end up regretting it later.

If it’s possible to plan a light day on your return, that’s a good idea to help you ease back into work, Dowling says. And if the culture of your company makes it difficult to take vacation without repeatedly being dragged into work issues, that’s a leadership issue, de Graaf says. Use feedback mechanisms such as employee surveys to share that concern with your company’s leadership team.

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About the author

Gwen Moran writes about business, money and assorted other topics for leading publications and websites. She was named a Small Business Influencer Awards Top 100 Champion in 2015, 2014, and 2012 and is the co-author of The Complete Idiot's Guide to Business Plans (Alpha, 2010), and several other books

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