Make the Most of Your Vacation When You Can’t Fully Unplug

by Elizabeth Grace Saunders

July 29, 2024

Although working during vacation isn’t ideal, there may be times when projects, deadlines, or client obligations prevent you from being fully offline. While it’s not easy to balance these competing priorities, it is possible to get critical work done while enjoying some refreshing time off. The key is to do a little pre-planning, making sure to avoid a few common mistakes people make when mixing business and personal travel. The author presents five pitfalls to avoid on your working vacation — and what to do instead.

While advice abounds on the importance of fully unplugging during your hard-earned time off — and for good reason! — what should you do if you’re in a situation where you can’t be fully offline? Maybe you’re a lawyer prepping for a big trial, an investor closing a deal, a sales executive closing out the quarter, or someone else with a non-negotiable, critical deadline. But you really want to feel like you got some refreshing time away.

It’s not easy to balance these competing priorities, but it is possible.

As a time management coach, I’ve observed five common ways people sabotage their summer travel plans when mixing business and pleasure. Here are five pitfalls to avoid — and what to do instead.

Even if you plan to work during some of your time away, you can take tremendous pressure off of yourself by letting people know that you’re out of the office. If you’re traveling during business hours, put up your out-of-office message while you’re in transit. Do the same for any days where you’re not planning to be online for the full day.

You may be tempted to not let people know that you’re on the road with the rationale of, I’ll just check messages when I have some downtime at the airport before takeoff or once I get to the hotel or after we go to dinner.

But if you don’t let people know you’re out, you’ll get more and more tense when you realize that, thanks to a traffic jam, you’re stepping on the plane right before the doors close (oh, and the in-flight wifi isn’t working properly), or when collecting your rental car takes much longer than expected, or when the service is so slow at the restaurant that you get back from dinner a couple of hours late and feel too exhausted to do anything. Instead of being calm on your travel day, you’re muttering choice words at other drivers, glaring at the service desk person whose computer is running slow, and getting a bit short with the waiter because your mind is racing: What if this client thinks I’m ignoring her? What if my colleague thinks I didn’t respond because I don’t care and moves forward without my input? What if this prospect moves onto someone else because I seem inaccessible?

In all of these situations, simply putting up an out-of-office responder could prevent much of the stress and pressure caused by worrying about what others are thinking.

Another way you can sabotage your attempts to have any real downtime is to proactively look out for work emergencies. This can lead to you compulsively check your phone during the times when you’re supposed to be off. And even when you’re not actively scanning your inbox for trouble, you’re thinking about whether you should be.

For any days where you’re not working the full day, have a designated person who can field most items and contact you if a true emergency comes up. Prep them on exactly when you want to be contacted. For example, Always contact me if anything comes through from the client for the upcoming trial; otherwise only contact me if it’s a high-stakes, urgent issue. Include your point person’s name and contact information in your autoresponder.

Don’t forget to tell them how you want to be contacted, too. I recommend staying out of email or other messaging channels unless it’s your designated work time, so ask your point person to contact you via a text or phone call if you need to go check your inbox. That way you won’t be on a hike and tripping over roots in an attempt to scan your inbox or feeling guilty about just staring out into the horizon at the ocean.

A real key to unwinding is knowing that everything will be okay until you re-engage — and that if it’s not, you’ll be contacted about it.

It can work to set up formal meetings if you plan to work all morning or a full day and know you’ll have a set place with consistent internet access. But you’re setting yourself up for potential drama if you commit to specific times in the middle of the day or in the evening.

When you’re traveling, you may think you know how things will go, but you don’t really know. A boat cruise you thought would be done by 2 PM might not dock until 2:45 PM. — and now you’re scrambling to see if you can take the meeting from your rental car. Or maybe you thought your family would be spending the day at the hotel pool and it would be no problem to pop up to the room for a quick meeting at noon, but then they decide they want to go to the beach instead. Now you’re faced with the choice of missing out on a substantial amount of family time on a day you had intended to be off or having to reschedule the meeting.

Whenever possible, keep communication message-based and asynchronous. If you must do a call, try to keep it informal — think I’ll call you sometime today instead of I’ll call you at 1 PM.

To have space in your schedule to relax, you need to do less than you would if you were in the office. If you’re traveling but still doing some work, it’s tempting to answer a random question, help someone out, or otherwise participate in non-urgent work items “real quick.” But if you want to feel like you took some real time off, you can’t engage in everything you typically would in the office.

When your out-of-office is on and your point person is on duty, you’ll need to resist the urge to even open messages that aren’t related to your urgent, must-do items. If you open them, you’ll either feel compelled to respond or be thinking about your answer in the background while you’re trying to relax and unwind.

Leaving your on-vacation working hours undefined is one of the quickest ways to undermine your attempts to be both productive and relaxed. Imagine that on one day of your trip, you’d like to sleep in a bit and enjoy a leisurely breakfast before starting work. But that might mean you’re not starting until 10:30 PM, then when you’re done at 2 PM, you feel like you lost a whole day of your vacation. Even though you only technically worked three and a half hours, it felt like a lot longer.

To the extent that you can, determine your work start and stop times in advance (for your own sake and those traveling with you). I recommend frontloading any longer stretches of work while you have momentum from having just left the office, then tapering down so you feel like you can get more and more relaxed throughout your travels. For example, maybe you decide the first full day of your trip, you’ll work from 12 PM to 5 PM and go out with your traveling companions for dinner. Then for the rest of the days, you’ll do a review of any urgent matters from 8 AM to 9:30 AM and then be off for the rest of the day except for a quick check-in before dinner.

Although working during vacation isn’t ideal, it is possible to get critical work done while enjoying some refreshing time off. The key is to do a little pre-planning, making sure to avoid a few common mistakes people make when mixing business and personal travel.

Elizabeth Grace Saunders is a time management coach and the founder of Real Life E Time Coaching & Speaking. She is the author of How to Invest Your Time Like Money and Divine Time Management. Find out more at RealLifeE.com.