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Taming Your Post-Vacation To-Do List

image for Bacho/Shutterstock

With summer just around the corner, many employees and managers find themselves taking vacation or celebrating holidays without thinking about work. This is great for morale and a necessary recharge for most, but what happens when you return from vacation?

Some people return to hundreds of unread emails, dozens of unaccomplished tasks and the to-do list from hell. What started as an enjoyable time away from the office ends with skyrocketing stress levels and a sense of dread. While there might not be a perfect fix for taming the post-vacation to-do list, there are a few strategies you can employ to make sure your first few post-vacation workdays are manageable.

"Nothing wipes out that post-vacation glow faster than a packed inbox and an endless to-do list upon your return," said Gemma Roberts, who runs The Work Life Blend, a site devoted to finding a better work-life balance. "It leaves you asking what's the point if you end up coming back to even more work than before you left."

We spoke to business professionals, like Roberts, about their best tips and tricks for both preparing to take a vacation and eventually catching up after the vacation. [Related: 6 Tech Gadgets for Your Working Vacation]

"If you want to minimize your to-do list and feelings of stress, preparation is key," Roberts said. "Start by managing expectations prior to your holiday."

Many workers have found themselves in that pre-vacation scramble to get as much done as they can in the day or two leading up to their trips. Maura Thomas, an attention-management expert and author of Personal Productivity Secrets (Wiley, 2012), recommends prepping your out-of-office work a week in advance and contacting the appropriate colleagues to make arrangements for your time away.

"If you're heavily involved in a project or working extensively with a particular team, let them know you'll be on the road, even if you still plan to work," said Thomas. "Request that they hold anything that isn't urgent until you get back. This will minimize your backlog."

For voicemail messages and automatic email replies, schedule your official "away" dates for one day before and one day after your actual trip. If your contacts expect a delay, it relieves some of the pressure to answer them immediately before you leave or upon your return. You may well end up answering those messages earlier, but it's always better to under-promise and over-deliver, Thomas said.

Getting ahead of the post-vacation to-do list is critical. If you enter vacation behind on work, you'll return from your trip with an intimidating to-do list. The best way to prevent this is by preparing thoroughly before taking time off.

Don't leave preparation efforts until the day before you leave for vacation. Start preparing days, or even a week, in advance of your trip. This limits stress during the preparation process and ensures that you'll be fine going back to work after your vacation. 

"Make sure you give your colleagues as much notice of your vacation as possible and remind your manager," Roberts said. "That way, your workload can be managed. Discuss with your manager whether it would be possible to delegate certain tasks to other team members. Cross-training within teams is always a good idea in order to minimize the risk of dependency on one employee. This not only helps when someone takes a vacation but also helps to cover periods of sickness and staff turnover."

"Before you take off, block out time on your calendar for the morning of your return," said Justin Hale, speaker, training designer and master trainer at VitalSmarts. "Then use that time to get up to speed. Now, this does not mean you do all the work in front of you. The purpose of this time is not to work, but to get clear on your work."

Don't schedule a handful of meetings for your first day back from vacation, at least not early in the day. While it may help you understand what you missed, it's best to spend a good portion of the first day working through and planning your to-do list. If you wait to organize your work and push off responsibilities, you may find yourself even more stressed out two or three days after you've returned. That being said, you don't want to overdo it your first day back.

"I think it's a fairly common mistake to expect yourself to be able to accomplish everything on your to-do list at the drop of a hat upon returning from a vacation," said Deborah Sweeney, CEO of MyCorporation. "Give yourself as much breathing room as possible to readjust. I would advise accomplishing as much on your to-do list [as possible] before you leave for vacation so the list is a little bit easier to tackle upon return. Organize your to-do list by order of importance and work your way through each item accordingly by doing a little bit each day until you're gradually back in the swing of things."

Preparation matters, and it's important to create a plan that allows you a manageable first day back at work. This means limiting meetings, if possible, to allow time to work through your to-do list. This doesn't mean you'll finish everything in one day, though. If it takes you an extra day or two to efficiently cross items off your list, that's OK.

One of the better ways to limit your stress on the first day back from vacation is to break down your to-do list, according to Vivian Young, senior content manager at Website Greenlight.

"Split it into three sections: to do today and tomorrow, to do by the end of the week, and to do whenever," she said. "Limit the amount of items on the first list. Too much too soon doesn't make for a productive first day back on the job. Include at least two things that are easily accomplished – like undo your 'away' messages on your voicemail and email and look over unopened mail or documents on your desk."

A strategy like this makes it easier to feel comfortable during the process of catching up on work. Sorting tasks into to-do lists for later in the week can make your first day back feel less daunting.

One of the most dreaded post-vacation tasks is going through the hundreds of emails received while away. You can quickly catch up on your overflowing inbox with what Thomas calls the "four-pass process."

  • First pass: Sort by subject. For multiple messages with the same subject line, delete everything but the most recent one, and then, after taking all your "passes," read that one from the bottom up. This will likely eliminate dozens of messages in just a minute or two.
  • Second pass: Sort by sender. This will allow you to quickly delete or file the newsletters, coupons, advertising and any other mail that isn't from an actual person.
  • Third pass: Sort by date received. Work from the oldest to the newest. This may be contrary to how you usually view your messages (newest to oldest), but when you've been out, think about who's been waiting the longest for a reply.
  • Fourth pass: Respond. When processing what's left, resist the urge to "skim and skip." It's important to deal with each message, because it won't get any easier if you leave the message there to read again later. If there's anything you truly can't handle now, move it to your task list for later completion.

Creating a schedule for before, during and after your trip – and sticking to it – will give you the peace of mind you need to truly enjoy your time out of the office and come back feeling refreshed instead of stressed.

"Catching up on that backlog is a lot easier and less stressful if you actually plan for it," Thomas said.

Additional reporting by Nicole Fallon. Some source interviews were conducted for a previous version of this article.

Bennett Conlin

Bennett is a B2B editorial assistant based in New York City. He graduated from James Madison University in 2018 with a degree in business management. During his time in Harrisonburg he worked extensively with The Breeze, JMU’s student-run newspaper. Bennett also worked at the Shenandoah Valley SBDC, where he helped small businesses with a variety of needs ranging from social media marketing to business plan writing.