How to Work on Vacation Without Hating Life

Vacations are supposed to be a time to get away and forget about work for a while, but let’s be real – sometimes the only way to get away is to take some of the work with you. You’re in the middle of a project, you’re the crucial decision maker or there’s just too much to do. It’s a challenge for whether you work in a central office or do remote work.

Working on vacation adds an extra level of complication and requires compromise. You won’t be able to do as many activities or relax as much. You have an extra layer of logistics being away from your desk and supplies. But don’t despair. It’s extreme remote work. But it can be done in a way that allows you to get things done and have time for fun without ruining everyone else’s vacation.

Set expectations and make a plan          

The first step in setting up a successful vacation with work on the side is to set the right expectations – yours, your colleagues and your family. Be realistic about what you can and can’t accomplish. This isn’t the time to load up your to-do list in hopes that taking on more than you can handle will make it happen. That just leads to frustration and disappointment for you and your colleagues. Let those at work know what you expect to accomplish so they can adjust. Your family should also know what will happen. There are times when you won’t be available but there will be lots of time when you are.

Next, figure out what work you want to do and then prioritize. Determine what absolutely has to get done and what could be pushed off if necessary. This is not a time to be an overachiever – you’re already doing that by taking your work with you. Estimate the time you will need and build it into your day. As you make your plan, consider your logistics. What can you get done if the WIFI isn’t working? What can you get done if you don’t have access to a phone?

Get ready before you leave

Figure out what supplies you will need and think about having backups. Do you need a computer, tablet, reports, pens, or paper? Where you will pack them and what are you going to do in the hopefully unlikely event that they get left or lost? Do you need to send files to someone who can send them to you or store them on the cloud where you can access from anywhere?

Do some investigation on the set up where you are headed. Are you going to need WIFI and will you be able to find it? Is there mobile phone service? Will you have access to a landline if you need it? Taking a little time to look into it and prepare before you go could save you hours of angst later.


Before you go, talk extensively with your colleagues to make sure everything is set up. Let them know what you expect to accomplish and when you will or won’t be available. Once you’ve left, however, limit the communication as much as possible. Check in to email only at a certain time or set up times for phone calls. It’s a nice concept to be available whenever, but it’s awful when you miss the whale jumping out of the water because you’re answering a call.

Share your plans with those with whom you are traveling. Let them know when you will be available and when you won’t. Take into consideration their preferences. Don’t discount their desire and need to spend time with you.

Set the schedule but be flexible

Determine how much time you want to dedicate to work and figure out when in the day it should happen. Some people prefer to get up early and get things out of the way before everyone gets up. But maybe early afternoon after lunch when everyone else is resting is better. Or, perhaps after everyone is going to bed. Note the theme – you are working while everyone else is resting. Just as important as scheduling the work time is scheduling the fun time. Set aside time for pure vacationing. Make plans to go on tours, sit by the pool or wander the streets. It doesn’t matter what you do so long as it isn’t work.

As much as it’s nice to stick to a schedule, it may not be possible. Opportunities come up. Tours fall through. A crisis may happen. Be prepared to make changes as necessary. Focus on the most urgent tasks and do the rest later.

Suggestions from working vacationers:

  • Set a timer and stick to it. Get done what you can and enjoy the rest of the day.
  • Separate work and fun as much as possible. It’s tempting to take business calls while waiting in endless lines at Disney World, but you miss out on conversations with your kids.
  • Don’t take on a major project. Tackle little stuff you can do early or late when the family is asleep.
  • Schedule family time as well as work time and negotiate it up front so there are no surprises and there is a plan in place for each phase.
  • Remove yourself from the fray. Working requires some concentration and you can’t expect your family to contain themselves when they are on vacation. Be the one who goes off to some quiet corner to do your business and come back when you’re ready to play.

Photo by Patricia Prudente