“Workcation?” my friend said incredulously. “What the heck is that?”

I thought a workcation was a commonly known phenomenon in the career world. But turns out, it’s something that few know about (and that my boss and I may or may not have made up).

But here we were, each spending a week working remotely from other places. We still click-clacked away on our laptops for approximately eight hours a day. We still answered emails, were still available on our company chat system, and still attended meetings via video hangout.

We just did it from a patio in the Dominican Republic and a cool cafe in Washington, DC instead of our office in New York.

Now, let me answer the next question I always got when talking about what I was doing: “Why not just take an actual vacation?”

I understand the question (and the incredulous tone that usually comes with it), but let’s be clear—I’m not advocating workcations in lieu of actual vacations. Rather, I’m advocating them in addition to your real time off. Taking a workcation gives you a chance to get a change of scenery, without using your precious vacation days. You still get to enjoy a fun new place or spend time with far-off loved ones during your nights and weekends (and lunches), but you don’t have to deal with the stress of preparing for, missing, and recovering from a week off of work.

Alright, I hear you: “Sounds great, but how can I really make this happen?” If you’re ready to live your workcation dreams, read on to learn how to get it okayed by your boss, how to set yourself up for success, and how to really enjoy your time away from the office.


Choose Your ’Cation

Choosing the perfect place for a workcation is a little different than choosing one for an actual vacation. Ideally, you want to go somewhere where you won’t be upset that you don’t have your days to explore. In other words, avoid places where there’s a ton you want to do or where the main attractions happen during the day.

Better options for workcations? Cities where you used to live (you won’t want to tour around too much, but will have plenty of time to visit with family or friends in your off hours), relaxing destinations with Wi-Fi all around (think resorts where you could feasibly sit by the pool and work), or destinations where you don’t care too much about site-seeing but just want to get a feel for the place (I recently did this in London, and was able to get my few top attractions in on the weekend, and then just enjoy eating out and hanging out in pubs during the week after work).

In other words, save the African safari or the trip around Southeast Asia for your actual vacation, and go somewhere a little more low-key for this trip.


Ask Your Boss

I understand how it could be easy to think that most bosses won’t be down with this idea. And in some companies or with some roles, it won’t be feasible. But with a good deal of work increasingly done remotely, asking for a workcation should become easier and easier.

The key is to first acknowledge that it’s a bit of a strange request, and then show why it would not only be better for you, but ultimately a bonus for the company by keeping you happy and productive.

Try something along these lines: I know this is sort of strange and might not be feasible, I was wondering if I could work remotely for a week this summer.

Then, go on to explain the circumstances:

I think being out of the office would help me clear my head and help me work on [insert big project].

Or:

I’d like to be with my family this week and would rather continue working so as not to leave the company hanging or let [insert project] stagnate.

At this point, you should also be prepared to talk through some of the logistics of how this will work. You can talk specifics closer to the actual date, but explain about how many hours a day you’ll plan on checking in, how you’ll stay in touch, and what work your boss can still count on you to do.

Still unsure? Take some pointers from Elizabeth Lowman’s advice for asking your boss to work remotely—the situation is slightly different, but the advice still holds true!


Get Prepped

As your workcation gets closer, it’s time to really come up with a plan for how the week will play out. There are a couple of things to consider and talk to your boss about:

  • Be very clear about when you will be working—and when you won’t be—so your boss and team know exactly what to expect.
  • To that end, if you are going to want a day or an afternoon or two off during your time away, try and work that out as early on as possible.
  • Discuss how you can be reached while you are away. Will you be available over chat? How often will you be checking email? If people have an urgent request, how should they contact you? If something happens and you can’t be reached, who should have decision power instead?
  • Decide which meetings you’ll be able or expected to attend while you’re away, and plan for how you’ll join in on them.
  • If there’s any work you’ll need to pass off for any reason, make a plan for that.


Be Productive—and Have Fun!

You’ve planned, you’ve jetted off, and now it’s time to have a little fun (while staying productive, of course)! There are a couple things I’ve found helpful for having a rejuvenating and fun time—and still getting my work done.

First, just as you were clear with you boss and team about when you would be working, be clear with yourself and any friends you’re visiting or traveling with. It can be far too easy to fall into the trap of either working too many hours in order to prove that you’re still being productive, or not working enough because you say yes to every friend who asks if you want to meet up for breakfast or start drinking at 3 PM. Understand when you’re working (and when you’re stopping), and be firm about it.

That being said, don’t be afraid to take some breaks during the day to enjoy yourself. I’ll often get up on the earlier side, bang out a chunk of work in the morning, and then take an actual lunch break (no sad desk salads allowed on workcation) to meet up with someone, take a yoga class, or do a little exploring of a new neighborhood.

Finally, make sure to change locations! Nothing’s worse than traveling somewhere fun and then spending the bulk of your time sitting in your hotel room in front of your computer. So, switch it up! Go work out on the balcony or by the pool. Find a coffee shop in a different neighborhood each day to work from. One day from London, I even worked from a fancy hotel lounge while enjoying afternoon tea! As long as you have access to Wi-Fi (do thorough research on this before heading out—nothing is worse than scrambling to find internet in an unfamiliar place) and a quiet enough place to take any calls or meetings, you can still get your work done while enjoying what your destination has to offer.



It may seem like a workcation wouldn’t be very relaxing, but I always come back refreshed and ready to work even harder than I had before (and without the post-vacation inbox). So give it a chance—it might surprise you.


Photo of woman working on beach courtesy of Shutterstock.