Four Tips for an International Workation

Chicago winters, to put it as lightly as I possibly can, suck. The gray skies roll in, and like the temperatures outside, Vitamin D levels hit an all-time low. I usually get a little restless as the city plows through its “fools spring” at the end of February before bracing for March’s inevitable second or third round of winter. This year was no different. But since 18 Coffees is a remote-first organization, I decided to pack my bags and take work-from-home to the next level by spending two weeks on a Caribbean island.

While I’ll happily tell you every little detail about the non-work parts of my trip, a few things about my international “workation” stood out to me and might help those of you thinking of doing the same. So whether you’re considering a temporary move, a few days away, or a two-week stint like mine, keep these things in mind when planning to work somewhere besides your home.

1. Set expectationsIf you go on a workation, know it will be just that — a combination of work and vacation. You likely won’t have the luxury of seeing every sight, taking every tour, or experiencing everything your workation destination offers in the same way you would on a typical vacation. When working remotely, you’re most likely still dedicating the full eight hours of your standard work day that you would back home. You probably just have a better view. As long as you level-set expectations for your trip and are flexible with your schedule as work needs arise, you’ll be in great shape.
2. Note the time differenceA primary reason I chose the Caribbean was the time zone. Working from Europe for an extended period of time sounds fantastic, but if you’re US-based and locked into a certain timezone, it might not be the most feasible option. With the rest of the 18 Coffees team based in Chicago, being two hours ahead was ideal — I was able to get up early, enjoy morning adventures, and then settle into work for the day.
3. Align your scheduleYour company’s busy season probably won’t be the best window to work remotely. You never know what wifi connectivity issues could come up, what coffee shops will be too loud to take calls, or what last-minute needs might arise that might require close proximity to a computer. And if you’re working 10 hours instead of your usual eight, you’ll lose daylight hours to explore your destination. My recommendation: Travel during your organization’s off-season instead.
4. Use your PTOMy two-week workation was incredible — it gave me time to experience my destination, work full eight-hour days, and come home with a sunkissed glow. I took one personal day off and made full use of a paid company holiday. That said, a part of me wishes that I would have had the foresight to use a little more PTO to take a few more adventures and fully appreciate the relaxing part of the workation.