7 Ways To Take A Workcation and Be Productive

Masthead Media Company
Don't Panic, Just Hire
4 min readJul 21, 2016

When was the last time you took a totally unplugged, get-away-from-it-all vacation? Chances are, it was before you started working for your toughest boss of all: Yourself. Many business owners (if not all) are still answering emails or managing staff while ostensibly lounging on a beach or hiking the backcountry.

It’s just reality: Many of us feel more stressed trying to completely ignore our businesses than checking in periodically or answering an email or two. That’s why my Masthead Media co-founder Julie Ilkovich and I have wholeheartedly embraced the concept of “workcations”: a style of travel that enables us to focus on work when needed and then go totally off the grid — during the same trip and, very often, even in the same day.

Some workcations are as short as a long weekend; others can be several weeks. My partner Julie once worked remotely from a beach in Belize for nearly two months, and our editorial marketing company continued to thrive during that period.

While it’s still very important to take a few completely uninterrupted days off, planning a workcation in a dream locale can often be just as liberating and reinvigorating for your entrepreneurial soul. Plan and execute it right, and you may just make “unlimited workcation days” your next company perk. These seven tips will get you started.

1. Kick it Off With a Few Days of Downtime

The best way to start your workcation is with an actual vacation. Two or three days on your own will give you a chance to relax, and will let you check off some “must do” activities that you won’t have time for while you are working. As with any vacation, plan this workcation around slower time at the office to set yourself up for a stress-less getaway.

2. Be Mindful of Time Zones

If you’re traveling to the other side of the world, consider how the time change will affect your workday — and therefore your free time. Extended workcations — working full days in a remote location for a few weeks or more — tend to work best when you’re within a few hours of your office and/or clients. If you’re not planning to be fully available — just answering emails periodically — you can pull off a workcation in a far-flung place like Thailand or Australia.

3. Choose Your Accommodations Wisely

Sure, that boutique hotel is right on the beach and has an incredible pool deck, but the real question is, how fast is the WiFi? Whether you’re staying at a hotel, guesthouse or AirBnB rental, high-speed Internet access and ample workspace are non-negotiable. Vet these factors with staff, hosts, and even other guests through online reviews.

4. Manage Expectations

A workcation is still a new travel trend, and one some client and other business contacts may not entirely understand. Provided your work hours and accessibility stay the same as usual, explain that you are simply working remotely for a set period of time. Communicate any logistic differences — such as reaching you via Skype as opposed to cell phone — in advance to prevent frustrations on both sides while you are away.

5. Map Your Challenges

Take the time to plot out potential challenges so you don’t have to deal with them for the first time on your trip. A few things to consider: There is a brand-new set of potential distractions in your office paradise — how will you plan to avoid each one? Your remote office won’t have all the resources of your home office — what can you do to prepare for this? There will be days where you feel like you’re not experiencing enough local culture because of work responsibilities — how will you balance that? Asking yourself these questions and creating a thorough game plan are among the keys for a successful trip.

6. Define Your Workday

This strategy may be the hardest for those of us that are on the entrepreneur schedule — as in, round the clock. Defining set hours for your workday will help you keep your workcation from becoming too much work or too much vacation. Once your business hours are in place, you can schedule guilt-free time to relax. Enjoy morning swims, lunch breaks at new restaurants, and weekend excursions that don’t cut into your workday.

7. Take It Easy

If you’re the kind of traveler who usually squeezes in as many destinations as possible on one trip, you’ll want to adjust your itinerary: workcations are not conducive to destination hopping. You’ll want to explore every new place you visit, which cuts into your ability to stick to your work hours. Your life will be easier — and it will be easier to keep work as a priority — if you make your workcation a single destination trip.

If you’ve taken a workcation, what strategies worked best for you? Feel free to share in the comments below!

Written by Amanda Pressner Kreuser.

Originally published on Inc.com on April 13, 2016.

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Masthead Media Company
Don't Panic, Just Hire

Masthead Media is a full-service media company creating editorial-quality content, digital strategies, and influencer programs customized for brands.