What is Workationing? The New Digital Nomad Trend

Definition of Workationing:

Workationing, (verb) – methodically bouncing around to different locations around the world, working along the way. Ideally, you stay in one place long enough to get a feel for the local flavor, and get a specific work project done.

Workation, (noun) – a working vacation, where you go to an exotic location and complete specific tasks or accomplish a goal before you leave. In between work sprints, you vacation.

Workationing isn’t about taking a vacation from work. Workationing is about fully immersing yourself in your work while also building in ways to pamper yourself and unwind so you can be even more effective and productive.

The Four Rules of Workationing:

1.) You must make more money than you spend. In order for workationing to be a consistent part of your life, you need to make more money on the road than you spend. This is easier than you think, especially in foreign countries, as long as you’ve got one of those work from anywhere jobs.

2.) You must travel light (carry-on + personal item). You might not think that you can travel for 6+ weeks with just a carry on and personal item, but you can – even if you’ve got a blow dryer, curling iron and three pairs of shoes. All that stuff, when smartly packed, can fit into a small suitcase. If you’re going to become a digital nomad you need to get comfortable with traveling light, because the alternative sometimes means carrying a 50-lb suitcase to a 6th-floor walkup. If a taxi drops you off at the wrong place, you don’t want to have to lug a giant bag around for miles. Plus, large suitcases cost A LOT more money when you’re hopping cheap flights throughout Europe.

3.) You must focus on, and stay in one place long enough to accomplish a goal. This is an important point, because if you’re traveling somewhere new every 3-7 days, you A) can’t fully take in the area and work B) you’ll be drained from the constant travel C) that last point makes it really difficult to do good work. 2-6 weeks is ideal for workationing, and if you’re not accomplishing a specific work task or goal by the time you leave, you didn’t have a workation…you had a vacation.

4.) Road karma is a thing, and you should always keep it positive. If you’ve spent any time traveling, you know about road karma. It costs you nothing at all to be friendly to the people you meet along your journey, and that free kindness can pay dividends as you travel. Road karma is real, and you should learn it, love it and live it.

Workationing: working abroad


The #1 Requirement: You Must Be Able To Work From Anywhere in the World

Before you can become a digital nomad workationer, you need to untether your life in a way that accommodates extensive travel. First, you need a job that enables you to make money from anywhere. These types of jobs can include freelance writing, website development, affiliate marketing, tech stuff, and any other job that you can do remotely. Once you can work from anywhere in the world, you can work from everywhere.

If you’re hoping to find a local job once you get to your destination, you might be a nomad but you’re not a workationer. All workationers are digital nomads, but not all digital nomads are workationers. For you visual learners, here’s what that Venn diagram looks like:


If you’ve got a 9-5 job that requires you to go into an office every day, you’re not going to be able to workation (with rare exceptions, like if you save up money and vacation time to travel somewhere and workation to write a book). Until you can work from anywhere, you’ll be tethered to wherever you happen to live.

If becoming a digital nomad appeals to you, you’re going to have to figure out how to ditch your cubicle and find another job that enables you to work from anywhere. Craigslist is usually a good place to start, and you’ll probably want to stay within +/- 6 hours from where your clients or employers are. Although Bali is cheap and beautiful, it’s also 12 hours ahead from EST – and that can make working abroad more difficult than it needs to be.

Despite what many digital nomad bloggers will tell you, most clients and employers care about the hours that you’re available, and it does them no good if you’re only on the clock while they’re sleeping.

Workation: work from anywhere

Untethering Your Life, So Becoming a Digital Nomad Becomes Profitable

Once you’ve found a job that lets you work from anywhere in the world, you’re going to need to figure out what to do with your stuff. Who’s going to take your cat? Do you have a lease? Can you get out of it? Or do you want to keep your current home – and the ongoing expense that comes along with it – for when you return? These are the types of questions that you’re going to have to ask yourself, and the answers are different for each person.

The goal with untethering your life is to reduce your monthly expenses “back home” so that you have more money on the road (or don’t need to make as much money on the road). You’ll probably need to put some stuff in storage, and once you close the door on that locker you’ll finally be free to take the next step: getting on a plane and going somewhere fabulous. You go, you workationing digital nomad!

How Workationing is Different Than Being a Digital Nomad

The term “digital nomad” actually comes from a book of the same name that was published in 1997. The authors, Tsugio Makimoto and David Manners, coined the term to refer to what they predicted would be an emerging trend in the coming years — namely, people choosing to live a more nomadic lifestyle as technology continues to make many jobs less tethered to a specific location.

It turns out that this prediction was right on the money, and the term was adopted by many of the the new generation of entrepreneurs, designers, marketers and more who decided to take advantage of their ability to work from anywhere in the world.

Workation: working abroad

While “digital nomad” refers broadly to this kind of untethered, “work from anywhere” lifestyle, it also easily embodies the not-so-great aspects and pitfalls of working and traveling abroad that workationing is specifically designed to eliminate. Specifically:

Digital Nomads Are Wandering Aimlessly

Not to Webster’s Dictionary you, but a lot of the problems with the digital nomad lifestyle can be found right in the definition of the word “nomad.” The word can refer to “a wanderer or itinerant” or to a group of people who move about from place to place following seasons or trade routes — and there are a couple of reasons why that term is problematic.

First of all, whether you are a business owner, a freelancer or just someone lucky enough to have a 9-to-5 that doesn’t keep you chained to a cubicle, you probably know that “wandering” and mindlessly following routes that other people have already established is no way to get ahead in business. You need to set goals and aggressively pursue them in order to get where you’re going. Your typical digital nomad is much more like an explorer or a pirate on the high seas than a bunch of dusty people following around a herd of buffalo.

Secondly, the “nomad” part of digital nomad also flies in the face of everything that the work from anywhere lifestyle stands for. From the logistics of travel to the emotional work of making such a massive life change, it’s not easy to untether your life and set off into the unknown. People who choose to do so aren’t wandering — they’re choosing to live very intentionally.


The #workation is coming to an end, and now I’m ready to get back to the grind. #hustlehard #treplife

A video posted by Kari D. (@karidephillips) on

Digital Nomads Have To Be Willing to Rough It

Listen: there’s no denying that it takes a special level of badassery to rough it on the road. Run a quick Google search for “digital nomads” and you’ll find a host of blogs written by people who decided to hit the road first and figure out the logistics second — and that is not an easy path to take.

From sleeping in sketchy hostels to finding day labor in the jungle when you run out of money to braving more gastrointestinal distress in a year than most people encounter in a lifetime, adopting a nomadic lifestyle without a solid plan for how you’ll make it all work can be rough — and it’s not for everybody.

Workationing is based on the premise that there is a better way. It’s all about setting yourself up before you leave with a steady income, knowing (and religiously sticking to) your budget and ensuring that you always make more than you spend so that you never find yourself in a scary situation without the means to get out of it. And with the right planning, you absolutely can ensure all of those things.

Beyond just avoiding the more unpleasant (and dangerous) aspects of the digital nomad lifestyle, workationing is about actively seeking out the kind of luxury, relaxation and adventure that you’d associate with a really great vacation. You’re going to be working hard on your workation, and when it’s time to power down for the day there is nothing better than being able to head to the beach, enjoy an amazing dinner or even take the opportunity to check off some items from your bucket list. If you can make that happen, why would you want to do it any other way?

What About Those Work Abroad Programs?

Over the last couple of years, as the digital nomad movement has really started to take off, work abroad programs have started to spring up all over the place. These work abroad programs (Remote Year, We Roam and others) allow aspiring digital nomads to sign up for a pre-planned journey to multiple countries usually lasting 6 months to a year with 50+ other people.

Workation: we work remotely

The interest level in these programs has generally been pretty high — which makes sense. Work abroad programs provide an easy answer to a lot of the logistical issues and anxieties that prevent people from taking the plunge into the digital nomad lifestyle. First of all, knowing that someone else will be handling your itinerary from lodging to flights to outside excursions can feel like major weight off your shoulders. Also, having a cohort of friends and colleagues to go on this journey with you makes leaving the comfort of your family, friends and co-workers behind seem a lot less scary.

However, as the reviews from people who participated in these travel abroad programs have started to roll in, it’s become obvious that delivering on the promise of a seamless working abroad experience for that large of a group is difficult (if not utterly impossible). Some of the most common complaints in reviews about work abroad programs include:

  • Sketchy accommodations. While there are endless deals for smaller groups seeking luxe lodgings and workspace overseas, the logistics of finding affordable options for 50+ people who are all expecting to have a more or less comparable experience is tough. And unfortunately the result is that these groups often find themselves being put up in windowless basement hostels or unsafe neighborhoods.
  • Sky-high prices. Remote Year charges a $5,000 down payment, plus $2,000 per month for their program which includes airfare between destinations, lodging and workspace. What it doesn’t include is airfare to and from your journey, food and any excursions or activities — all of which you will pay for yourself. (Just for reference, you could book a baller Airbnb with a pool (like this one, this one, or this one) for less than $2,000 a month and split it with a few roommates.)
  • An Inauthentic Experience. While it can help ease your initial jitters to know that you’ll be traveling with a large group, rolling up on a quaint restaurant in a seaside town with 50 of your new best friends is not exactly the best way to ingratiate yourself to the local people or to get an authentic traveling experience. To really get to know a new place, you need to be willing to lose yourself in it a little bit, which is basically impossible to do with such a large group.

For us, when it comes to the decision between workationing and adopting a more traditional digital nomad lifestyle, it’s a no-brainer. Workationing provides the lifestyle that we want at a price we can afford, while still putting our work front and center. Under those circumstances, all we can do is win.

Our journey is just beginning. If you’re interested in our story and what happens as we travel the world while working and having adventures, check out The Workationing Podcast (be sure to subscribe to automatically get new episodes). If you don’t have iTunes, you can find us over at SoundCloud

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