How to Structure a Remote Year (Successfully)

Sarah Ramsey Updated on February 29, 2020

remote year

Traveling from exotic place to exotic place, working with different groups of interesting people, getting those creative juices flowing while surfing in the morning, and eating amazing street food at night. Ah, the glamorous life of a digital nomad engaged in a remote year!

But with that glamorous lifestyle comes figuring out a new public transportation system every month, finding a comfortable, safe place to sleep and do laundry, and setting up an office with solid WiFi in an unfamiliar country.

More and more people are choosing to be digital nomads, which the Urban Dictionary defines as: “One who derives income remotely and online, rather than from commuting to an office. This enables the digital nomad to not need a permanent home base, and she/he can travel anywhere at any time. Often find them couchsurfing, living in hostels, with friends, or in third world countries where rent is cheap.”

As being a digital nomad becomes more commonplace, it gets both easier and more complex to figure out how to jump in yourself. On the one hand, have computer, will travel: just do it, right?

But if you need a little more structure to your nomadic ways, a remote year might be a good option for you.

What Is a Remote Year?

A remote year is a combined life- and work-style in which a digital nomad lives and works for short periods of time in a series of locations. They may work as a freelancer, as an entrepreneur, or for a company back home, and generally work from co-working spaces or other alternate workplaces.

It’s different than a really long vacation, because while you have the opportunity to see and experience the world, it’s mostly about the work you’re doing. You might be lucky enough to work full-time for an organization that is comfortable with remote teams, you might be an entrepreneur with your own start-up, or you might be a freelancer working for multiple clients with no tie to one location.

Some of the benefits of doing a remote year are:

  • Seeing new places and meeting new people
  • Gaining exposure to new ideas and creative solutions
  • Having the flexibility to vacation while working, or work while on vacation
  • Building an entirely different type of community

But as with anything, there are a few downsides:

  • Finding a place to work
  • Finding a place to live
  • Working on a different schedule than your team at home
  • Being separated from your team
  • Being separated from your family and friends
  • Not having a place to call your own

If you’ve decided to do a remote year, what’s the best way to structure it, how do you get ready for it, and when do you come home? Let’s talk about the ways you can make a remote year awesome and productive, while avoiding some of the pitfalls common to constantly working on the road.

What’s the Best Way to Structure a Remote Year?

Like any kind of trip planning, to structure your remote year you can rely on existing organized programs or you can do it on your own.

There are several organizations that will put you with a group of like-minded people and deal with all the arrangements for transportation, lodging, and workspace for the whole.

If you’re not a planner, or you want to live and work in a part of the world where you don’t speak the language and have no working knowledge of the cities or culture, this might be a good option.

These programs also give you a ready-made cohort. They are people you can bounce ideas off of, go to dinner with, and be your backup and support system when the inevitable transportation or lodging nightmare happens (being stuck overnight in an airport in a city where you don’t speak the language is a lot less scary when there are 30 of you instead of you alone).

To be fair, it also sounds a little like The Real World meets a 12-cities-in-seven-days grand tour, but if that’s your thing, an organized program could be the way to go.

If you’d rather do things on your own, here are a few tips and things to consider.

Decide how often you want to move and where you want to go. Many of the organized programs are set up so that you move each month, but planning things yourself means you get to decide what frequency of change you’re comfortable with.

You also get to decide if you want to stay in one part of the world, or hit as many different continents as you can.

One benefit to planning your own year is that you have the flexibility to change your plan at any time. Depending on your comfort level, you can fix your logistics in place for the entire year or for the first three to six months, and then update as you go along.

If you’ve never traveled extensively before, going someplace unfamiliar can be a shock to the system. If you’re considering doing a remote year, that freshness is probably what you’re looking for, but don’t underestimate the toll it can take on you.

I remember stumbling on a local Mexican taqueria in Budapest (no, seriously; it was as good as my favorite Mexican place back home, with great salsa and good margaritas) during my brief stop there after two weeks traveling through Croatia. While I loved Croatia, and Croatian food and wine, most of all, finding this little bit of comfort food was a break from the unfamiliar that I desperately needed.

So, you might build in some flexibility to find a bit of the familiar or to give yourself time to adjust to the nomadic lifestyle.

If you don’t plan things out completely in advance, my advice would be to at least focus on two or three steps ahead. Have your next move confirmed, but also be working on plans for the following two. It takes time to research and set things up, especially if you have language barriers to work around. The last thing you want to do is be heading for the airport while at the same time emailing your next lodging host to see if you have a place to sleep that night.

You can stay flexible and still go through organized programs that provide lodging and workspaces. Here’s a good link with many different short- and long-term options. If you don’t want to do the whole year completely structured, you might, for example, do a four-month program as a way to get used to the lifestyle, then figure the rest of the year out on your own.

Regardless of how you set things up, here’s a piece of advice: book your lodging in advance. If you’re backpacking across Europe, you might be okay relying on a network of hostels that you book as you arrive in town. But remote years are about working, and you want to find a place where you can spend at least a month, so perform due diligence on your living arrangements.

Of course, you can book a room or apartment through Airbnb, but you can also find co-living spaces in many cities around the world. To start searching for your perfect location, look here, here, and here.

Some co-living spaces double as co-working spaces, but if yours isn’t one of them, research co-working spaces before you arrive, and reserve space there if necessary. Some cities are so popular with remote workers that co-working space isn’t hard to find, but they may book up fast, so if you need one, make sure it’s locked in before you head to that city.

I’m sort of obsessed with the Global Co-working Map now (I’d like to note that there are eight co-working spaces in Croatia calling my name). You’ll want to check to see if those spaces are available on a walk-in, weekly, or monthly basis, or if they require some longer-term commitment.

You can always fall back on time-honored digital nomad workspaces like coffee shops and the place where you’re staying, but one reason people do remote years is to form relationships with other remote workers. So, if you can, find a work home for each location you stay in.

Your transportation between locations is probably going to be your largest expense, so if you’re worried about cost, you can buy a round the world airline ticket, which allows you a certain number of stops within an overall amount of miles. For a good breakdown of different options with this kind of ticket, here’s a useful article.

If you’d rather not commit yourself to that kind of ticket, transportation between locations is one area you can handle as you go. You may find deals on flights, or alternate methods of transportation (for example, by water instead of by air), and being flexible here usually isn’t going to leave you stranded.

Have a backup plan. Think of a remote year as your business plan. You have contingency plans for work, yes? So do the same here. Think about what happens if your company undergoes restructuring while you’re working remotely — how could you stay in touch with what’s really going on?

What happens if there’s an emergency at home and you need to travel back quickly? What happens if there’s a natural disaster in the part of the world you’re in — how would you get in touch with your family or safely get out of the country?

Thinking ahead about how you’ll handle bumps in the road will give you more confidence about facing the unfamiliar. Less stress over potential problems with logistics equals more time to focus on the good parts of your remote year.

It may feel like you’re being too much of an Eeyore, thinking about everything that could possibly go wrong, but since you can guarantee that at least one thing, even if it’s small, will go wrong during your year, it’s better to have the right mindset of preparedness.

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How to Get Ready for a Remote Year

Even when you’ve got your travel plan worked out, doing a remote year isn’t as easy as packing a bag and heading for the airport. You’ll want to consider a few things before you start your adventure, like what to do with all your earthly possessions and how to stay in touch with both work contacts and your family.

If you don’t have a friend or a family member who can store your stuff, renting a storage unit is your best option. Be sure you choose a place that is environmentally controlled for storing things like electronic equipment or important papers.

Also, make sure you have a plan (and yes, a backup plan) to pay for that storage unit. You might pay for the whole year in advance, or set up recurring payments, but either way, make sure the company that rents the unit knows how to get in touch with an alternate contact if they can’t reach you while you’re in another country.

Some of the most popular remote year locations are in third-world countries, where the cost of living is extremely inexpensive for people coming from someplace like the U.S. This low cost for housing, food, and local travel makes it possible to start your own business or freelance while still being able to live comfortably. But it also means you’re moving into a culture that you probably won’t be familiar with.

If there’s one piece of advice you should remember from this article, it’s: don’t be the first-world asshole.

In other words, act like your momma taught you. Be respectful and polite. Be curious. Don’t be a know-it-all. Apologize if you screw up. Don’t expect to find food and drinks you’re familiar with, and don’t demand them when you don’t find them. Be careful when you go out by yourself.

Learn at least survival phrases in the local language, and try to use them, even if you feel like you sound like an idiot. For some quick pronunciation help, check out sites like Forvo. Get a translation app for your phone. Research local customs and laws. Register with your country’s local embassy or consulate.

I know I’ve said this a couple of times already, but consider the different locations you plan to stay in. Earthquakes, typhoons/hurricanes, local government unrest — not all the bad stuff happening in the world gets called out in travel warnings from the State Department.

Be aware and have a plan for how you would take care of yourself or evacuate the country if needed.

Along that same line of thought, make sure your family and close friends have ways to get in touch with you at your different locations. You might schedule regular check-ins (this means more than a Facebook post), and make sure someone has your itinerary. You can even keep your travel plans in Google docs and share the file so that as you update your plans, your family can see it in real time.

Working During a Remote Year

Doing a remote year is all about the work.

Well, it’s about working how and where you want to work, but the actual work you do is still the focus.

You want to juice your creativity by engaging with different people in different places. Put a spark to all those creative ideas running around in your head. Who knows what kind of partnerships or business ideas you’ll come up with?

Putting yourself in a situation where anything is possible lets you stretch your personal and professional self.

Remote years are a great time to figure out if you want to work for yourself, either by starting that business you’ve always dreamed about, or by freelancing for multiple clients. Or both.

If you’re not sure what kind of work might be available, read up on becoming a digital nomad or look through sites like Upwork to see what kinds of jobs are out there.

When you arrive at each location during your remote year, you have a chance to expand your professional network. Don’t be shy about asking other remote year participants and digital nomads about opportunities they might be aware of. And on the flip side, be willing to share the opportunities you know about.

What if I Already Have a Job?

You may have a job you love already, and are just looking to work differently. Now you have to convince your bosses that spending a year out of the office is good for them, for your clients, and for you.

What can you do for your company from different locations around the world? If your company has a global presence, maybe you can be their point person in another time zone (offer to save them from really early or late conference calls). If your company has locations in other countries, can you work part of the time from there?

What will your year bring to the company? Don’t just argue for the idea of creativity and flexibility. Will your year put you in contact with potential new clients? Outline who those might be and how you plan to engage them.

Is there a project that needs focus, but that no one in the company has taken on? Offer to be the point person, and make that the centerpiece of the work you’ll do over the next year.

Is there a client that needs some extra attention? Again, you can offer to be the point person for that client. Be specific and detailed when you outline how you can help your company and their clients by working from different locations over the next year.

When you argue that it’s good for you to do a remote year, keep in mind that you’re talking about good for you in terms of the company you work for.

Create a plan that makes you a pathfinder so that if the remote year works, others can do the same thing. Show how a remote year helps prevent burnout. Give examples of other companies successfully using remote teams.

Be clear with how you plan to stay in touch with your bosses and your team. Give them a plan for updates, check-ins, and status reports. Tell them when you plan to work, and how you will be in contact daily.

Regardless of whether you’re working for a company or for yourself during your remote year, stay organized and focused on the job, and no matter where you go, you’ll find opportunity.

When Do I Go Home?

Unless you’re doing a specific program that handles arrangements for you, your “year” doesn’t have to be a calendar year. It could be 10 months or 14 months. That’s the beauty of working remotely; it’s all up to you.

So, when do you go home? Or perhaps a better question: do you go back home?

It’s such a personal decision, and depends on so many things. Are you comfortable moving from place to place, or was your remote year an adventure that you’re glad you did, but not ready to do again?

Are there places you didn’t get to go, and can you work those locations into your next round of travel?

Are you getting work done? Is your employer okay with you continuing to work remotely?

It’s a little old school, but the pros/cons list is a good way to think about all the reasons why you might or might not want to keep going.

You might decide that you want to continue to work remotely, but that you move every four or six months, instead of each month. This is more of a location-independent work style (living and working from a home base, while traveling and working from other locations frequently).

No one can make the decision for you. It’s a balance of personal comfort level, productivity, and the needs of your work team.

Making It Work

A remote year has a lot going for it. The flexibility, innovation, and persistence required to jump from location to location around the globe for a year can also jump-start your creativity, make you part of new communities, and give you a new outlook on your life and career.

Just remember: have a plan and a backup plan. Think through how you will handle the year, from both a lifestyle and a work-style perspective. Be detailed and be realistic.

Then go for it!

Photo credit: londondeposit

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