What You Need to Know If You Want to Work Remotely and Travel the World

If you are fortunate enough to work from anywhere, you can take advantage of your freedom and work while traveling. Our very own Stephanie Lee has just spent the past nine months as one of these digital nomads with just a couple of suitcases and her laptop. Here are a few practical things to consider if you want to become one too.

Why would you want to do that

“Digital nomad” has become a disgusting buzzword, but it’s an accurate way to describe such a lifestyle. Freelancing is a more common way of making a living, and telecommuting has become an option for more full-time employees than ever before.

The digital nomad is essentially a remote worker, independent contractor, freelancer: anyone who can get work done from anywhere . If this describes your situation, you may be able to choose where you want to work day in and day out. (And if you’re not a telecommuter, you can even convince your boss to let you work from home if you’re up for the challenge!)

Sounds very exciting to be able to grab your laptop and work from Central Park, Tokyo, or wherever you go. Of course, in practice it is not always that easy. You may have obligations to your pets, your children, your extended family, your home, or your partner. If you do, you will have to consider them in your plans. However, even if you don’t have those obligations – say, you’re a lone renter with no pets or children – making a plan still requires a fair amount of preparation.

You definitely need a home base

The digital nomad is not entirely accurate. You still need a home base. Maybe this is your parents’ house; maybe this is your own home. Either way, your account providers, employers, and banks will likely need a physical address to create your accounts. Also, you need an address to receive mail.

The United States Postal Service offers several options to help you monitor your mail while you are away. For example, you can store mail for up to 30 days . If you return around this time, you will receive all delayed mail at once. If you are working for a long time, use their premium forwarding service to temporarily forward mail to your new address. Just keep in mind that if you are traveling you will need to update your forwarding address every time you move.

Of course, if someone lives in your home base, they might just hold the mail for you (and open up something important so you know what’s going on!)

“By the time I got back, my mail was mostly piling up,” Stephanie said. “I told my postmaster (my father) to mark all the important events for me. I’m lucky that someone did it for me. But this is really important: make sure to take care of everything online. “

For example, you need:

  • Sign up to receive account statements and payments online only
  • Sign up for direct deposit and ask customers to pay digitally
  • Make a list of quarterly expenses, such as registering your car or insurance (and you might consider changing your vehicle’s status to unused if you are leaving for a while). This way, you can set up a reminder to pay them online when they need to be, in case you are not at home to receive your mail.

The more things you can process on the network, the less mail you have to deal with and track.

You can also choose “Comprehensive Only” coverage from your insurance company. This provides basic protection against theft, vandalism, fire, or weather damage, which is ideal if you’re not going to drive. The operator may refer to this as “storage” mode. Stephanie switched her coverage to storage and it cost $ 50 a year.

Choose your temporary home and prepare for the trip

Stephanie went toJapan, Hong Kong, Taiwan and South Korea and had friends and family in several places, making life easier. If you know someone in a particular location and that person doesn’t mind a regular guest (or just a friend in the area), that might make it a more viable place to visit for a long time.

It’s one thing to be in a foreign place for a week or two, but there are some cultural considerations to consider if you’re going there for a while: language, for example.

It can be easy to get by with tourist-level fluency if you just have to ask where the bathroom is and where to get good food. However, when you are there for a short while, you may have to ask more difficult questions.

“Korea was probably the only country where I didn’t know any words,” Stephanie said. “Besides thanks and hello . In all other respects, I kind of knew it, or I could get by. For the most part, if you go to the big cities, you will be fine. “

Apps can help too. Stephanie recommends the free Speak & Translate app (for iOS and Android ), and Google Translate is another decent option .

There is also the question of health insurance. Your overseas health insurance differs, and you can check your Explanation of Benefits to see exactly what is covered and what is not. If you have Medicare or Medicaid, you do not have any coverage outside the United States . However, most private standard policies at least cover emergencies, and Budget Traveler explains :

If a member has chest pains and thinks they are having a heart attack, the emergency room visit will be covered, says Jackie Oh, vice president of product management at Cigna, “even if it turns out to be gas.” James Coates, MD, senior medical director for Aetna, says altitude sickness, fractures, dog bites, heatstroke and suturing cuts are also examples of what the standard will cover.

Conjunctivitis, poison ivy, mild cases of influenza, and other illnesses that do not pose a serious threat to life or health are rarely reported abroad. And even if the first symptoms qualify as urgent, you may have to pay for follow-up treatment abroad.

However, you want to check with your provider if you are truly protected. And if you don’t, or if you want coverage beyond emergencies, you have several options.

First, you can get travel health insurance, but keep in mind that it only lasts for a few weeks. It will likely set you back a few hundred dollars and is meant for short-term travel.

Second, you can also sign up for international health insurance in the United States, possibly through your current carrier. However, according to digital nomad Anna Wickham, be prepared to pay a couple thousand dollars a year.

On her website, The Worldly Blend, Wickham says the best option is to apply for international health insurance overseas – what she calls expat health insurance. She used a UK company called Integra Global , paying $ 500 for insurance coverage for six months. However, there is a drawback: you work in all countries except the United States. She explains:

If you include the United States, your health care costs for 6 months approximately $ 500 to $ 1,000. This is because the health care costs in the United States are absolutely incredible. Integra Global is not benefiting from my need for insurance in the United States. They simply cover the high costs of American health care.

If you are self-employed, you probably want to do the same deal, whether with Integra Global, Aetna International , Cigna Global, or any other international insurance company . When you return, you can reapply for coverage in the United States. If you are insured at work, chances are they won’t cover your travel insurance, but you can always check with your HR department. If you are only absent for a month, you can simply opt for travel health insurance.

Find a comfortable place to stay

While there are a variety of accommodation options , from extended stay hotels to hostels, Airbnb is the best option for many travelers. And it’s super convenient … but not for everyone . Discrimination on Airbnb is a big problem for many travelers, and it is not limited to minorities in the United States.

A tool called Innclusive (scheduled to launch in August) aims to fix that, and it is pretty much like Airbnb, except that it targets non-discriminatory hosts. Airbnb’s anti-discrimination policy, meanwhile, allows you to report any discriminatory behavior. When looking for hosts, you can also filter by Superhost, or at least hosts with a lot of reviews. This shows that they at least have experience with a large number of clients, presumably from different walks of life.

“I prefer large reviews because that way I know what to expect,” says Stephanie. “An experienced host will know not to cheat because they value a lot of reviews and super host status. They won’t risk you writing a four-star review instead of a five-star review. ”

When choosing temporary accommodation, whether it’s Airbnb or any other accommodation, there are a few specific things to think about:

  • Timing : Stephanie said she prefers to stay somewhere for at least a month. Thus, it gave her the opportunity to join the routine in this place so that she could combine her work with sightseeing. “I have been working for at least one month, so I don’t have to mess around that much. Otherwise, it really interferes with my work. “
  • Location: You also want to think about the location of your home. Is there a café nearby and Wi-Fi if you want to work outside your home? If you are going to rely on public transport, you will probably want to find a location close to public transport links.
  • Workspace : Since you still need to work, you will need a laptop-friendly space with a place that you can refer to as your office. Restaurants can grow quickly, so you’ll probably need a place with a kitchen as well.

Stephanie says she spent a lot of time pondering the reviews and talking to the hosts to make sure they knew her plan and could adjust. Often the rate is negotiable too, especially if you intend to stay for a month or longer.


Another tip: you can look for places where the owner lives on the site. That way, you have a guide to help you get settled, get around and give you recommendations, and you also have a friend because, as Stephanie points out, the life of digital nomads can be lonely.

How to set up a remote workflow

If you are working remotely, this probably means that you need Internet access. If you are visiting an area where Wi-Fi is not available, you may want to consider a mobile hotspot or router so that you have online access wherever you are.

Beyond the technical stuff, you want to establish routines and boundaries . You are in a new place, and it is tempting to just forget about everything and go explore. On the other hand, you can get so stuck at work that you never have time to leave your temporary home, which completely deprives you of the opportunity to be a digital nomad. Stephanie said:

You must adhere to your schedule very strictly. In the morning I worked until noon. Then I went out, had lunch, explored a little. Then I found a coffee shop and did the rest of the work. I gave myself one day – Saturday – when I say yes to everyone . During the week, I always thought, “I feel like I have to do this, but no, I really have to work.” On Saturdays I would just say, “Damn it, I’ll do it.

Presumably, you are in a different time zone than your colleagues at home, so this is another thing to fit into your schedule. In general, you want to create a schedule and then optimize it for your time zone. “Frontloading your work is key,” Stephanie said. She suggests identifying your busiest days and working those days like crazy, instead of trying to put it all in different directions. This gives you plenty of time to explore on less busy days.

You, too, want to be polite to your coworkers. Even as you upload your work ahead, you will inevitably have to communicate with them and you don’t want to text them or email them in the early morning hours, even if it might be prime time in your area. Technique can help with this. Most email clients allow you to schedule your messages so you can write them now and send them later ( Boomerang for Gmail does that too ). You can also snooze incoming emails to protect your quiet hours in your time zone.

Consider any additional hidden costs

Of course, the monthly rent of the premises will be your biggest expense. It may or may not be more expensive than renting an apartment in your hometown. Airbnb prices also vary, with significantly higher prices during peak tourist seasons or during major events.

“On the other hand, everything is furnished, and utilities are paid at the Airbnb price,” said Stephanie. I paid $ 1100 a month in Tokyo. This is a prime area and I can’t say for sure, but the market price is probably around that or higher. “

There are other, less obvious recurring expenses, for example:

  • Transportation : Stephanie says this can add up quickly, so you need to plan ahead where you are going and act effectively. Decide which parts of the city you are going to visit during the day and how you will get there, then plan public transport stops accordingly. You don’t want to travel to one part of town, only to buy another ticket back to your original location to complete an errand. Certain cities have passes, of course, and depending on the length of your stay, it might be worth investing in one.
  • Food : Even if you’re not really a tourist, you will probably still spend more money on, say, snacks than at home. Food and household items can be more expensive (Stephanie said peanut butter, fruits and vegetables were more expensive than she thought in Japan). The dollar may not take you that far, depending on where you go .
  • Coffee shops and Wi-Fi : Part of the fun of the digital nomad is to work from anywhere, and you’ll likely spend a lot of time in coffee shops while traveling. It can add up. If you join a coworking space, many of them charge subscription or access fees. However, you can save on this area by working for free at the library.

Of course, there are some savings that can offset these costs. You will save on gas if, for example, you decide to walk everywhere instead of by car. Bonus: you can explore more corners and nooks of the city as you walk.

You should also think about your taxes. Just because you can work from anywhere doesn’t mean you have to work from anywhere, so writing off any travel expenses can be challenging . The IRS states that in order to write off expenses, they must be “normal and necessary,” and this is how they define it:

Ordinary expenses are expenses that are common and acceptable in your trade, business or profession.

Necessary expenses are those that are useful and appropriate for your business. Costs do not have to be considered necessary.

If you’re a freelance blogger who writes regularly about travel, you may be able to write off some of your spending on digital nomads. On the other hand, if you are a freelance web designer, you will probably find it harder to justify the trip.

Either way, you are still eligible for a home office deduction just like any other telecommuting worker. Tax strategist and audit expert Tiffany Stokes told us:

Digital nomads are subject to the same tax consequences as those who work from home. Their place of residence and income is considered their tax home. They can take a deduction from the home office. If they are renting a room or hotel, they need to know how much of that space counts as their office in order to properly deduct the correct amount.

However, the rules are quickly getting complicated. Generally, if you are a US resident, you will have to pay taxes on your worldwide income. You are also not subject to income tax in most other countries unless you become a resident, but this may change if you stay in the country for too long. Here’s howStuart Patton, a tax attorney and expatriate entrepreneur, puts it :

Countries quite often treat someone as a resident for tax purposes only if they stay in the country for at least 6 months. It is often possible to restart the watch simply by jumping over the border for at least 24 hours.

So, just don’t stay in any country for more than six months a year, and you generally shouldn’t be subject to income tax outside the United States.

Patton is detailed in his full text, but it is probably best to work with a tax professional who understands these things. Use the IRS ‘Preparer Directory to find a legitimate professional, then schedule a pre-trip and after-tax appointment in April.

With the right preparation, you can work and travel at the same time if you have the ability to work from anywhere.

Stephanie admits that the digital lifestyle of nomads cannot be sustainable in the long term (mostly for sanity, she says). In the end, you have to go home, regroup and, you know, pick up your mail. However, it’s a great option if you want to see the world without disrupting your work.


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