Traveling on the Street

November 21st, 2019

Over the past year, I’ve had the extraordinary opportunity to spend over half of it living and working as a software developer in seven different countries around the world. Solution Street has been willing to support my desire to see the world by allowing me to work remotely from anywhere in the world. While traveling, I’ve learned many things, about myself, about the countries I’ve visited, and about how to better lean into both work and life in my work-life balance. When gallivanting from Mexico to Korea to Europe, exciting experiences and unexpected challenges certainly came up, so I’d like to share some of the lessons I’ve learned so others may benefit.

The Primacy of Work 

When working remotely abroad, one of the most common misconceptions is that you will have the freedom to explore and experience the city in the same way as when you are on vacation. Despite knowing that you are still working a full eight-hour day, it’s assumed that you will have the time to see the sites, eat the specialty foods, and generally pack in all the same level of tourism as when you are in a country for vacation. Even other remote workers, especially ones just beginning to travel, fall into this trap, and find themselves taking extraordinary amounts of time off to live the vacationing lifestyle they’d imagined.  

More than a few of the people I’ve met while traveling have found themselves jobless soon after leaving their home countries due to a desire to live life on the road as if they’re on vacation. Sightseeing during the day or partying at night, can result in missed meetings, a precipitous drop in productivity, and even a lost job. Although a few people I’ve met are able to rally and find a new job while outside their home country, more often than not this vacation-minded lifestyle will cut your travel short from lack of funds, the need for an in-person interview to get a new job, or a realization that you need to reorient your priorities before continuing to travel. 

Your remote job is what allows your remote travel. It’s easy to forget how fast funds drain, even in a cheaper country, when you live life like you’re on vacation. This is why, before deciding to work remotely, it is imperative that you make an honest and detailed assessment of yourself and the work you do to see if remote work is a realistic possibility for you.

Can My Job Accommodate Fully Remote Work?

Your company makes the final decision on if, and to what extent, you can work remotely. While you may think there are no issues, your company may not agree. There are a few things to consider including taxes, scheduling, and communication that will help you know if your company has the means to accommodate your remote work. The first and most important thing is to look at how communication and meetings are handled at your job. Even fully remote companies often like to have face-to-face reviews or all-team meetings from time to time, and knowing if these can be attended remotely, or if you can schedule yourself to be back for them is essential.

Plan ahead so that you can make the most of your time in a new location. Communicate, early and often, with your company on any scheduling issues.

Extraordinary work situations also need to be considered, especially at a company with multiple clients. While one project may be remote, another may be onsite. Even the transition from one remote project to another may require time back in the office. How these and similar situations will be handled, and how and whether you can accommodate them yourself, need to be considered and discussed before you leave to work remotely in another country.

Finally, it goes without saying that there is a huge difference between working down the road from your office, and working from another country. Asia, Europe, and even somewhere as relatively close as Latin America each has its own hurdles, and each has its own nuances. Having frank and open conversations about where you plan to go, how you plan to adjust your working schedule, and what concerns your company’s decision-makers have help keep your company comfortable and worry-free. Trying to keep it a secret is flirting with disaster.

For instance, I had a friend who had been traveling and working remotely in Latin America for three months without telling his company where he was. He had a fully remote job, and worked the same hours, so his company had no idea he was traveling. However, one week his project ended and he was asked to come into the office for a meeting to discuss what his next project would be. When he broke the news to his company that he was in Colombia, nearly four thousand miles away, it was an unpleasant shock to them. A large multinational corporation, his company had offices there, and were very worried that they were breaking laws by “allowing” him to work from there. A few days of panic and angry meetings resulted in his having to buy an emergency plane ticket home. My friend now finds himself on a much tighter leash — and without a remote project.

Because my friend never had  a full and frank conversation with his company before he left to work outside the United States, his travels were cut short, he lost his company’s trust and his ability to work remotely, and he is likely lucky to still have his job. With an appropriate conversation, he could have prevented this panicked response and been able to plan his trip appropriately and work from countries where his company wouldn’t have worried. Your company always has final say in whether you can travel and work, for they may have concerns that we, as employees, are not necessarily thinking about.

Can I, Personally, Work While Traveling? 

Working and traveling cannot be managed by everyone. While hugely rewarding, it can be, and often is, a tough, lonely, and exhausting way to live. Traveling and working is not the idyllic life I believe many imagine it to be. It is not the long vacation many expect, although it does allow for many great new sights, cultures, foods, and all kinds of other experiences that entail a lot of distractions. Before packing up and moving, it’s necessary to take an honest inward assessment on whether or not you, personally, can handle traveling while working remotely abroad.

Before I tried to work while traveling abroad, there were a few things I knew I needed to prove to myself, about myself, before I suggested it to my company. The first, and most obvious, was my ability to work remotely. When I started working with Solution Street, I had not previously had the option of working remotely, and although I knew I wanted to be able to travel abroad, I also knew there were many people who, as soon as they left the confines of an office setting, lost the ability to work with any semblance of efficiency. To test my resolve, I worked remotely from home for long periods. As remote work became more common and my hours working from home increased, I was very cognizant of how efficiently I worked while at home. I even tested working with distractions, working during at least some part of a few family vacations. While I do not necessarily recommend working while your family is on vacation, it served as a great personal test by proving to myself that yes, I could work with significant distractions waiting just outside the door.

The temptations offered by distractions only continue when you work remotely, especially if you have friends with work schedules different from yours. While traveling I met people who used all of their vacation within the first two months of working abroad, people who missed meetings due to partying on the night of a local holiday and then oversleeping, and those who just forgot about work entirely and lost their jobs. If you cannot handle the temptations offered by distractions to buckle down, do the work that needs to be done, and be available when required, you might need to work on fixing your habits before looking at traveling.

Logistics and the Importance of Good Planning

Before even arriving in a new place, the first thing is figuring out a few things for day-to-day life. Do you want to live in a more foreigner-friendly, touristy area, or do you want to brave a less active, less touristy place? Where will you work? Will you rely on your Airbnb, a workspace, or cafés to get connected? What hours are you going to work; will you keep the local work hours or your home work hours? Do you have a set amount of time you are going to stay, or do you want to leave that open ended? What will you do if something essential breaks?

Figuring all this out takes time, and for me is the most stressful part of working remotely abroad. While it becomes easier as you get a better sense of what you like, get more friends who can advise you or revisit places yourself, for me, it is still stressful. It is, however, essential to have done this part well, so as to ensure you can both live and work as comfortably as possible. Doing it incorrectly can ruin your experience in a country.

Where to Live, Where to Work

Deciding where to live and work is a very personal thing. Some people love being in the center of the city, others love being in quiet areas and traveling in for experiences. I know people who always work from home, and others who go around the city going to two to three cafés each day in various locations. Knowing what you prefer is essential in choosing what to do. For instance, I love being in the center of the city or near friends, largely because after a full day of work, dragging myself out on a trek is a huge struggle. What you decide is best is largely a personal decision based on your personality.

What I think is essential, no matter what you plan, is to always have a backup. While working abroad during my most recent trip, I had a complete loss of my Airbnb’s Internet reliability. As someone who was using this “second” home as their primary workspace, this more or less meant I was stuck without a way to work. Luckily, I had a friend who worked at a co-working space nearby, and I was able to quickly sign up and set up in a new location. Having a backup for Internet when traveling, whether it be a café or two (or three) with reliable Internet, a co-working space, or something else, will be an essential part of my travel preparation in the future.

How Long to Stay in a Place

Until you are very familiar with the new area where you are staying (or have friends who are), planning well, picking a place, and staying there for an extended period is invaluable. It allows you to figure out the city and the culture of where you are on a deeper level, while also allowing you to calm down and spend the time to work well, make friends, and not be distracted by the fact that you may always be moving (as I was). Even among cultures and countries you think you know pretty well, you will benefit from a longer stay if you are visiting a new city.

Most companies that offer organized remote work programs do so for one month per city, and many people who do these programs (often newer travelers) initially think of this as a long time. It’s not necessarily, though. Most of the people I’ve talked with in these programs find at least a few cities where they realize they’ve only scratched the surface of what they’ve wanted to do. In my experience, deciding to leave a city that you’ve tired of after just a week often occurs because you haven’t given it a fair try.

On my trip to Korea, the whole of Seoul came across as very sterile and similar to other large cities around the world. One neighborhood had the same chains and the same big streets, with only a few markets here and there. That was my experience — until I started getting bored with crossing the same paths, and started going deeper into the alleyways. There I found many traditional Korean restaurants and wonderful places without the gilded polish of the main streets. It took a little over three weeks, but a whole new world was exposed just minutes from where I lived and worked, simply by my going off the beaten path. And I never would have discovered any of this if I had given up earlier.

At this point, I prefer to have at least six weeks in any new city, as this is the amount of time I’ve found really allows me to get comfortable with a place, and get out to not only do the tourist stuff, but also to do the more interesting things you don’t find until you really live in a city. I certainly have friends, more experienced travelers, who stay in places for shorter durations when returning to places they’ve already experienced, but even they have told me that a long stay is helpful in new places.

The Hurdles of Time

The final logistical hurdle when it comes to travel is figuring out what hours you will work. When you stay in the same place, the traditional nine to five, with maybe an hour two of variation here or there, is a pretty standard system. But when traveling the world, time zones become a huge hurdle. While companies can be nice and allow you some flexibility, the onus is on you to adjust your life and your sleep schedule around the hours you need to work — even if that means taking the graveyard shift.

Most companies have core hours to allow for calls and meetings, and the amount of flexibility a company can or will allow an employee on not working during those hours is totally in the company’s discretion. No matter the country in which your office is located, there is someplace on the globe where your standard business hours are in the middle of the night. For the United States, that’s Asia, and if you want to work from there, you have to consider whether or not working until 6 am is something you want to do. The hours of the day (local time) that you have to work should be a central point in deciding where on the globe to go.

As a computer programmer, I’ve found that the flexibility I and my peers have is much higher than, say, for someone in sales or HR. Being able to work relatively alone without the need for long meetings and calls allowed me, for instance, to work in Asia with only a few hours spent working the night shift to overlap with the east coast of the United States. While you may still have the occasional meeting at four in the morning, this flexibility is something that really allows for better travel.

Regardless of how flexible your schedule is, though, looking at the time difference and discussing the possibility of flexible hours, and finally deciding to what extent you are willing to adjust your own life to travel is essential when looking at the more difficult time zones. Having just returned from a thirteen-hour time difference, I will definitely say there are pros and cons to working weird hours. In Asia, I split my workday, working four hours during my local nine to five time frame, and the other four hours from 10 pm to 2 am to accommodate the nine to five time frame on the U.S. east coast. A schedule like this allows for some daylight hours for exploring and seeing the sights, and also means that any late night weekend events are a lot less taxing, as you’re already used to the schedule. However, there are certainly cons to setting your schedule up this way. As the night hours wear on in a silent city while you work away, sleep can be hard to fight off until you adjust to your new sleep schedule, and I found it essential to keep an hour or two after work for winding down to assure I never fell asleep at the keyboard.

The Challenges and Rewards of Working Remotely 

I’ve been emphasizing and re-emphasizing that working remotely is not like a vacation. In fact, it’s a lot more like living in places for a short time while constantly moving, with all the routine-breaking, friendship-straining, life-rearranging that entails. Meeting people in a new place, going out to see a city after working hard, and figuring out the logistics of travel can all be draining things, but it’s also essential to fully appreciating what you can do as a digital nomad.

Getting Out

Working abroad quickly allows someone to fall into the same ruts that they do at home. After a long day of work, going home to binge Netflix, and only going out on weekends to one brunch place you know can become a routine almost overnight. Although this lifestyle is possible while working remotely abroad, not falling into this trap is essential for a meaningful travel experience. This not only means taking some time when living in Peru to go to Machu Picchu, it also means making sure to get out in the city in which you are staying and discover its unique places, food, and  culture.

As a bit of a homebody myself, this is one of the things I struggle with most. I’m quite happy not leaving the house for a day or two, and getting into the habit of forcing myself out of a comfortable place to see a new place or experience a new restaurant is probably the greatest skill I am learning while traveling. Going out after (or before) a long day of work when tired, doing the touristy things you would put off to the last week (and then miss), and eating that weird food that is a delicacy but sounds disgusting to you are all important parts of travel — and you’d be surprised how easy it is to miss those.

Being able to get out and explore the place you are in is essential when in a new city and country, but is as valuable, if not more so, when in your home city. As a DC native, who still uses the city as a home base, it’s remarkable how many great places I get introduced to by relatively new people in the area. Without their new perspectives and fresh input I would likely not often venture beyond my old stomping grounds.


Depending on who you are, the number of friends you want and the amount of human interaction you need can vary dramatically. However, none of us can be alone for too long without having loneliness take its toll. Especially in a new country with a foreign culture and a language you don’t speak, the need for a friend can become acute quickly. How each person deals with this varies, and I am still figuring out my own best strategies. Below I’ve listed a few ways I’ve dealt with this, and how others I’ve met have handled it as well.

The first, and easiest way to address this problem, is to travel with a group. Companies like Hacker Paradise and Remote Year set up group programs for remote workers in cities around the world. There are pros and cons to both programs, but both provide a community, an apartment, and a workspace for about $2,000 per month. The price is steep, especially in those countries where you can find housing for a quarter of that price, but the communities are super helpful. I’ve kept in contact with, and seen while abroad, friends I met on these programs long after the program was over, and they are resources I use whenever I am thinking of a new place to travel. For people just starting out with traveling, I recommend using one of these kinds of programs for the community aspect alone.

Outside of paying for a program, meetups and other activities are great ways to meet other travelers, as well as locals and expats in the community. Active hobbies also make for great social experiences, and I’ve met people who travel and meet people via dance classes, running groups, martial arts classes, or even basic fitness classes at a gym. As an English speaker, it’s also relatively easy to find people who speak English, and want to speak it better. While the most gregarious of my friends will just talk to strangers wherever they go, language exchange meetups and bars exist around the world and are designed specifically so strangers can talk and practice a new language and can be great places to make friends. Computer programmers will also find hackathons and meetups around the world. While many of these will be primarily in the native language, coding languages are the same everywhere and it’s a great place to meet people who have the same interests.

Probably the most common method I’ve seen people use to find a social circle is traveling to where you know people. As you travel, you meet more people who are either expats, or who live the same lifestyle. Once you have a group of friends who travel, or once you have access to communities like Remote Year and Hacker Paradise, it becomes safe and easy to drop into a place where you know at least one person. While this can severely limit where you go, as you are limited by people you know, it’s probably the easiest and most comfortable way to begin working in a new city.

The people you meet abroad may not always be similar to people you would have met at home, and some of my favorite people are those I’ve met while traveling and working remotely, including some who I don’t think would have ever been in the same circles as me at home. And once you find a group, you’ll find the places you would have overlooked, skipped or been too lazy to go to are a lot easier to get out to, and the trip itself becomes more rewarding.


Working remotely and living the life of a digital nomad has been a fantastic opportunity, and one I hope to enjoy for a good deal of time to come. It’s allowed me to experience new places, meet incredible people, and learn a lot about myself as well.

To summarize what to know before you travel:

1. Be honest with yourself and talk with your company about whether working abroad would work. Can they support it? Can you handle the distractions?


3. Know the challenges and low points you might face and be prepared for them.

While living this life is not without its challenges, I believe that the rewards far outweigh the risks. Enjoy the journey!