While I cringe at the thought of referring to myself as a “digital nomad” or even a “travel expert,” with over 3 years of remote work and 42 countries visited under my belt, I figured I might have some valuable information to share with others who may be intrigued in dabbling in this sort of lifestyle. I’m lucky, GetMyBoat is a very cool company in that most employees work remotely, enjoying the lifestyles they want while getting their work done.
This advice is not intended to sell you a BS course on how to open an online store or some other scammy way of making money. If you want just to sit back and drink Bintang in Bali as the money rolls in, I can’t help you. Surfing and eating smoothie bowls all day isn’t going to lead to a stable income or a sustainable lifestyle on the road. I still have no idea what dropshipping is, but I can almost guarantee it’s not the way you’re going to make money while traveling abroad. But if you’re willing to make a lot of sacrifices, work hard, be online at weird hours, and take on the challenge headfirst, then maybe I can help you.
My glamorous getup for working from home
Types of Jobs
Startups
Startups have been where I’ve found the majority of my online jobs. Startups are scrappy – they don’t subscribe to confined office spaces and often don’t have the budget to afford a massive team of top talent to live and work in expensive cities like New York and San Francisco. They are willing to compromise and hire remote workers, even across a wide range of time zones. Startups are fun and exciting to work for – you get to be a part of building a project that could become the next Uber or Airbnb. Often, your ideas and input are valued and used in a way that is impossible at large corporations. Working remotely for a startup is one of the best ways to have consistent employment, earn a decent salary, and learn a LOT about what it takes to start and run a business.
The downsides of working for startups is that they can be less stable than working for large corporations. They open and close all the time, running out of VC funding or are bought out by bigger companies, leaving employees searching for new opportunities with little to no notice.
Small Businesses
Similar to start-ups, a lot of small businesses are more open-minded and flexible when it comes to working conditions and work-life balance. They may not have the office space to house you and will be open to you traveling abroad while getting your work done – provided you’re available online at set times. Internal recommendations, getting to know upper management, or offering your services to a small business owner can lead to a lot of lucrative and stable working opportunities that you can do on the road.
Freelance writing
Freelance writing is one of the best ways to crack into remote work. There’s a demand for writers for all types of content – from technical to grant writing, creative pieces to medical. The kind of freelance writing you’ll be able to do depends entirely on your qualifications and educational background. Create a portfolio of articles to send off to publications or other organizations to showcase your skills and spark their interest.
For technical freelance writing, you can earn various certifications to open doors to higher paid positions. These courses are often offered online and can be completed in addition to holding other jobs.
Video editing
If you have a talent for creating and editing video content, there is a lot of work out there for you. You’ll need to have all the relevant software like Final Cut or Creative Cloud, which can be a significant initial investment, but if you already have it from past projects, there’s no reason why you can’t find clients online.
Programming and software development
As a non-technical person myself, I can’t provide a ton of insight into finding these types of jobs, but I do know that they require a LOT of skill and you shouldn’t expect to become an expert in Python or C++ overnight. It’s a great option for remote work for software developers or computer scientists who spend their whole day in the office behind a computer not talking to anyone. There’s no reason why you can’t do that while in a different country, and many companies are open-minded about having their tech team working from abroad.
Marketing + PR + Social media management
This is my area of “expertise,” so I can say with confidence it’s possible to do these types of jobs remotely – but again, it depends on the company. I’m fortunate, my company is small and very pro-working online. I don’t have a big team to coordinate my marketing campaigns and projects with. As everything is becoming digital and moving online, work for these departments is also transitioning away from the analog methods of the past.
Customer service
There are lots of customer service roles available online, some for monitoring online chats, emails, while others require you to be able to take phone calls, but your location doesn’t matter. Tools like Google Voice, Skype calling credit, and other methods of international calling are breaking down the barriers for customer service agents to move abroad and live out their travel dreams when they aren’t resolving complaints.
English teacher
While these positions often come with some regulations, like requiring an American/Canadian accent, a TEFL certification, or other qualifications like a teaching degree, they can be excellent sources of stable income. Companies like VIPKids, DaDaABC, English Ninjas, to name a few, offer a competitive hourly rate to teach students of varying levels. Be aware that you might need to demonstrate a certain level of enthusiasm and English-teaching skills to land the position. I failed the VIP kids interview epically. I can’t get that excited about teaching simple English words, and I guess I don’t like kids virtually just as much as I don’t like them in real life. Another form of teaching online is tutoring other subjects – check out platforms like Varsity Tutors if you’re qualified to tutor and teach in other areas like standardized test prep or any other school subject, including other languages.
Be aware that these companies can also require that you work at hours that might not be ideal, depending on where you’re based.
Me as an English Teacher in Spain on my last day!
Translator
This job requires fluency or proficiency in another language, obviously. You may have to provide some proof of competence, whether that be samples of translated work or results from a standardized exam. These jobs can be competitive and difficult to crack into initially, but you can read and write in a less-common 2nd language, like Russian, German, or Chinese, for starters, you can find a TON of high-paying jobs online for translating.
Asking your current employer
While it may feel like a long shot, you never know when your boss is going to say yes to a request. If you work primarily on your own and only communicate with your other team members via email or other electronic means, you might be able to convince your boss you could work remotely. Make sure you sell them on the benefits to them – they can use your desk space for someone else, you could negotiate working remote instead of your annual raise, or find another way to start working in an office in an exotic place. My main argument to managers and bosses who don’t think they can trust their employees to work from home is this – if you can’t believe that someone is working at home, how can you trust they are working while in the office? Either you get results or not, and working from home will put extra pressure on to perform and succeed!
How to find a job
Step 1: Update your online presence.
If you want to work online, you have to exist in the online space. It’s tricky enough convincing people that you’re worthy of being hired in a real-life interview. Online is even more complicated.
You need social profiles and other content that showcases who you are as a person so that hiring managers can feel confident that they aren’t hiring an imposter who isn’t going to add any value to the company. Clean up any old tweets or unflattering photos. Update your LinkedIn profile and make sure it matches all the content on your resume. Putting yourself out there in a positive light will help to instill confidence in recruiters and people looking for remote workers, and by being active and available online, you’ll demonstrate a level of reliability and “realness” which is crucial when you aren’t interacting in real life.
Step 2: Create a portfolio
The type of portfolio you create will depend on your industry and the kinds of jobs you’re looking for. Making a personal website is a good idea for people of almost all sectors, especially when you are responsible for creating something – whether it be written projects, visual works like videos or photos, coding or applications, or it could just be your corner of the internet to brag about yourself to anyone who stumbles upon it. Seriously, it’s your place to shine. You want anyone who finds it to think – I want this person to work for me!
While I’m not a full-time travel writer or blogger, my travel blog helps me to find writing jobs and freelance projects. It started as a hobby after a trip to New York City back in 2011 when I visited a friend for the Macy’s Thanksgiving Day parade. Over time, it became lucrative and is my place where not only do I publish my thoughts and details about my travels, but also my accomplishments as a marketing & PR specialist. It’s a great way to back-up my resume and job applications, and it’s a fun thing for me to create.
Use GitHub if you’re a programmer. Use WordPress if you’re a writer. Use whatever platform helps you to highlight your achievements and strengths in the best light.
Step 3: Apply & reach out.
In addition to submitting applications, you’re going to want to get in touch directly with hiring managers and recruiters who work in filling fully-remote vacancies. Remote work is becoming more popular as employers are evolving and opening their minds, so connecting with someone who has access to these positions and is looking to fill them is going to be a massive help. Don’t be afraid to send messages on LinkedIn or even get ahold of relevant contact’s work emails to shoot them a note and express your interest.
A few remote-only job sites to look at include FlexJobs, WeWorkRemotely, Remote.co and Jobspresso. AngelList is excellent for connecting with startups. There are many more job site search engines, and they vary in accessibility – some require a paid membership to access the job postings. These are more competitive, but if you have a lot of industry experience and an impressive resume, you could have a lot of luck right off the bat when job searching. You can also use regular job-search engines and throw in keywords like “work from home” and “remote” or select the “telecommute only” box on the filter selection.
Try Craigslist. Sounds weird but you can find lots of remote jobs posted on websites like this. You have to be careful and wary of scams, never give out personal information without some verification that the job posting is legit, and NEVER pay to apply for jobs.
Upwork. I’ve finally had a bit of luck with freelance writing projects coming through on Upwork, but I’ll admit, I was skeptical at first. The problem with resources like Upwork and Fiverr is that they often are full of workers in foreign countries who are willing to work for preposterously low wages, undercutting you as a freelancer and making most projects not worth applying for. I have a friend who makes a lot of money off Upwork projects, but even she admitted that it took a while to establish herself on the platform to start receiving the higher-paid projects.
Living Abroad
Where to go?
Deciding where to go can be tricky! There are so many amazing destinations around the world, some more “remote worker” or “digital nomad” friendly than others, and you have a lot of things to consider when choosing. Is there reliable, strong internet connections? Is it safe? What about the time zone – do you have to sync with the 9-5 hours from back home or is it okay if you work a more flexible schedule?
Determining the answers to these types of questions is going to make a huge difference in your experience as a remote worker and traveler. So far, I’ve had some of the best WiFi and remote-working facilities in Singapore and Bali, while Australian WiFi is absolutely horrid. Having a flexible schedule made it easier to work while in a different time zone than my boss, but traveling in South America has made coordinating easier. There are pros and cons to lots of different locations, so make sure you do some thorough research at the beginning. You want your transition into this lifestyle to be as seamless as possible.
Legal considerations
Living abroad, while fantastic in so many ways, can be an absolute nightmare in others. One, in particular, is with all the legal crap that no one wants to think about, like taxes and visas.
It’s crucial that you carefully track your income, especially when you’re a freelancer and have money coming in from a lot of different sources. Use a bookkeeping software or at the very least a detailed spreadsheet, save your receipts and invoices, and get in the habit of keeping all this information in an easy-to-access spot. You will thank me come tax time. It’s also worthwhile to investigate what exemptions you’re entitled to when living abroad – some foreign-earned income is tax-exempt, and you can often get out of paying certain taxes by living abroad.
Visas are another important if not essential thing to always be researching. Certain passport holders will find that they have a lot of privilege and flexibility when it comes to their travels – as they are less restricted in where they can go and for how long. But no passport lets someone travel EVERYWHERE without any restriction, so even if you hold the coveted Singapore/UAE documents, you still need to research where you’ll need to apply for visas before arriving in the country. Even if traveling to a place is visa-free, there is typically a limit to how many days you can stay.
Always investigate what sort of visa you will need, how long it allows you to stay, and when possible, apply for it early, so you aren’t scrambling to get it approved before your flight.
Vaccinations
This isn’t relevant to all travel destinations, but you’ll want to do your research before booking your flights to figure out what shots you should get before venturing abroad. I just recently got my Hepatitis A, Typhoid, and yellow fever vaccines. It was not a cheap visit to the doctor, but I’d rather pay now and avoid illness later when traveling. Always read up on local recommendations, and it doesn’t hurt to travel with a stash of medications in case you get sick and don’t have immediate access to medical assistance.
Speaking of medical assistance, another significant travel and living abroad consideration you cannot neglect is insurance. Not having health or travel insurance can be catastrophic if you get injured or sick during your time abroad. There are so many different options for medical insurance – your current provider can offer you a plan, or you can invest in various travel insurance companies to cover you during your adventures abroad.
Finding accommodation
If you’re traveling on your own, my top two recommendations for accommodation is either to book a room in an Airbnb that you’ll share with others or a private room in a hostel. Unless you’re planning to spend lots of time in co-working spaces, you’ll end up being alone a lot if you rent apartments to yourself. It can become lonely if you don’t make an effort to meet new people and integrate yourself a bit when traveling to a new location. This could be different if you’re in a place like Chiang Mai, Thailand, a hotspot that is crawling (probably quite literally) with other “digital nomads” and expats that you’ll meet while exploring the city.
What to bring
Less is more. While I am the biggest violator of this rule, aiming to have 25% of your suitcase or rucksack empty when you set off on your adventures is a great way to do it. You’ll always accumulate new stuff, and for whatever reason, your bag gets heavier and fuller each time you repack it, regardless if you’ve bought new stuff or not. If you haven’t worn it at home in the last month, you won’t wear it on the road. When in doubt – leave it out! You can always buy new stuff if you end up REALLY needing things.
To sell or to store – what to do with the stuff you leave behind
You’ve made the decision to go, and you’ve packed up the essentials. Now, you have the issue of dealing with all the stuff that isn’t coming with you. What to do? Sell it all off? Donate? Or, pay for a storage unit?
I’m lucky in that my parents still live in a sizeable home that has space for all my stuff (aka my childhood bedroom), so that hasn’t been stress in my life. My recommendation would be to ask yourself how long you foresee yourself enjoying this lifestyle. Just a year or less? Don’t get rid of everything, see if you can store it somewhere, so you don’t have to re-purchase big items. Downsize your wardrobe and donate clothes you won’t miss. It’s a good time to binge watch documentaries on minimalism and question what stuff is important to own for you.
Balancing work + travel
I have a few strategies for avoiding the dreaded “travel burnout” that seems to affect so many influencers and full-time travelers. It’s true that after months on the road, sleeping in different beds, all you want is your own bed and a normal routine. It can also hurt your productivity and ability to work effectively, which is something you have to avoid as a full-time remote worker.
The first piece of advice I can give you is to carefully plan your travel days. Saturdays are great for making transitions since flights are generally cheaper, and if you’re working on a 9-5 Monday-Friday schedule, no one in the office will know that you’re on the move. It’s also wise to select a time to move when things are fairly “quiet” at work – when you’re managing big projects or trying to meet hard deadlines, the last thing you want to do is pick up and jet off to a new city. Be strategic and get your accommodation set up beforehand so the transition is smooth and doesn’t have any negative impact on your work schedule.
Another thing I’ve begun to indulge in during this past year of traveling and working remotely is spending more money on getting from the airport to my new accommodation. While it may sound trivial, there’s nothing I hate more than the period between when the plane lands and when I arrive at the new place I’ll be “living.” I’m sick of hauling my 50-pound backpack on buses, transferring to trains or through metro stations. Unless it’s prohibitively expensive, I’ll get an Uber or a taxi from the airport to my accommodation to take some of the pain out of this process. Everyone is different – this might not bother you so much, but I’ve found it makes me much less crabby, so it’s worth it.
This rolls into the self-care routines that I work to practice, even while on the road. No, I don’t just mean getting massages, drinking wine in a bathtub, or buying myself nice gifts. Self-care while living a “nomadic” lifestyle means taking time to meditate, exercise, and do what I need to feel “normalcy” even when the way I live is anything but. Calling my girlfriends back in the states for long chats, texting my family, taking time to think about my goals and long-term aspirations, managing my finances, and most importantly, taking care of my body with healthy food and exercise is crucial. If I couldn’t maintain a workout routine and healthy diet while on the road, I wouldn’t be able to do this.
Challenges
Family
While sometimes it feels like being away from family can be healthy for your relationships, the truth is, sometimes it’s very painful. Missing out on Christmas, other holidays, family gatherings, or just the comfort of stopping home for a visit can take its toll on the soul. My advice would be to block off time each week or every two weeks to call your close friends and family back home, keep up with what’s going on over text and email, and stay engaged however you can. I’d recommend always having enough money in emergency savings for a plane ticket home, in case something pops up last minute and you NEED to get yourself to your family. It will help put your mind at ease.
Relationships
It’s no secret that dating while moving around is a massive challenge. Unless you’re only looking for short-term relationships and flings, it can feel lonely. Finding a partner who can and wants to pursue this lifestyle with you can feel like an impossible task, and I wouldn’t recommend searching for it. If it happens, it will happen naturally, but if you are set on finding another “digital nomad” you could end up settling for someone who isn’t right for you, but just also happens to work remotely. Get used to being alone, take yourself on dates, or search for travel friendships instead of intimate romantic relationships. If you do have short flings, enjoy them for what they are and don’t get too wrapped up in the idea of a future. If it does work out – great! If not – don’t let it get you down.
FOMO
The fear of missing out, even when you’re in a tropical place working on your laptop, is still a reality you’ll have to deal when traveling the world and working remotely. To cope with this, I practice a lot of mindfulness, meditation, and work on recognizing gratitude for the lifestyle I have and the experiences I get to have that my friends back home do not. It also motivates me to seize my time when I’m back home for a visit – making sure I spend adequate time with everyone I love, doing fun things and making memories when I can.
See your people when you’re home!
Financial management
Many travelers, digital nomads, and freelancers can find it challenging to manage their money, and many get themselves into a lot of trouble while trying to make all their travel dreams a reality. It can be easy to get caught up in the excitement of being in a new place and thinking “screw it, I’m doing this excursion, experience, whatever” instead of taking this “lifestyle” seriously and managing your finances as you would if you lived back at home.
While I personally don’t use one, this is where creating a strict budget could come in handy. Allocating some money for travel and fun, while making sure you’re achieving your savings goals and ALWAYS having an emergency fund will help prevent any financial problems from popping up when on the road.
Sense of community
After several years of moving around a lot, this is the struggle of remote work and travel that is hitting me the hardest. It’s hard to develop yourself or your hobbies when you’re always on the go. I’d love to learn to surf, to join a choir, to practice yoga more regularly, and belong to a gym, but it feels impossible to do these things if I’m changing locations every few weeks. After many destinations, it can feel like you’re always a visitor in a foreign place instead of being a part of the community fabric. One way I’d like to try to deal with this is by taking more initiative to find places to go without needing a membership, like buying individual yoga classes, taking a surf lesson or renting a board when possible, or working on this blog, which seems to be the only consistent hobby that I’m able to maintain.
Staying safe
Safety should always be a priority and consideration when making travel plans. Do your research on local areas, avoid getting to a new place at night, and do your initial exploring in the daylight before deciding if you’re in an okay area to be out in after dark. Check in with family frequently, so they know your whereabouts, and always read about the security offerings at apartments or hostels, whatever your accommodation may be.
I hope this post was a useful resource to anyone considering taking on this lifestyle! If you do embark on work + travel adventures, remember, it’s always okay to take breaks, to resume your old way of life, or stay in one spot for a while. You decide where you want to go and what you want to do – there’s no “one way” to do it!
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