Part 1: An Introduction to Working Remotely

So, You Want To Work & Travel the World?

Is your ultimate dream to work while traveling abroad? Even just ten years ago, options for turning a wanderlust-inspired lifestyle into a career path were generally limited to joining the Peace Corps, working for a multinational corporation, or teaching English in a foreign country.

These days, much of the world’s communication and commerce is conducted online—opening up new opportunities to earn a living working virtually. Even better, you likely already have some of the right skills needed to start, or transition to, a remote career!

But first, let’s get something straight: Unless this is the first time you’ve investigated the possibility of working remotely, you’ve likely already seen a number of bloggers, social media mavens, and ‘entrepreneurial gurus’ promise that—for a price—their ebook or online course will make the path to becoming a financially-stable remote worker a piece of cake.

This is not that guide.

Instead, we’ll show you how to find most, if not all, of the resources you need to develop marketable skills for free.

We’ll explore the many variables of joining the web-work-travel community—popularly called ‘digital nomads’—beyond picking an occupation or polishing your skills. This includes an in-depth look at all aspects of working remotely, including finding affordable short-term housing, ideas for what to do with your stuff while you’re gone, tips on navigating visas, what you need to prepare for long-term travel, and how to stay happy, healthy, and successful along the way.

We’re also not going to promise that it’ll be easy.

That’s because working remotely often requires that you blur the line between work and free time, especially when starting out. Trust me, it’s not all coconuts and hammocks! In the sixth article, we’ll explore the most frequent struggle remote workers face: burnout. That’s because many find it difficult to mentally leave the office, when ‘the office’ isn’t just at home—you carry it with you everywhere.

To help prevent burn out, financially or emotionally, it’s important to make an honest and comprehensive assessment of your personal qualities, skills, passions, financial health, and life goals. We’ll guide you through those all-important questions, starting with:

Is Working Remotely Different Than Working From Home?

If you already have experience working from home, you’ve certainly got a head start! That’s because remote-working opportunities share many similarities with working from home, the least of which is that neither requires you to be in a particular physical space. Both also demand that you:

  • Have the right mindset and personality traits. Namely, the ability to self-motivate and effectively manage your time.
  • Handle all the responsibilities that come with running a one-person show. If you’re working remotely for a company, this might mean adding a few administrative tasks to your daily repertoire. If you’re self-employed, you’ll also handle your own bookkeeping, customer service, and marketing.
  • Be okay with lower pay (at least for the first few years). No matter what field you work in, both working remotely and working from home generally means starting off at less pay than performing the same job on-site. Why? Mostly because of steep competition. After all, who wouldn’t want this lifestyle?

Related: How to Figure Out if Working from Home is Right for You

Most importantly, to be successful working from home or working remotely, you need to be passionate about what you’re doing.

Sure, that sounds a little cliché. After all, most everyone aims to spend their days doing something they’re passionate about! The advice to invest in your passions might be even harder to swallow if you feel your current skills are marketable for working remotely, but you can’t see yourself using them long-term.

“But,” you might say, “I’m passionate about traveling!”

Believe it or not, traveling for the sake of traveling gets really tiring a lot faster than you’d think.

Why You Need To Be Passionate About More Than Travel

There are many great, fulfilling reasons to work from home. They may include keeping a schedule that lets you spend more time with your family, living in an affordable area while avoiding a dreadful commute, creating time for hobbies, or simply enjoying working in a more comfortable environment.

What do each of those reasons to work from home have in common?

You’re most likely already familiar with why you value the opportunity to adjust your lifestyle in a way that allows you to prioritize them above the higher earning potential and security of working at a traditional office.

Even if you’re not crystal-clear about all the reasons you want to work from home, it’s still a safer bet than packing up your career and taking it around the world year ‘round. That’s because it’s easy to romanticize the idea of working remotely. If you know anyone who already works remotely, you’ve likely seen photos of them tapping away on their laptops while kicking back on a beautiful beach or in a far-flung locale.

But, the reality of working remotely is often very different from what shows up in pictures.

The Difference Between Vacationing and Working Abroad

Before I set off to work remotely for the first time, I had already traveled enough to fill an entire passport.

I’d started by living abroad as an English teacher in both South Korea and Thailand. After which, I earned extra stripes on my travel-belt by working as a flight attendant for two years. Even then, before setting off to work remotely, I’d made sure to have a healthy, if not slightly rag-tag, assortment of regular clients. (Don’t worry, we’ll make sure you know how in a later installment!) 

Before departing, I’d gone so far as to confirm with my soon-to-be Airbnb host that internet did, indeed, exist at the rental I’d picked to start working remotely. In short, I felt very prepared.

And you know what? That first month was a complete disaster.

Arriving in Bali, Indonesia after an exhausting 27-hour journey, my first fail was realizing it might have been smart to map out the trip to my new home. Not having done so meant that I was surprised by an additional two-hour van ride.

Still, spirits remained high until I arrived at a rental that was disturbingly unlike the pictures I’d seen online: Trash littered the unlit dirt road that connected the rental to the four-building village that was almost a mile away. And any visions of serenity were immediately dashed by heavy construction sounding from the plots of land being developed on either side, despite it being late into the evening.

All of which could have been dealt with until I asked to test the internet—which did not exist.

The landlord had purchased a USB WiFi router from town without realizing not a single service provider offered coverage in such a remote area. Understanding the problem took quite a long time due to a language barrier (my phrasebook didn’t cover setting up utilities), during which I was offered a home-blended juice while troubleshooting the connection.

By the time I’d given into the idea that alternative accommodations had to be found, I’d purchased several SIM cards from a local shop and spent hours attempting alternatives. I’d also failed to make sure my beverage had been made with filtered water (it wasn’t), making that van ride back mighty uncomfortable.

It took almost two weeks of boots-on-the-ground apartment hunting before finding a home that felt safe, was centrally located (lesson learned), and offered an internet connection that was strong enough to work on. That’s almost two whole weeks of practically bleeding money while not earning a dime—not an ideal situation when you’re thousands of miles from home.

Why share with you a story that makes me sound completely inept?

First, I’d like to invite you to chuckle at the boundless optimism that was my believing WiFi could be found in the jungle. More importantly, I’d like to invite you to take a minute and ask yourself what you expect from working remotely.

Do you dream of being productive on a beach, listening to waves while squishing sand between your toes? The reality is that working on a beach is way too hot, there’s nowhere to recharge your battery, and the sand will destroy your laptop in a matter of days.

What about exploring ancient ruins during a mid-day break? While totally possible on weekends, places like Angkor Wat don’t offer WiFi.

It’s important to be equally, if not more, passionate about your ‘work’ and not just the ‘remotely’ part.

Bottom line, working remotely shares many advantages with working from home. Plus, it allows you the opportunity to see some amazing places during your free time, build and maintain friendships around the world, and experience other cultures in a way that’s impossible to do during a two-week vacation.

However, also like working from home, working remotely involves building a marketable set of skills—sometimes an entire business. You might even have to do so from scratch! And that’s why it’s important to be equally, if not more, passionate about your ‘work’ and not just the ‘remotely’ part.

Working Remotely vs. Achieving Location Independence

Earlier, I’d mentioned the phrase ‘digital nomad,’ which is what those who work remotely commonly call themselves. There are so many different types of digital nomads, it’s difficult to come up with just one description. However, those who work remotely and travel tend to have a few things in common: They spend at least a few months of the year abroad, they change destinations frequently, and earn a living while working online.

One thing that’s important to note is that the terms ‘digital nomad’ and ‘location independent’ often get used interchangeably, but there’s a pretty big difference. The reality is that most individuals who work remotely don’t make enough to live and work anywhere in the world.

While you can enjoy a great quality of life working remotely for less than $1000 a month, you will be restricted to low cost of living countries in Southeast Asia or South America. However, you’ll need to earn much more than that to become completely location independent, running your business from places like London, Munich, or San Francisco.

Bottom Line, Working From Home Can Be a Great First Step

Everyone reading this post is in a unique position, with different responsibilities and work experience. If you’re just starting to learn about working online, don’t despair!

Already having a basic knowledge of how to work a Microsoft Office or iWork, plus polishing up your typing skills, can allow you to work remotely in just a few months. It’s even better if you have previous experience in other fields to give you a leg up in niche industries.

The biggest challenge ahead isn’t learning a particular skill set, but fighting the doubt that you might be wasting your time by choosing incorrectly.

Funnily enough, learning to stay motivated through self-doubt is likely the greatest skill you can master to be successful working remotely. For that reason, no matter how hot your heels, consider building your remote-working career from the comfort of your home, even if it means several months of double-timing during evenings and weekends, before moving to a remote location.

By giving yourself ample months to build a steady stream of work, client relationships, and all-important emergency savings, you’ll be better prepared to deal with the pitfalls of working remotely before facing additional challenges posed by remote locations.

Next up, we’ll explore which jobs, skills, and resources allow you to work from anywhere.

Other articles in this series:


Autumn Yates

Autumn draws from a reporting background and years of experience working remotely, while living abroad, to focus on topics in travel, beauty, and online safety.


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