Living and Working Abroad Like a Boss

So, you’re thinking of ditching your sweaty little office job for a sweatier office job in warmer climes…

Or maybe you want to ditch the suit and tie altogether and work on the beach in your sexy Speedos?

The fact is, working abroad can be an enticing option, especially when laptop monkeys can theoretically work anywhere with electricity and Interwebs.

But is it all it’s cracked up to be?

Well, let’s find out. But first, a quick question…

Why Work Abroad?

Is it because you’re sick of your current job and need a change or do you simply fancy experimenting with a new location?

Important questions people, important questions.

This will obviously determine any awkward conversations with your boss and the preliminaries of an international job search.

For argument’s sake, let’s say your current job isn’t actually too soul destroying…

Remote Working in Your Current Role

The great thing about the online revolution is that digital paper pushers can often test the waters with remote working.

The main benefit of steady remote work is the guaranteed income it provides while supping oversized cocktails on the beach. Plus, with a western earning levels, you can often live the life of Riley in cheaper locales.

With many reputable companies jumping on the work-life balance bandwagon and permitted telecommuting, it’s also no longer such a strange phenomenon.

This can provide some handy psychological security when taking the plunge to hand in your resignation and sail into the sunset.

Having been a remote worker for a while myself (in a digital capacity), I can say that it’s quite agreeable.

Obviously, the biggest factor for your company may be making timezones bend to your will without working extremely unsociable hours.

Also, consider whether you have to be around for client pitches or in-person events, which could prove tricky.

Alternatively, you could consider remote working for another company, which brings me to the following…

expatriate in japan

Digital Nomadism

I know digital nomadism can be a trigger term for many, causing fits of scoffing and disdain, such is the media hyperbole around the topic.

Ever since The Four Hour Work Week was birthed, millennials have been fighting the digital nomad deathmatch, clawing over one another to snap their perfect lifestyles.

But, it does provide quite a few options for working abroad.

From setting up your own business to freelancing and even securing steady employment, you can cultivate the ability to be completely location and time independent.

Travel or Work

There’s a common myth about working abroad that it’ll be a fiesta-fuelled experience of bikinis, beaches and cocktails.

And while there can be an element of this, if you’re going abroad to work, unfortunately, you’ll have to…erm…do some work.

Terrible I know.

Obviously, some forms of employment like digital nomadism or part-time English teaching can provide more flexibility to engage in fun activities during normal work hours, but many jobs won’t come with that capacity.

That said, perhaps you prefer more stability, in which case there’s another option…

Working Abroad for a Local Company

Let’s face it – the laptop lifestyle isn’t for everyone.

While it can be an intoxicating thought when you’re commuting to work on a drizzly Monday morning, the reality of the nomadic lifestyle is often very different.

As Mark Manson comments, there’s always a shit sandwich to eat, whatever you do.

So perhaps constant travel isn’t your thang and you’d rather become immersed in one country, working for a local company.

This is eminently do-able, albeit with one important caveat…

It depends on your skills.

I was fortunate. As a physiotherapist by training, working abroad was a practical option, because even though nationalities change, human bodies don’t (or at least they shouldn’t!).

This means that there are injuries to treat in all the lands, making it the perfect borderless job.

So when I was fed up of the UK and wanted a break, I knew that I could likely treat expats wherever I went. I did this in Argentina, Vietnam and China.

So, what can you bring to the old metaphorical table? Let’s look at the options.

Local Organisations

Can you use your existing skill set to apply for local companies?

It’s likely that whatever you do now might be valuable to these organisations. Are you a data analyst, programmer, or writer?

Perhaps there’s a local office for a large multinational in your chosen country? I had friends in China who applied for such jobs while they were already abroad.

Local companies might also have an international audience requiring native English-speaking employees. I even had one friend who walked into local businesses in Beijing offering to build them websites!

As an aside, I’ve discovered you may be luckier holding a degree from a western country…

Strangely, there can be a certain reverence for applicants who’ve attended an English university, for example, even though foreign students tend to work far harder.

Okay, so let’s say you don’t have professional skills to offer. What else can you do?

Alternative Jobs Abroad

English Teaching

These are perhaps some of the most flexible roles you can find, and I already know you can do it because you’re reading this humble little article.

When I took a break from physio, I knew that I’d like to try my hand at English teaching.

My first step was to investigate where you could earn the highest bang for your buck in relation to local living costs.

Even though I was pretty keen on Japan, the expenses looked too high and so eventually I settled on Vietnam.

When I went out there in 2010, teachers were earning an amazing 20-30 USD per hour, with a beer costing a paltry 0.75 USD – as you can imagine, life was excellent.

But, I made a mistake that almost scuppered my whole plan, by not completing the TEFL course before I left. When I turned up in Ho Chi Minh practically out of money, I found that most schools I applied to (understandably) wanted to see my teaching certificate.

Fortunately, I met a Vietnamese man who was setting up an English school in the residential property I wanted to rent. After agreeing to teach evening classes for a reasonable hourly rate, I had my first teaching job!


If you’re committed to having an experience working abroad and fancy something slightly more altruistic, then volunteering might be the perfect option.

There are so many options for eager volunteers that they’d be too numerous to list here, although I would like to recommend one from personal experience.

When I was in South America, I met a fellow traveller who recommended an organisation in the Bolivian jungle where you could volunteer to work with big cats like Pumas and Jaguars.

Whereas we were meant to go together, my companion ended up taking a different route, but by that time, the seed had taken root, and I was desperate to go.

The organisation, called Inti Wara Yassi, is a gem of a place, and apart from getting bitten on the nipple by an angry Puma on one occasion, I would highly suggest checking it out.

I did have to pay a small stipend to live there, but walking and swimming with Pumas and Jaguars in the remote Bolivian jungle was certainly worth it.

In exchange, we were expected to help run the camp, performing cleaning, basic maintenance, and most importantly, animal care.

If bit cats aren’t your thing, there are many other organisations, like WWOOF and HelpX that can connect you with locals and organisations seeking help.

So, as you can see, working for money isn’t always the only option.


Choosing a Country

Choosing where to go can often be a compromise, and will depend largely on what you’re after.

Here are some questions to consider…

  • Do you have a yearning to live in one particular country?
  • Do you want to live in a particular climate?
  • Do you want to be in a digital nomad hub like Chiang Mai or Lisbon?
  • Do you want to be near certain pursuits like diving or skiing?
  • Do you have to be a certain timezone for remote working?
  • Do you need to be earning a certain salary – look at the currency/average local wage/living costs

There are so many considerations.

My personal approach, however, has always been pretty slapdash, mostly involving searching for ‘jobs abroad’ on the Googles and simply deciding whether I liked the sound of the country enough to apply.

Which brings me onto my next, and final point…

Stop Overthinking

Many of my best trips have been the result of little or no planning.

With impromptu excursions and no expectations, you rarely fail to enjoy yourself, or at least emerge with an interesting story.

This certainly works for travelling, but also for working abroad as well. You needn’t have necessarily been to the country before the applying.

Although it obviously helps with pre-trip prep, I’ve found it pretty exciting to enter the unknown with zero preconceptions.

It’s all too easy to fret over every little detail before you embark, and worse, delay for so long that the trip never becomes a reality, life getting in the way.

So, if you’re in a state of analysis paralysis, my recommendation is to just pick a place and go.

Often the pressure of burning your psychological boats and landing on foreign shores without a comprehensive plan is enough to pour some gasoline on the motivational fire.

An added benefit is that you’ll be entirely free to explore opportunities as they arise, taking you in unexpected directions.

And the worst-case scenario?

Instead of working abroad, you come away with a damn-fine travelling experience under your belt.