The Pros and Cons of Working While You Travel

I’ve been traveling for about 3.5 years now, and I’ve had a job (or jobs) for the majority of that time. Although the jobs themselves have changed over the years, the need to create a balance between work time and travel time has been constant. If you’re thinking of taking your work on the road, here’s a rundown of the advantages and disadvantages you can expect.

Con: Less Time and Motivation to Sightsee

I sometimes feel envious of people on short vacations or long-term travelers living off their savings because they have the freedom to almost literally eat, sleep, and breathe travel. Choosing to work abroad, whether it’s a full-time job or freelancing, means your focus is always going to be split.

It’s impossible for work not to take away at least some of the time and energy I could be spending sightseeing and exploring. I’ve been able to do a ton of both, of course, but not with the unrestrained approach of someone with nothing else to do except travel.

On top of that, in the past, I often didn’t feel the pressure to get out and do as much as possible because I knew I had months or even a year to discover my town. The majority of my local sightseeing ended up being concentrated in my last few weeks or months, when I started to realize that I’d be leaving soon and it was now or never. When you’re working and traveling, not every day is an intense, exciting new experience – sometimes your routine won’t be all that different from your workday routine at home.

Pro: Money

You could easily find thousands – probably even millions – of blogs and articles outlining how to make travel more affordable. These resources are awesome, but for a lot of people, they don’t fully eliminate the fear about what life would be like without a regular paycheck. This is one of the main reasons why I’m such a raving proponent of working abroad: You get all the excitement of traveling and living in a different country, without needing to sacrifice the security of steady income.

You don’t have to watch your savings diminish as the months pass (which is admittedly kind of a scary feeling), and you can put that money towards excursions during your free time. You could even take your adulting level up a notch and pay off any debt you might have – I think most of us know at least one person who spent a year or two teaching English in South Korea after graduation and paid off their student loans completely.

Con: Less Flexibility to Move from Place to Place

Jobs like teaching English or even working in your own field abroad generally mean being tied to living in one city – to, you know, show up for work every day.

The same is true to a certain extent with freelancing because unless you have some superhuman ability to focus anywhere, anytime, having some kind of a routine is necessary in order to get work done. Moving from one city to another means getting acclimatized to a completely new environment. It’s fun, naturally, but finding a place to live, a quiet spot to work, and places to eat or buy groceries all takes time – and time away from freelancing equals less money.

The result is that, for example, although I lived in Thailand for over a year (which included some teaching and some freelancing) I’ve seen less of Southeast Asia than many backpackers who only spent a month or two in the region. I did and saw a lot, and had some amazing experiences, but I definitely didn’t travel as far and wide as people who weren’t working at the same time.

Pro: Cultural Immersion

There’s a reason I write about Thailand and Japan more than any of the other countries I’ve visited – the countries that have had the most profound impact on me are the ones I lived and worked in. I was able to see what everyday life is like in these countries – from how the banks work to how holidays are celebrated. I learned bits of the languages, which allowed me to talk to people I perhaps wouldn’t have been able to connect with otherwise. I think it’s almost impossible to work for months – or especially years – in a foreign country without creating some kind of a life for yourself there; and the experience of having created a life in a country makes me feel like I “get” it in a way that I don’t truly get places I’ve only visited.

Those big moments that many of us are seeking when we travel – feeling fundamentally changed by another country’s culture; or truly recognizing that all people are really the same regardless of our surface-level differences – almost all of these moments happened for me through working in another country, rather than just traveling through it.

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9 thoughts on “The Pros and Cons of Working While You Travel”

  1. I can totally relate to your post, I am travelling and doing freelance web marketing on upwork. Its tough to balance both work and travel, I find when I wake up early in the morning and get it done and out of the way I feel much better for it during the rest of the day and I am more fresh and have more energy in the morning so my quality of work is better.

  2. We’re currently teaching English in China and can definitely see the benefits of work & travel if you are interested in slow travel. This is the first time we have fully immersed ourselves in the culture and even taken the time to learn the language. We agree that during the week there is less flexibility for travel but the weekends we are able to explore as far as the trains will take us! Would recommend it to everyone! To read more about TEFL in China check out our blog:

  3. Totally agree with everything you said. I think there will Pros and Cons to ANY type of travel situation. A Pro to working while travel is that you truly get to immerse yourself in the local culture. You might be more likely to integrate, learn local customs, and assimilate into the unique culture abroad.

    At least, when you work + travel, you are earning money to be able to prolong your experiences abroad. Maybe there’s a good balance, where you work really hard for a couple months, save up and then travel a little more without working? Or maybe find some freelance work online that gives more flexibility? Luckily we live in a world where there are SO many options, it’s just about whats right for each individual! Pretty awesome.

    Thanks for the post!! xx

  4. Oh I agree with all . I have been dojn the same for years now and a while ago discovered . And tried it out in Japan . I think this is a great way to save money when go from place to place . like in between jobs .

  5. I agree 100% with you on the need to find some balance between work and travel.
    Long-term travelling can get tiring and expensive. It’s nice to have a ‘home base’, a routine and a job.
    When working abroad every weekend and afternoon will be an opportunity to travel and explore a new country.
    You are right in saying that you will have less motivation to go sight seeing when living abroad.

    —-However, I think that the opportunity to grow roots and meet the locals is priceless and definitely a lot more rewarding than merely seeing the main sights and taking some nice pictures.

    I lived in Singapore for a year and although I didn’t get around to seeing all the main sights, I don’t regret studying and working abroad at all.

  6. What is it exactly that you do for jobs? Is it all based online? I’d like to travel and work, but I think I’d prefer to work within the community I’m visiting. Any advice on resources for travel related work?

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