Imagine spending a month in a villa above Lake Como. You work in the morning and spend the afternoon by the water. For a lot of people, this is a real way to work, not just a dream. But to make it happen, you need more than a job that says “remote.”
Here’s how to do it, step by step.
Many remote jobs only let you work from one country. The company may be happy for you to work from home, but it wants that home to be in the same country where it pays its staff. Hiring someone who lives abroad means extra taxes and paperwork, and many companies don’t want to deal with that.
So look for job ads that say “work from anywhere,” or that list the countries you can work from. If the ad doesn’t say, ask the recruiter early on. A job that keeps you in one country won’t get you to Lake Como, no matter how flexible the hours are.
You don’t need a list of “best jobs for travelers.” Just ask yourself two questions about any job you like.
Does the company care about your results or your hours? Writers, designers, programmers, and consultants are usually judged on the work they hand in. That means it doesn’t matter much where they are. Jobs where you must be online at set times, like customer support shifts, are much harder to do from abroad.
Does the company already have staff in other countries? If yes, it already knows how to handle contracts, pay, and time differences. If not, you’d be its first, and that makes it more likely to say no.
Freelancing passes both questions easily, because no one has to approve where you work. The downside is that you have to find your own clients.
When hiring for jobs like this, employers mostly want to know one thing: will you get your work done without a boss nearby? Your resume should answer that clearly.
Use real examples. If you worked with a team in another country, say so and explain how you kept things on track. If you led a project mostly by email or chat, mention it. If you’ve worked from home before, even part-time, list it. It also helps to name apps you’ve used, like Slack, Zoom, or Asana, because it shows you already know how to work with a team you don’t see in person.
If your resume was written for office jobs, the resume builder by MyPerfectResume makes it easy to rearrange it so this experience shows up near the top, instead of getting lost further down.
If you like your job, you may not need a new one. Your boss already knows and trusts you, which gives you a head start.
Keep your request clear and simple. “Can I work from anywhere?” is easy to turn down. “I’d like to work from Lisbon for six weeks in March. I’ll keep my normal hours and join every meeting” is much easier to say yes to. If it goes well, asking for a longer trip next time becomes much easier.
A tourist visa usually doesn’t let you work, even if your employer is back home. That’s why many countries now offer digital nomad visas. These let remote workers stay longer while earning money from a company in another country. Each country has its own rules, and many ask for proof of a minimum income and health insurance.
EY’s digital nomad and remote work guide compares these visas by country. Still, always check the official government website before you apply, since rules can change.
Don’t forget taxes. If you stay in one country for a long time, you may end up owing tax there. A quick chat with a tax advisor before a long trip can save you trouble later.
A beautiful room won’t help much if the Wi-Fi keeps cutting out during calls. Before you book, ask three things: how fast is the internet, is there a real desk and chair, and is it quiet during the day? Many luxury hotels and apartment hotels now offer long-stay deals with proper workspaces, which makes this much easier.
Also think about the time difference. Southern Europe works well if your team is in London or New York. Bali or Thailand can be amazing, but if your coworkers are in the Americas, get ready for late-night calls.
Once you’ve sorted out the job, the paperwork, and a good place to work, the only big question left is where to go first.
