How to Live in Paradise and Still Make Money

To make Wealthtender free for readers, we earn money from advertisers, including financial professionals and firms that pay to be featured. This creates a conflict of interest when we favor their promotion over others. Read our editorial policy and terms of service to learn more. Wealthtender is not a client of these financial services providers.
➡️ Find a Local Advisor | 🎯 Find a Specialist Advisor

We’ve talked before about retiring abroad and the best places to retire to stretch that expat pension, but it’s also possible to stretch your current salary by living somewhere completely different as an expat, as long as you can work remotely.

Just a couple of years ago, that wouldn’t have seemed viable for most of us, but if there’s one positive thing that’s come out of the pandemic, it might be that we’ve all realized that most office-based jobs can be a lot more flexible than we ever imagined. Whether you love remote work or hate it, you may well have discovered it’s more than possible, given the parameters of your current job.

There have always been remote workers living it up in far-flung destinations. Long before the pandemic, the digital nomad lifestyle was a reality for large numbers of freelancers and remote employees. I wrote about some of the great opportunities out there for location-independent workers back in 2018 (of course, that was when frequent worldwide travel was still easily accessible).

Frequent worldwide travel may not be as easy as it once was, but there are ways to go and spend up to a year, or even longer, in various countries that are actively encouraging remote workers. Remote work permits are being referred to in the freelance community as ‘digital nomad visas’ though they’re rarely actually called that.

“Start by considering what countries provide digital nomads, so you don’t fall afoul of the law,” said Jane Mepham, CFP, Founder and Principal Advisor at Elgon Financial Advisors. “Do some research on the locations you are considering. Things like ease movement, health care, internet connectivity, and taxation.”

Thinking you could stretch your current salary or job income by living somewhere totally different? You probably could. Here are a few of the places ready to welcome you.

Bali

The idyllic island of Bali in Indonesia has long attracted the digital nomad tribe, who flocked there on tourist visas and worked from backpacking hostels and coffee shops. In 2021 Bali announced a plan to offer a remote work scheme allowing those working internet-based jobs within the country to stay for up to five years.

Income earned outside the country (via remote work) won’t be taxed in Bali. Ongoing COVID restrictions in Bali do seem to be delaying the implementation of the scheme, but it’s certainly one to keep an eye on, especially given that the cost of living in Bali is significantly lower than in the US.

Costa Rica

This one was on our list of places to stretch those pension dollars as the cost of living is pretty reasonable compared to many places in the US. The Costa Rican government has now announced that a new permit will allow remote workers to stay in the country for up to a year (with the option to extend to another year) while working remotely. Workers won’t have to pay local income taxes.

Numerous Caribbean Countries

Caribbean countries seem to be leading the way with digital nomad type visas, with Barbados, Antigua & Barbuda, The Cayman Islands, and The Bahamas all offering some form of remote work visas for at least a year (often with options to extend), and again, usually without the need to pay local income tax.

The issue with Caribbean countries is, of course, that they tend to be expensive to live in, so may not help you stretch that salary the way you want to. It may be worth investigating your chosen island, though. One reason that ex-pats find living in the Caribbean expensive is that the cost of things like electronic goods and clothing is pretty high. If you’re just there for a year, that might not impact you much, if at all.

Croatia

Croatia is well known in the north of Europe for being a sunny, cheap, southern European vacation destination. The cost of living is very reasonable, and now there’s a short-term residence permit available for digital nomads for up to a year.

Many Americans might be wary of Croatia as it’s not a well-known destination within the US, and obviously, few Americans speak Croatian. It has, however, long been a popular destination for those from the UK and other parts of Northern and Western Europe. In the tourist destinations, you’ll find English is widely spoken, and the online application for the digital nomad permit is available in English.

Portugal

Portugal is another southern European destination known as a fun and affordable vacation spot by those in Northern Europe, and, much like Bali, has been attracting ‘unofficial’ digital nomads for many years partially due to a low cost of living. Again, English is widely spoken in the tourist areas (and a few more Americans probably speak Portuguese, compared to Croatian). The country offers a residence permit for independent workers and entrepreneurs for up to one year. The Portuguese island of Madeira has become a particularly popular destination for remote workers, partially due to the island’s Digital Nomads Village.

Obviously, there’s a lot to think about before deciding if the digital nomad life is for you. You’ll generally have to provide proof of health insurance, income, and sometimes a criminal record check.

While you’ll save money by not paying local income tax, you’ll need to consult your own tax professional about the tax implications of living abroad for a while. You may or may not still be liable for tax in your own country, depending on your circumstances.

“If you’re working for a States-based company, you will still need to file a US tax return,” said Becky Neubauer, Founder of Lifepothesis. “Taxes can be a headache, even if you’re not traveling abroad. So, I recommend hiring a CPA or accounting service to file your taxes for you so that you know they are done correctly. Tax companies, like H&R Block, have excellent online resources for figuring out how to file if you’re living abroad.”

You’ll also have to consider the implications of the worldwide pandemic and how that’s likely to impact travel in the future. If however, you’d like to live in paradise for a while, without sacrificing your income, a digital nomad visa might be just what you’re looking for.