“But how do you make a living? Are you retired?”
I wish I was retired! No. I’ll probably be working in some sense of the word until I keel over. I can only hope that I am enjoying it as thoroughly in twenty years as I am now. Truth be told, even in retirement I would still be writing—just for myself.
My ability to pick up and move to Portugal is based on the fact that I can work anywhere with wifi. My company is US-based; I just happen to be in a different country.

I am a freelancer. You can gussy it up anyway you want—consultant, entrepreneur, editor, publisher—but at the end of the day, I’m skills, experience, and brainpower for hire. I started out as a writer and editor and moved into self-publishing and marketing with books. My niche has always been nonfiction, mostly business books of some sort or the other.
I’ve been in this business for over 15 years which gives me some credibility when it comes to proving I can support myself. The fact that I am self-employed gives me time and geographical freedom. It is largely the reason why I was able to move abroad.
It’s Not About Me
But that’s not really what you care about. Because when people ask me how I make a living as an expat, they are really asking how they can make a living if they become an expat.
Some people already have remote jobs—they work from home and their employer may or may not care if they are based in the same country. Moving countries for these people would be less about how to make a living and more about finding good schools for their kids, perhaps a job for their spouse, and figuring out taxes and health care.
For those who don’t have that, it’s about making a comprehensive and realistic evaluation of your skills and experience and asking if you are expert enough in any area that you can create a living doing it. Writers, graphic artists, programmers, editors of all stripes, etc. can easily find work in the gig economy. Sites like Freelancer, Upwork, Indeed, and many, many others provide a platform where you can create a profile and find jobs.
If you’re in fields that are “hands on,” that is you need to be physically present to do your work, you may have to be re-licensed in whatever country you choose to live in. Physicians, dentists, massage therapists, hair stylists certainly have transferable skills. Working in a new country may require taking classes or board exams again, and/or working under another professional for a period of time. There are multiple services that actively recruit qualified medical professionals to work abroad.
Other businesses may not be fully virtual but you could create an online version of what you do. Many people “drop off” documentation to their accountant but more and more are sending electronic files. I haven’t bought car insurance in person since the 1990s. Many sales and consulting jobs can be handled online. While training sessions may be better conducted in person, they can also be conducted virtually, usually at a lower cost to the client because travel expenses aren’t involved. So, you may be able to adapt what you do to a virtual platform or some hybrid version of it.
Time Zones, Shipping, and Customs
The hardest part of working virtually for me is dealing with the time difference. For most of my work, I can schedule mid to late afternoon calls for people in the US. I tried to work with a VA company based out of Australia and the time zone difference made it more trouble than it was worth. It can be done, but inconvenient meeting times will be the rule, not the exception.
I am fortunate that my particular line of work does not involve shipping hard products. I had a document shipped via DHL from Florida to Albufeira and it ran about $75. Granted, I received it within the week, but it was still pricey. It was also held up in customs, even though it was a document sent in a flat envelope. This may not happen in every country, but I had to supply my Portuguese tax number in order to get the envelope released.
If you make a living hand-whittling and selling duck decoys, you will most likely want to sell them within whatever country you are living. Shipping costs, in or out of countries add up. That’s why expats bring nearly empty suitcases back to the States and return to their new country with full bags. There are certain things you can’t find (yes, I’m looking at you Twizzlers and Peet’s Coffee) in some countries and the item value doesn’t warrant paying shipping and import fees. The same goes for shipping from wherever you end up.
As a consultant and writer, I don’t bump into these issues. I have a friend who sends out thank you cards for me (and does a much better job than I ever could) and navigates my mail. All other work is delivered electronically. If you sell a hard product you could look into drop shipping or creating an electronic version of what you sell.
Teaching English Abroad
Before moving to Portugal, I subscribed to a magazine on expat living, which shall remain nameless. It was mainly a vehicle for pitching not-so-great real estate deals and convincing people they could supplement their retirements by teaching English. We’ll skip the real estate for now.
Yes, you can make a living teaching English in a foreign country. But there are a lot of scams out there, starting with worthless certification companies that will cost you money to fronts for white slavery that can cost you your life. Investigate thoroughly.
Most places will want you to have at least a Bachelor’s degree, but it doesn’t necessarily have to be an English, linguistics, or education degree. You don’t always need teaching experience, though you do need good communication skills. Surprisingly, you don’t always need to be bilingual to teach abroad.
You also will do better with some sort of certification in English as a second language. You can get private tutoring gigs without it, but it’s much better to be certified. The certification you’re looking for is either TESOL (Teaching English to Speakers of Other Languages) or CELTA (Certificate in Teaching English to Speakers of Other Languages—the acronym loses something in the translation). These are more expensive and time intensive than the basic TEFL (Teach English as a Second/Foreign Language). Expect a time commitment of about 150 hours. I have seen accreditation courses range from about $250 to $500. One expat paid over $1,200 for the CELTA certification only to figure out that she would earn about $5 an hour when she included prep time for classes. I have seen others say they make $15 to $25 an hour. Shop around, both for certification programs and job opportunities.
How much you can earn will vary according to what country and what type of teaching environment you are in. Some of the highest paying countries are Saudi Arabia and the United Arab Republic. Generally speaking, Asian countries pay more than European countries. Some places offer housing or housing subsidies as part of the package. Some will cover airfare. These are usually contract jobs and you should have the contract reviewed by a competent attorney.
You may end up teaching privately or teaching at a school. Online instruction has become a popular option. Most of the certification providers have job/opportunity boards. There are jobs to be had, especially if you are flexible as to where you want to travel and how much you need to make.
Teaching English is a viable earnings option, but it is also a matter of supply and demand. Many expats think they can put out a shingle and teach. But because so many people do it, you need to think about how you would structure your classes. You might need to invest in more advanced linguistic training. Having a working knowledge of your host country’s language while not required, may be necessary in actual practice.
Starting Your Own Business
A friend jokingly asked me if I would be buying a bed and breakfast as “all the expats do.” Given that I am an introvert and the B and B would end up being way too similar to Fawlty Towers, that’s a hard pass for me.
I cannot go in-depth on this because it’s a whole ‘nother kettle of fish. Many expats start businesses in their new countries, from restaurants to guest houses to shops of whatever sort. If you are moving to a country with the idea of investing large sums of money (which is what starting a business usually requires), you could qualify for a Golden Visa—automatic citizenship based on investing a minimum yet large amount of cash. Most countries have a Golden Visa program.
If you are going to start or buy a business in your new country, I highly recommend that you already have experience in that particular industry and that you take the time to study the culture and structure of business. In Portugal, you will need a qualified attorney and accountant to help you navigate the waters; you don’t just go down to the local city hall and get a business license.
At this point, I have made a conscious decision to keep all my money-making activities stateside. While I could probably find clients here, most of the expats are retired or semi-retired and really not in need of my services. The licensing and tax implications that would come with the first Portugal-based client would not be worth the paperwork. That could change as I get more familiar with the terrain.
The Reality
I spent much too much time on the Teaching English section; it’s the first thing that most people think to do to make money and it’s one of the most likely places that you will be scammed or at least disappointed.
For most expats, working abroad will come down to freelancing, no matter what particular work you end up actually doing. People who become expats are the types who don’t want to be tied down, whether it is to a country or an office. But freelancing isn’t for everyone.
You need to be a bit of a risk-taker, at least at first. I recommend building up a freelancing business (it can start as a side hustle) before moving to make sure that you can support yourself. Freelancing is often feast or famine; you want to show a steady baseline income both to yourself and to your future country’s immigration department when you apply for residency.
Whether that business is built from getting gigs off job boards or building up a clientele (or a mix of the two) is up to you. If anything good has come out of the pandemic, it’s that more people are now accustomed to working with people virtually, from online therapy sessions to group coaching to one-on-one interactions.
I was meeting clients in Zoom rooms long before COVID hit. It was a bit unusual at the start (though I immediately preferred it to Skype) but now people are familiar with the technology. Even people who are geographically close will be happy to meet virtually because it saves getting in the car, spending time on a commute, and putting on pants. The meetings themselves can be shorter. With virtual backgrounds, you don’t even have to clean up your office/kitchen table.
Earning money in a foreign country can trigger taxes in your home country. Tax law shifts constantly. You may not earn enough to have to pay US income tax on foreign earnings, but you may still have to report it. Consult a competent, licensed professional on this.
You Can Do This
The transition is easier for some people than for others, of course. If you want to live abroad and still need to make a living, there are plenty of ways to do so. You can work remotely for a company. You can build up a business or do gig work. You can get a job in the country you are moving to. The fact that I already had a virtual business made it easier for me to make the move. It also affected the type of visa I applied for and what documentation I needed to show in order to receive my residency visa. The requirements vary according to your personal situation (savings and investments, retirement, minor children, etc.) and the country you want to move to. It’s a matter of working out how to do it. People do it every day. You can, too.

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As always, great stuff Barb! Redhead and I hope to travel more in the coming years and visiting you in Portugal would be cool. I’m scheming a way to make $$ from anywhere as long as I have access to the financial markets and strong WiFi connection. That said, a trip abroad could last longer than the obligatory 2 weeks that most people do. Time will tell.
I would LOVE LOVE LOVE to see you two over here.