When visas stopped feeling abstract
I had traveled outside the U.S. before—Europe, Mexico—but those trips were short. Two weeks, maybe a little more. Visas were never something I had to think about. That changed when I decided to move abroad and go to Thailand.
The TEFL school I enrolled in sponsored my visa and walked me through the process. They told me what I needed, where to apply, and what forms to fill out. I followed the steps, paid the fees, and a few weeks later, I had a visa in my passport.
What I remember most clearly is that it came with rules I didn’t fully understand. There was a 90-day period, but there was also another time period that the visa was good for. At the time, I couldn’t quite grasp the difference. I just knew that there were 2 different timelines attached.
Looking back, it was simple: I had a window of time to enter Thailand, and once I arrived, the visa allowed me to stay for 90 days.
This is where things start to feel real
In Thailand, I quickly learned that there wasn’t just one path to a long term visa.
At the time, my options were tied to what I was doing. I had an education visa while I was in the TEFL program. After that, I started hearing about other possibilities—work visas sponsored by a school, retirement visas, different types of long-term stays, ways people were piecing things together.
What stood out to me was how much the rules could change, even while you were there.
While I was in Thailand, they added a health insurance requirement for the retirement visa. The process for verifying income changed too, shifting from something handled through your own consulate to something that had to be approved locally. From what I understand, the income requirements have changed over time as well. And now, they have options for remote workers that didn’t exist when I first arrived.
That was the first time I realized this wasn’t something you learn once and then you’re done. The rules depend on the country, and they evolve.
From what I’ve seen since then, most people settle into one of a few paths. If they’re retired, they often apply for a retirement visa—or go straight to residency if they’re fairly certain about where they want to stay.
But even that varies. In Paraguay, where I am now, residency is straightforward and flexible. Once you have it, you can work or not. It’s one of the easier systems I’ve experienced.
Thailand felt very different. There’s no simple path to permanent residency for most people, and visas tend to be something you have to renew and manage continuously. There are longer-term options if you’re willing to make a significant investment, but for most people, it’s an ongoing process. Even basic requirements, like reporting your address every 90 days, become part of your routine.
There are work visas in most countries, but they’re usually not easy to get, especially later in life. In some places, like Ecuador, a retirement visa can be more flexible and still allow you to work.
It took me a while to understand that there isn’t a single system to learn. There are patterns—but how they apply depends on where you go and how you plan to live once you’re there.
The main visa options for staying abroad long-term
Retirement and income-based visas
From what I’ve seen, this is the most common path for people over 50.
The basic idea is simple. You show that you have enough income—or savings—to support yourself, and in return, the country allows you to stay long term. You’re not competing for a job, and you’re not relying on local systems to support you.
When I was in Thailand, I qualified for a retirement visa because I had alimony income at the time. It wasn’t something I had planned for—I only learned about it from other expats once I was already there.
Getting from one visa to another wasn’t as simple as switching types. My education visa was a single-entry visa, which meant that once I left Thailand, it was no longer valid. So I had to leave the country to void it before I could start the process for a different visa.
I went to Malaysia, intending to apply for the correct visa there. But plans shifted, and I ended up in Kuala Lumpur, where that visa wasn’t issued. At that point, I had already voided my original visa, so I re-entered Thailand on a visa on arrival and completed the process through immigration there in Thailand instead.
None of it was especially complicated, but it wasn’t something I could fully map out ahead of time either.
What I didn’t fully understand at the time was how much these requirements vary—not just from country to country, but in how they affect your day-to-day life once you’re there. The income requirement might sound high or low on paper, but what really matters is how far that money actually goes once you’re living there.
Some countries make this process relatively simple. Others add layers—health insurance requirements, renewals, reporting rules—that turn it into something you have to stay on top of. In places like Ecuador, a retirement visa can be surprisingly flexible and may even allow you to work. In others, like Thailand, the rules are stricter, and even working online can fall into a gray area.
For many people, this path works well if they already have a steady source of income and a good sense of where they want to settle. But it’s not a one-size-fits-all solution, and it’s often not as simple as it first appears.
Teaching English (TEFL) as a pathway
Teaching English is one of the more accessible ways to live abroad, especially in the beginning.
That’s how I first went to Thailand. I enrolled in a TEFL program, and the school sponsored my visa and guided me through the process. At that stage, I wasn’t thinking long term. I just needed a way to get there and stay legally.
My original plan was to teach in a classroom. I had experience and qualifications, including the ability to teach in an international school. But once I was there, I realized—for the second time in my life—that classroom teaching wasn’t the right fit for me.
Around that same time, I started hearing about online ESL teaching. The pay was better, and it offered more flexibility. So I started teaching online and was able to make enough income to live comfortably. But it also meant that a work visa was no longer an option. I needed to find a different visa path.
Where this path works best depends a lot on the country you choose and the kind of lifestyle you want once you’re there.
Digital nomad visas (and the reality of them)
Digital nomad visas are a newer option in many countries. When I first moved abroad, they weren’t common. In places like Thailand, there wasn’t a clear visa that fit someone working online, even though plenty of people were doing it. That created a gray area.
I was working online at the time, and I remember asking around—other expats, even immigration lawyers—whether that counted as “working” in Thailand. No one gave a clear answer. The general sense was that it was tolerated, but not officially addressed.
That uncertainty was part of what eventually pushed me to leave. Since then, a number of countries—including Thailand—have introduced digital nomad visas designed specifically for remote workers.
The requirements can still be restrictive—minimum income levels, proof of employment, limits on how long you can stay. They’re also not always a good fit if you’re just starting an online business and trying to keep your costs low. Most of these visas require consistent income, not something you’re still building. But if they work for you, they are a great option.
Investment visas
Investment visas are another option, though they usually require a larger upfront commitment.
Instead of showing income, these visas are based on putting money into the country—sometimes through real estate, a business, a government program, or simply by depositing a set amount of cash in a local bank.
The amounts can vary quite a bit depending on the country. In some places, it’s relatively accessible. In others, it requires a much larger financial commitment.
In Thailand, for example, there are long-term visa options tied to significant investment. They offer more stability than the standard one-year visas, but they come with a higher barrier to entry.
For some people, this path makes sense if they already plan to buy property or make a larger financial move in a specific country. For others, it’s more than they want to commit—especially early on, before they know if a place is the right fit.
It’s also worth understanding what happens if you want to move that money back out later. Some countries make that easy. Others have restrictions that aren’t obvious at the beginning.
Tourist visas and figuring it out as you go
Another way people stay abroad—at least for a while—is by using tourist visas.
In some countries, that might mean staying for 30, 60, or 90 days and then leaving when your time is up. In others, you can extend your stay or return after a short trip outside the country.
I found myself doing this more than once.
After I left Thailand, I moved between countries every six months. Part of that was intentional. I wasn’t ready to settle in one place, and I didn’t want to establish tax residency anywhere. But part of it was also driven by visa timelines.
In Bulgaria, Mexico, and Peru, I entered on a 90-day visa on arrival. In Peru, I crossed over into Chile for a day and came back in on a new 90-day entry.
That’s what’s commonly called a visa run. It can work, but it’s not always reliable. Many countries have become stricter about it and look at how many times you’ve re-entered. Some have clear limits. Others don’t, and the decision is made when you’re standing at immigration.
If you’ve done it too many times, you can be denied entry—even if your belongings are still in the country. From my point of view, it’s a risk I’m not willing to take.
It can be a viable option if you’re still exploring or not ready to commit to one country. But it also means you’re constantly either leaving, extending, or figuring out a different path.
Common Visas requirements
Health insurance
In some countries, health insurance is required for certain visas.
When I was in Thailand, this wasn’t required for the retirement visa when I first applied. But while I was there, the rules changed and they added a requirement to show proof of coverage. That was my first experience with how quickly requirements can shift—even after you’ve already figured things out.
In other countries, insurance isn’t required for the visa at all.
But even when it’s optional, you still have to figure out what makes sense for you—whether that’s a local plan, international coverage, keeping Medicare, or choosing to go without.
Financial proof and moving money
In most cases, you’ll need to show proof that you can support yourself.
Some countries require proof of income. Others ask for a certain amount of money to be deposited in a local bank account. Sometimes it’s both. The requirements can also vary depending on the type of visa you’re applying for.
For retirement visas, many countries will accept some form of retirement income. What counts as “retirement income” isn’t always the same—it might include Social Security, pensions, 401K distributions, or investment income, depending on the country.
Some places go a step further. In Albania, for example, your retirement income—such as Social Security—has to be deposited directly into a local bank account.
Once you’ve demonstrated that you meet the requirements, the next question is how to actually move and access that money. How do you transfer it? Do you need a local account? How do you get the best exchange rate?
Those details don’t always come up until you’re already in the country, trying to figure it out in real time. It’s worth researching some answers before you leave. Some options need to be handled in your home country.
Where people tend to get stuck
Visas aren’t usually difficult to understand on their own. What makes them hard is how many variables you’re trying to consider at the same time.
You’re comparing visa types, income requirements, how long you’re allowed to stay, and what happens if you want to stay longer. Those pieces don’t always line up in a clean way, especially when they vary from one country to another.
Some people start with a country and then try to fit themselves into whatever visa is available there. Others start with the visa and then look for countries where that path works. Either way, it’s easy to get stuck trying to figure out the “right” approach before taking the next step.
Residency adds another layer. In some countries, you can apply right away. In others, you need to be in the country for a certain amount of time first, or meet specific conditions before you qualify. That timing can affect how you plan your stay if you’re thinking beyond a short-term visa.
Another decision that comes up is whether to handle the process yourself or use an attorney or facilitator. I’ve done both. In some places, it was straightforward enough to manage on my own with help from expat groups and immigration offices. In others, like Paraguay, working with a facilitator made the process smoother and took a lot of the stress out of it. It often depends on the country and how complex the process is.
Figuring out which visa fits your situation can take some time. Looking at all of the options at once can make it harder to move forward. I didn’t start with the visa. I started with how I was going to support myself, then chose a country and a TEFL program. The visa came after that.
Not sure if moving abroad is right for you?
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Conclusion
There isn’t one visa you need to understand before you can move forward. You can look at one, understand what it requires, and decide if it fits your situation. If it doesn’t, you move on to the next.
Most of what I learned came that way—one visa at a time, in the country I was already in.
