The Realities of the Digital Nomad Lifestyle

The digital nomad lifestyle looks effortless from the outside, but the moment you try to earn a living while crossing borders, you find out you are juggling two demanding worlds at once. We talk through the difference between “traveling” and “working while traveling” and why that gap is where most people get tripped up, especially when time zones, deadlines, and constant change collide.

We define what being a digital nomad actually means, why remote work exploded after COVID, and how many Americans now work on the move, both inside the US and internationally. From our own experiences working on the road, we get into the unglamorous details that make or break location-independent work: stable routines, reliable internet access, backup plans for power and connectivity, and why moving too fast can turn the dream into nonstop problem-solving.

We also dig into the practical travel planning issues people avoid until they hurt: visa rules that shift by country, longer-stay options, digital nomad visas, tax questions, and what you generally cannot do without proper permits. Then we cover the human realities, including freelancing income swings, loneliness when you cannot build community, career limits from remote-worker bias, and healthcare decisions that follow you back to the United States, including Medicare timing and penalties.

If you enjoyed this episode, be sure to follow the podcast, and if you have a moment, leave a quick review. It really helps more people find us. And if you want to go deeper, you can check out my book, Wherever We May Roam, Finding Your Travel Style, where I walk through all of this in more detail. You can search for it on Amazon in Kindle, paperback, and audiobook, or just use the link on our podcast page. If you have any questions, a topic you would like discussed, or would like to be on our show, email us at jim@jimsantosbooks.com

"Wherever We May Roam: Finding Your Travel Style" is available on audiobook on Amazon, Audible, and other audiobook outlets!

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Transcript

Travel Style And The Big Idea

Jim 0:00

You don't have to quit your life to travel longer. Welcome to Wherever We May Roam, the new phase of the travel to Jim and Rita. This podcast is about discovering your own travel style to explore the world. I'm Jim Santos, and along with my wife Rita, we've spent more than 16 years traveling. Sometimes for a few weeks, sometimes for a few months, and sometimes a whole lot longer. And what we've learned is this: there's no right or wrong way to travel. Some people take extended getaways, some roam part-time, some work from the road, and some make travel a full-time lifestyle. This podcast is about helping you figure out what works for you and how to make it happen in the real world. So whether you're planning your next trip or thinking about something bigger, we're glad you're here. Let's get started. Welcome back everyone to Wherever We May Roam. I'm Jim Santos, and with my lovely wife Rita by my side, our goal is to share with you our 16 plus years of travel experience to help you find your own travel style.

What A Digital Nomad Really Is

Jim 1:11

So far we've talked about the extended getaway and part-time roaming, and today we'll be looking at a fairly new development in travel. Now, if you spend any time looking around online or researching travel, you'll eventually run into the idea of being a digital nomad. You picture people sitting around on a beach with their laptop open, working, maybe ordering a mimosa. Just total freedom. At least that's the image.

Rita 1:35

Right, that's the image.

Jim 1:37

Right. But the reality is that working while traveling is not really the same as traveling. And that's where a lot of people get tripped up. Because the digital nomad lifestyle sounds simple, but it's not. Now we're not talking about people who have been relocated by their employer. Uh we interviewed a couple that were transferred to Poland or have worked around the the world before, but that that's a little bit different.

Rita 2:01

Yeah, because really those corporations really hand feed them their help them with their utilities, their banking, etc. etc. If you're doing digital nomad living, you're doing all of that yourself.

Jim 2:14

Yeah, I mean that's a great way to see part of the world, certainly, if somebody's going to pay you to be there. But that's not what we mean by digital nomad. A digital nomad is someone who earns a living while either living abroad or moving from place to place. Now it can be national, international, or both. And typically they're performing some sort of job that just requires internet access. This has really been growing. Uh COVID had a lot to do with really promoting this particular lifestyle. A lot of people, I think, started working at home.

Rita 2:43

Right.

Jim 2:44

Like we were doing. We were working from home quite a bit. And it's just a small step from there to, well, I can work wherever I have a phone and the internet.

Rita 2:51

Right.

Jim 2:52

Currently the estimate anywhere from 15 to 18 million Americans are digital nomads.

Rita 2:58

I bet it's more.

Jim 3:00

It could be more by now. But uh of that group, uh about sixty to sixty-five percent, say about two-thirds, are domestic traveling. Just something you don't really think about, or they work from home.

Rita 3:11

Right.

Jim 3:11

Some people also work from RVs.

Rita 3:13

True. Traveling around the US.

Jim 3:16

But about thirty-five or forty percent of those are working internationally. So on paper, this really sounds like the best of both worlds, because you're earning money, you're seeing the world. But

Two Full Time Lives At Once

Jim 3:28

what people don't always talk about is that you're really you're trying to do two full-time things at once. I mean, we know from our experiences that travel takes up a lot of your time.

Rita 3:38

Oh, definitely.

Jim 3:39

And there's also this problem like, you know, you go to a new country, you're in this wonderful new culture, everything's exciting around you, but you're working.

Rita 3:47

Right. And you really have to really plan to to be able to do your work.

Jim 3:54

Yeah, especially if you're doing the nomad part, if you're really traveling.

Rita 3:57

Right.

Jim 3:57

It it's certainly much easier if you pick a place where you can stay for six months or a year or more. And we'll talk about uh some ways of doing that in a bit here.

Rita 4:05

Yeah, your time your timing back to the US even matters. You're on a different time zone.

Jim 4:11

Right. And if you're working on a regular schedule on a different time zone and you run into the travel problems that we know can crop up, you might be stuck in a bus station somewhere with very limited internet access and trying to do your job.

Rita 4:24

And tons of noise.

Jim 4:26

Right. This is very different from the part-time roamer when you're a digital nomad, because as we said, your schedule really matters. You really have to have reliable internet, and your environment matters. I mean we talked about being in Italy and checking in with the office, and we're in an internet cafe where people are cheering the soccer game going on.

Rita 4:47

Right. And we were there doing deals. I was doing real estate and you were walking people through computer problems at the same time. Yeah.

Jim 4:56

Another part of the digital no nomad scene here is that a lot of these people tend to be doing freelance jobs.

Rita 5:02

Right.

Jim 5:02

So their income can vary a lot depending on what how much output they're producing and what the market is for them. Now we've seen this firsthand and uh we've talked to a lot of people who lived this lifestyle. As we mentioned before, our early experiences, when we first got together, we had a home in West Virginia, and we had a home on the eastern shore of Maryland on the water. And we were shuttling back and forth between those.

Rita 5:27

With hot spots. I would work in in the car with a hot spot.

Jim 5:31

So uh Rita could work while I was driving.

Rita 5:33

Right.

Jim 5:34

You know, it'd be you just put a bunch of files in the backseat of the car.

Rita 5:38

Right.

Jim 5:38

Or computers.

Rita 5:39

It was a three-hour drive, so I could get a lot of work done.

Jim 5:43

Yeah, we would get a jump on my lunch hour and part of the way there. We worked in New Orleans, worked in Florida, uh, conventioned Italy.

Rita 5:51

Yeah.

Jim 5:51

And when we were living in Ecuador the first few years, uh, I was working there also. And that's that work life balance. That was really not a lot of fun. I mean, it was nice to be making a DC income and living in an Ecuador economy.

Rita 6:06

Right.

Jim 6:07

That part was wonderful, but it was a pretty stressful and pretty full-time job. I was working 40 to 60 hours a week. I remember there were some days that I didn't even get a break to go to the bathroom.

Rita 6:17

Plus plus all of the workarounds you had to do. We had to m make sure we had internet at all times. So we had two internet providers.

Jim 6:26

Two internet providers. I had uh battery backup systems for our electricity, because it would sometimes go out.

Rita 6:32

Yeah, yeah, we are an Ecuador after all. Yeah.

Jim 6:36

Yeah. And I would hear our people partying it at the beach around me. And uh I always thought of it as having it almost.

Rita 6:41

Yeah.

Jim 6:42

You know.

Rita 6:43

Yeah.

Jim 6:43

Living in paradise, but just watching it through the window.

Rita 6:46

Right. And and the and the real thing about it is the and so much initial work has to be done in every location that you're going to go to to continue this work, or your income is affected hugely.

Jim 7:01

Right. So those logistics can be difficult to set up. If you're going from place to place, you need to know what kind of internet access you're going to have when you get there. Now, we've been pretty lucky on our travels. I'd say most of the uh Airbnbs that we stayed at, we haven't really had a problem with the internet.

Rita 7:17

We've always asked, though.

Jim 7:19

Yeah, we always ask to make sure they have it.

Rita 7:20

Right.

Jim 7:21

But it's pretty much standard now.

Rita 7:23

It is. Yeah.

Jim 7:24

You think that everyone has to have some kind of internet access. And we were in some pretty remote places.

Rita 7:29

Right. But that that's been in Europe. I don't know what it would be like in South America. It was good in Mexico. It was good in Mexico.

Jim 7:37

Well, one of the interesting things we found traveling is that a lot of places that people think of as less developed countries actually seem to have better cell phone coverage.

Rita 7:46

Right.

Jim 7:47

Because they didn't have the landline system to upgrade from. So they kind of started out with the cell phones.

Rita 7:54

And the fact that people use the cell phone, like we have laptops or iPads. People use their cell phone for their business.

Jim 8:02

Yeah. Yeah. They're pretty much their entire internet experience is over their cell phone.

Rita 8:06

It's their computer. Which they pretty much are anymore.

Jim 8:12

So with the digital nomad, you you have these two different competing worlds that you have to work with. You have your work life that you have to make sure that you're doing everything uh for their right. And then you also have the general workload that you have just as a traveler.

Rita 8:26

Right.

Jim 8:27

Of making sure you have your logistics set up and making sure you can get from place to place. There are some ways to make that easier.

Visas Stays And Staying Legal

Jim 8:34

There are a few countries like uh Mexico and Costa Rica, you can stay there for up to six months.

Rita 8:40

Without a visa.

Jim 8:41

Just on your US or Canadian passport.

Rita 8:43

Right.

Jim 8:44

Uh Albania will allow U.S. citizens to stay for an entire year.

Rita 8:47

Right.

Jim 8:48

And we've also found that some countries like uh Croatia, if you have a prepaid lease for one year, then you can stay for one year.

Rita 8:55

Right. In the UK, you can stay for sixty uh six months, I think.

Jim 9:00

Yeah, but London also, I think you can stay for an extended amount of time uh for that. But again, this varies from country to country. I remember in in Ecuador you could stay for three months, but you could apply for a three-month extension.

Rita 9:11

That's right.

Jim 9:12

So the problem is that it's a shifting playing field. The visa world is always changing. So you really have to s keep up with that, uh, especially when your livelihood depends on it. I mean, when we're traveling, if there's some problem, we can just go to a different country.

Rita 9:26

Right. And if you do have that nomad visa, then you have to worry about where you're going to be taxed.

Jim 9:32

Yeah, that's another problem. Some some people try to get around it by uh applying for a work visa. And some countries do have digital nomad work visas that you can apply for. But the rules vary on that. There may be certain hoops you have to jump through to get that visa. It may have to be renewed at certain intervals, and you may be required to pay taxes on the income that you make there.

Rita 9:55

Right.

Jim 9:56

One thing you're pretty universally not allowed to do is make money from local residents. If you're doing some sort of business that people locally are paying for, then you're going to have to file for a business permit, you're going to have to pay taxes in that country, and it's a lot more hoops that you're going to have to jump to for that. Another uh workaround country uh that we've talked to people about is uh actually Argentina. I've talked to some people in Buenos Aires who have a fairly liberal visa policy.

Rita 10:27

Yeah, it's and it's an ex it's inexpensive to live there.

Jim 10:30

Yeah, it's fairly inexpensive to live uh in in parts of the city. There are more expensive parts and cheaper parts. But because the US dollar is so strong compared to uh their currency, you can often work pretty decent deals there.

Rita 10:42

It's one of our favorite cities too.

Jim 10:44

Yeah, beautiful city, wonderful place to live. And their policy is that you have the the usual ninety days on your passport. But if you take the old Buki Boo, which is the shuttle service across the Rio de la Plata, over to Montevideo in Uruguay and spend the weekend, and then come back to Buenos Aires, your passport gets stamped again, and now you've got another ninety days.

Rita 11:05

You get a reset. Yeah.

Jim 11:06

Yeah. So they're they're pretty liberal about that. And we've been told that even if you don't do that, the fine for overstaying your visa is like twenty dollars.

Rita 11:15

Yeah, it's small.

Jim 11:16

Yeah. So there are people who just don't worry about it. If I ever have to leave, I'll pay the twenty bucks. But I really don't recommend that because again, these things can change overnight.

Rita 11:25

Aaron Powell Right. And we absolutely do what we're supposed to do.

Jim 11:28

Yeah, it's it's definitely a good idea to stay on the right side of the law when you're talking about visas and following laws in other countries.

Rita 11:37

Aaron Ross Powell Yeah. You are not a citizen there and you do not count.

Jim 11:40

Right. You're not going to get any kind of special treatment. No. In fact, it might be quite the opposite.

Rita 11:44

Yeah, it might be bad.

Jim 11:47

Right. Yeah. So there are some definite downsides to it. I mean, the upside, especially for younger people, it's a great way to see the world. It's a great way to get around and explore other cultures, and maybe even pick a place that you may want to eventually stay for longer term. But the downside is, as I say, most of these people are freelancing, so their

Loneliness Career Limits And Remote Bias

Jim 12:10

income is going to vary.

Rita 12:11

Right.

Jim 12:12

There also can be feelings of loneliness, especially for uh younger people who are doing this solo.

Rita 12:17

Yeah, I could see where that could be a problem, especially if there was a language barrier. Trevor Burrus, Jr.

Jim 12:22

Yeah, and and you may not be in one location long enough to make a lot of friends. That's true. And then you're suddenly moving to another place.

Rita 12:28

Right.

Jim 12:29

Then there's that work-life balance that we were talking about. It can be difficult to feel like you're really enjoying either experience because you're trying to do two things at once.

Rita 12:38

Right.

Jim 12:39

We mentioned the logistics. You have to make sure you have internet, you have to make sure you have electricity. You've got to have all of your ducks in a row every time you change location.

Rita 12:47

Yeah, it's not like you're traveling. You are traveling, but you you're traveling to work. You know, to make a living.

Jim 12:56

I ran into this when I was well, I was working for General Dynamics doing tech support for the Senate. And because I was supporting state offices, it really didn't matter where I was. It didn't have to be in DC. So for a long time, Rita and I were uh moving around in the U.S. going back and forth to those two homes, and I was just working remotely on these state offices. But there is a definite bias in a lot of companies for people who are working off-site. Even though studies have shown that people who work remotely tend to stay at a company longer, tend to take fewer sick days, and tend to be more productive.

Rita 13:30

And spend more time at the job.

Jim 13:32

Spend more time at the job, yeah. In fact, in our situation, there were there were two of us uh working remotely, and we realized once that we were doing about 75 to 80 percent of the work.

Rita 13:43

And there were 20 people.

Jim 13:45

Yeah, there were twenty so people doing this, and we were doing most of the work because we were there all the time and we were working. But there's still this bias that you're not a company person. So it can limit your growth in a company like that. And then of course there's uh issues like health care and insurance.

Rita 14:01

Right.

Jim 14:02

If you're working freelance, then you're gonna be paying for these yourselves, and usually paying a much higher rate than if you were going through a company or something like that.

Rita 14:10

How about when we were when we were in Ecuador, we had our own insurance and it was just two hundred and some a month or something. It was not all that much.

Jim 14:19

Yeah, of course, insurance and things like that, healthcare are gonna vary in a lot of places.

Rita 14:23

They are.

Jim 14:24

Some countries, like when we were in England or in the UK, you were able to get health care and not pay for it at all.

Rita 14:31

Yeah, we were so shocked because we were ready to pay because I had had x-rays.

Jim 14:35

When we were in Latvia, nine days in a hospital

Healthcare Abroad And Medicare Traps

Jim 14:38

cost less than three thousand dollars.

Rita 14:39

I know.

Jim 14:40

In Ecuador, we both had surgery there.

Rita 14:43

It was minor I mean. Not minor surgery, but uh it was minor cost. I mean, we were surprised. It was less than our co-pays back home.

Jim 14:53

Yeah, so depending on where you're living, that may not be a problem, and of course your age and your health are always factors on that. But if you want to have healthcare coverage when you return to the US, that's where that kind of becomes a problem.

Rita 15:06

Right.

Jim 15:06

If you're not on any major system like that.

Rita 15:09

Right. If you give up your say, like your Medicare, like if you decide you're gonna live overseas and you go and you do it for like six years like we did and we came back, we always paid for our Medicare and our supplemental insurance. We kept them, we kept those. People who don't, they are penalized when they come back. Their cost is is in is increased every year because that's right.

Jim 15:39

And uh we'll talk about this more when we're talking about healthcare and things in general, but there's a weird little thing in in Medicare. If you have Medicare before you go to live outside the country for an extended period of time, no problem. You can keep it. There's there's no problem, it doesn't matter where you live or whether you have an address in the U.S. still.

Rita 15:56

Right.

Jim 15:57

But if you didn't have Medicare yet and you leave the country, you can't sign up for it unless you have a U.S. address. So you would need to return in order to sign up for Medicare. There's a lot of weird little angles about travel overseas, and really that's a big reason that we we got this book together to try to get some of the practical things that you have to consider when you're looking at traveling overseas.

Rita 16:18

And nothing stays constant. Everything is constantly changing. So what you've heard today from us can be different, but at least gives you a a basis to go off of things that you need to consider when you're thinking about um an overseas venture.

Blending Travel Styles And Next Steps

Jim 16:36

Right. And remember all these different styles of travel we've been talking about, they're not neat little packages.

Rita 16:42

No.

Jim 16:42

Uh a lot of it, there's a lot of bleed over here. Depending on your job. Uh well, my son, for instance, spent six weeks in Japan a couple years ago, but he negotiated with his boss that he would work twenty hours a week online.

Rita 16:55

Right.

Jim 16:56

So he didn't have to take as much vacation time because you know he's a programmer, so he was able to do his work online. You know, we've mentioned when we were traveling, in the US we were still working during the day and we'd go out at night. And even now, while we're traveling, we may be doing podcasts. I might be writing something for international living or other magazines, researching for a book, we're making videos sometimes, be putting presentations together to do online seminars and things of that nature. So there's really not one defining line for each of these. So it's important to keep in mind that you can blend these and you can move from type of style of travel to another type of style of travel.

Rita 17:36

Right.

Jim 17:37

And nothing is really set in stone. That's what we mean about finding your personal travel style. Maybe yours isn't one of these four categories, maybe it's two or three of them.

Rita 17:46

Right.

Jim 17:46

All right, so that's the digital nomad scene. Definitely not for everybody, but definitely something to consider, especially if your job or your profession is something that is portable. Next week we'll be looking at the fourth category, the big one, the big shot that we aimed for, and that's full-time roaming. Get rid of your home base completely and just set out to live a life on the road as a global citizen. So until next time, remember, we travel not to escape life, but so that life does not escape us. If you've been thinking about traveling longer or just traveling better, we hope this episode gave you a few more ideas. Remember, there's no right or wrong way to explore the world. Only the way that works for you. If you enjoyed this episode, be sure to follow the podcast, and if you have a moment, leave a quick review. It really helps more people find us. And if you want to go deeper, you can check out my book, Wherever We May Roam, Finding Your Travel Style, where I walk through all of this in more detail. You can search for it on Amazon in Kindle, paperback, and audiobook, or just use the link on our podcast page. If you have any questions, a topic you would like discussed, or would like to be on our show, email us at jim@jimsantosbooks.com . Thanks for listening, and as always, safe travels wherever you may roam.