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August 30, 2023 Travel

11 Truths for Older Digital Nomads

Lee Rosen

I've been “traveling-while-working” for many years now. I love it.

In 2015, after sending our youngest off to college and parting with most of our possessions, we embarked on our journey into the unknown. Our first stop was Berlin, where we worked remotely.

From there, we traversed Europe, Asia, Oceania, South, and Central America, and parts of Africa. Our experiences in countries like Namibia, Norway, Jordan, Myanmar, Iraq, India, Vietnam, China, Nicaragua, Ethiopia, and ninety more have left indelible marks on our memories.

But being an 'old' nomad is different from being a 'young' nomad. Age isn’t entirely a state of mind, no matter how much we want it to be. There are real differences between young and old.

Getting older-having already established a career, raised a family, accumulated assets, and developed health concerns-makes us different from many who have blazed the digital nomad trail.

There’s quite a bit written about becoming a “digital nomad.” Some of it is simply informative, and some of it is 'content' meant to inspire you to buy products that will reward you with 'freedom.' It’s all interesting, and I certainly spent considerable time reading/dreaming about life on the road before we set out.

Much of what is written in the digital nomad arena is written by young nomads. These folks are typically in their early twenties to early thirties. They’re eager to dole out advice, but that advice is based, of course, on their experience. Their experience is sometimes limited by their age.

I’m not suggesting that it isn't worth reading the tales of the young nomads. In fact, I found much of it quite helpful. I’ve just learned that there are some issues that the younger nomads can ignore, because they’re young.

Here are some tips for the older digital nomads:

1. It’s not always cheap.

Young nomads love to extol the economic virtues of long-term travel. Some publish their expenses and brag about how they get by on next-to-nothing. That’s awesome for them, but my wife wants us to have our own space--an apartment or decent hotel room, a king-sized bed, air conditioning, and a pool. Call her a princess, but I’m glad she takes that position because I get to blame her while enjoying the creature comforts.

Its true that some parts of the world are less expensive than the more developed countries, but many “Western” style services are pretty expensive in less developed countries. The Mandarin Oriental in Kuala Lumpur is less than the same hotel in New York, but it’s not what I'd call cheap. Some young nomads are content to stay in a hostel dorm room. We’re not.

We tend to eat in the hot restaurants of the moment, buy food in the gourmet grocery stores, and take advantage of services aimed at tourists. (Can you say, “helicopter tour?”) We don't want to visit a cool place and skip out on the tours, sightseeing, and other opportunities available to tourists. Those opportunities always come with a price tag, and you feel pressure to take advantage of your time somewhere new. You don’t have to break the bank, but you probably shouldn't expect to live on a shoestring.

2. Insurance is important.

When you study the published budgets of many nomads, you’ll discover that they don’t include a number of things:

  • health insurance
  •  life insurance
  •  disability insurance
  • renters insurance (required for umbrella)
  • a personal articles floater
  •  non-owner automobile insurance
  • an umbrella liability policy
  • a medical evacuation policy

When most young nomads mention insurance at all, it's an inexpensive travel insurance policy that offers next to zero coverage. Of course, you could pass on the insurance, as many young nomads do, but then you’d risk your assets. That might not be smart. You could also opt for an expat medical plan and save big bucks, but you’d likely be locked into health care in places other than your home country and be subject to underwriting requirements and pre-existing condition limitations.

3. Medical tests aren’t the same everywhere.

Some old nomads, like me, have health issues. I’ve learned that medical tests vary pretty significantly from country to country. Less developed countries simply don’t have the machines and technology required to do certain tests. There’s one test I get that is only offered in the United States and a few other countries. I take the test once a year and have to fly back to get it. Be prepared for that possibility. Young nomads often praise the medical care in other countries, but most of them don't have complicated issues and haven't tested the limits of the healthcare systems in those places.

Even if you have no medical issues, you may prefer to do routine medical tests in a more developed country (if that’s what you’re used to doing). Colonoscopies, pap smears, and mammograms aren’t fun regardless of location, but I suspect they're less fun (and considerably more anxiety producing) in Laos, Iraq, or Algeria (where we’ve recently been traveling).

4. Retirement investment is in real money.

When young digital nomads lowball their expense estimates, it’s often because they aren’t  saving for retirement. Study their budgets, and you’ll realize they're missing that significant line item. Saving for retirement is typically done in your home currency and based on living standards there. Of course, you might plan to retire abroad, but be cognizant of the aforementioned medical test/expenses/insurance issues. If you want to build a retirement plan that gives you options, you may need to devote substantial funds toward investment.

5. Backpacks require strong backs.

Call me a wuss, but my backpack lasted about two weeks before I said, “Screw this!” and bought a Rimowa carry-on bag-one with those fancy spinner wheels. I’m much happier now, gliding my bag through the airport while my back stays sweat-free.

Young nomads extol the virtue of the backpack and explain that it makes them nimble as they crossover unstable terrain on the way to the hostel. I just let the porter carry my bag to the waiting car. Then the doorman carries it into my accommodation. Okay, that may be exaggerating, but I rarely go anywhere that doesn’t allow me to roll my bag.

6. Prescription medications are a hassle.

We're all falling apart. This is true even when we're young; we just don't realize it quite yet. I'm 61 years old, which means I’m falling apart in ways that are readily apparent. I’ve got glasses, and I take four prescriptions (I had a heart attack 25 years ago). My wife takes medication, too. Even with our 'international coverage,' we run into challenges with getting reimbursement from our carrier for medications purchased in other countries. Sometimes the drugs are so cheap that we don't care. But if the medication is expensive or hard to find, then be prepared to jump through some hoops. Mailing drugs is likely not a solution to your issues on this front; that's usually prohibited by mailing regulations.

7. Bargain airfares don't provide a first-class seat.

I’ve flown in the back. It’s fine, but it makes me sore, cranky, and unpleasant---especially if I have to sit there all night. I’d rather fly up in the front in a lie-flat seat with a good meal. Thankfully, we’re able to pay for most of our business/first-class flights using points. But that keeps us from taking advantage of some of the bargains the younger nomads get excited about. Only you know whether you’re willing to be jammed in the back to save money.

It’s one thing to endure economy when you’re traveling a few times a year. It’s something different if a significant part of your new life involves lots of time in an airplane. Of course, there’s no requirement that you fly up front. It’s just one of those things that isn't even mentioned by many of the younger nomads and it might become important to you.

8. You might want to see your kids.

Young nomads typically don’t have kids. You might. And you’re going to want to see them once in a while. Flying them to you is one option. But you may want to go visit them. That needs to be factored into your thinking about how this will play out. Just remember to include that priority in your planning, especially if you like your kids.

9. You won’t be hassled at immigration.

There’s quite a bit of discussion in the nomad universe about the need for onward flight tickets, visas, and proof of employment/assets when passing into a country through immigration. As an older nomad, you’ll tend to be waved right through. Generally, older nomads are viewed as exactly the kind of visitors most countries want. We’re quiet, peaceful, and willing to spend some cash. Don’t be discouraged by the scary stories that some of the young nomads tell about immigration scrutiny. You’ll usually be welcomed with open arms.

Since you've got the financial wherewithal, it makes sense to prioritize time over money. Be sure to enroll in all the time-saving/line-avoiding programs for immigration. Americans are smart to enroll in “Global Entry” for quick entry to the US, Australia, New Zealand, and other countries, and to explore the “APEC Travel Card” for other nations. “Registered Traveler” service makes entry into the United Kingdom faster as well.

10. Long-distance communication is pretty easy.

Many nomads complain about the challenge of staying connected on the road. They’ve got bad internet connections and run into obstacles getting local SIM cards. These issues are mostly financial, and they’re exacerbated by the need to live on a minimal budget. We had great internet in notoriously disconnected Laos and Myanmar when we needed it for calls. Finding the connection simply involves spending more money, and we could easily justify the expense because the connection was needed for lucrative work. Islands, however, are often tough for everyone, even with unlimited piles of cash.

11. Your parents are an issue, too.

There may be times when your parents need your assistance if they're still living. Sometimes those issues may put a crimp in your nomadic lifestyle. Be mentally prepared for that possibility. On the upside, dealing with a parent's health issues or death is something you 'll easily be able to incorporate into your plan, given your ability to work remotely. Of course, these issues are challenging, but being able to easily travel gives you some flexibility that may ultimately make it easier to manage.

In short, there is a great deal of information out there for new digital nomads. You'll find plenty of guidance as you prepare to untether. Hopefully this advice, tailored for the older nomad, will assist you in further thinking about and preparing for your travels.  We look forward to crossing paths with you on the road.

Keep up with our current itinerary and check out our Yearly Digital Nomad Lawyer Updates.

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Lee Rosen

Executive Director | Rosen Institute

Lee Rosen sold Rosen Law Firm in North Carolina in 2017. Since then, he has served as Executive Director of Rosen Institute, helping more than 1,000 law firms succeed.