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3 Digital Nomad Challenges No One Ever Talks About

*Disclosure: This post has affiliate links.

By now, you’ve heard of digital nomads. By now, you’ve heard them complain about how lonely it gets, how the constant motion makes them crave stability, and how it’s difficult to maintain relationships while moving around so much.

This post will not talk about any of that.

I’ve been a “digital nomad” since about 2014, meaning I work online and don’t stay in one place for longer than 8 months at a time. And when I travel, I move—as in, I don’t pay rent in the U.S. (where I’m a citizen) while I travel in Hungary.

There are three main challenges of being a digital nomad that I NEVER see anyone talk about. Here they are…

Digital Nomad Challenges no one talks about

#1 Your medical records become a mess—a big problem if you have a chronic illness.

What does that look like exactly? Here’s what’s happened to me most recently:

  • While in California, I realized I had cracked a couple of my teeth (I grind them at night) and needed to go to the dentist.
  • I went to a dentist in Arizona, who then needed my previous dental X-rays—from a dentist in Florida.
  • The Arizona dental office had to get my permission to contact the Florida dental office and obtain my records.
  • The X-rays took a while to come in, but about 2 hours later, they were received via email and the Arizona dentist was able to read them and form a treatment plan for me in Arizona.

Last year, while I was establishing a primary care physician in Florida, she needed my previous health records—from my last doctor in California. This Florida doctor actually scolded me: “You’ve gotta stop moving around. You need to stick with one doctor so they can see your overall health history.”

Yeah, that’d be nice, except I move EVERY FEW MONTHS.

Now, if you are traveling internationally, it’s way worse! While I’m abroad, I try to hold off doctor’s visits until I get back to the States (where I’m a citizen), but if you have a chronic condition, this becomes tricky.

For example, for years, I had GERD (Gastroesophageal Reflux Disease), which is basically chronic acid reflux. Before I flew to Paris for 5 weeks, it flared up terribly. I had to fly out in a few days, but I was faced with potentially having to get an endoscopy (where they stick a camera down your throat and into your stomach).

Thankfully, I didn’t end up doing it, flew to Paris, and my symptoms calmed. BUT if something HAD happened in Paris, such as an ulcer, it would have been a nightmare.

While it’s not the perfect solution, I always travel internationally with travel insurance that covers medical incidents. This is the travel insurance I use.

#2 Filling out any sort of paperwork will become a huge headache.

For a digital nomad, nothing triggers an existential crisis quite like this question: “What is your address?”

Because, what address do you mean? The one I’m sleeping at tonight? The one where most of my stuff is? The one where I’m registered to vote? The one where my business is registered? WHICH ONE?


If I hear ONE more digital nomad say, “I have no address,” I will SCREAM. YOU HAVE TO HAVE AN ADDRESS. It is required by law. You have to have it to apply for a passport. You have to have it to get a driver license. So cut the crap.

Usually, what I have to do is determine the PURPOSE of the question. For example, if I’m at a dental office filling out paperwork, and it asks me what my address is, they probably need to know that for two reasons:

  1. To know where to send any outstanding bills. In this case, I need to make sure the mail goes to my permanent mailing address, which is a UPS Store. I don’t want to give them the address to, say, an Airbnb I’m staying at in Arizona for one month, because they may send me a bill AFTER I check out of that Airbnb, and I’ll never see it.
  2. To match the address to my dental insurance billing address. In my case, it’s the same as my permanent mailing address. If it were different though, I’d need to check with the dental office to make sure they have matching records. Otherwise, billing issues may arise when they submit claims to my dental insurance.

#3 Obtaining credit will be more challenging.

Credit card companies and lenders like to see that you’ve stayed at one fixed address for a long time. It shows stability. And living a digital nomad lifestyle is the OPPOSITE of stability.

Another complication is if you are constantly moving, each time you apply for a credit card, your application will likely get flagged for further investigation. This is often because if you are at a new address, it doesn’t yet show up in your credit history. So they will need proof that you actually live there.

When this happens to me, the credit card issuer has to send me a piece of mail to the address I put on my credit card application. I then have to let them know I received the piece of mail, and tell them what the code was on it. This is to prove I actually do live at the address.

Alternatively, sometimes I just call the credit card company and they don’t need to send me mail! In this case, they just ask personal info questions to verify my identity, and then they approve me on the spot.

Overall, just realize that entering a different address each time you apply for credit will likely slow down your credit approval process.

Digital Nomad Challenges: Worth It in the End?

There you have it! The top digital nomad challenges I wish people had warned me about. I’m still navigating this territory, and I’m sure more information will come out as this way of living becomes more and more popular.

So is it worth it? Dealing with all these hassles when I could have a “normal” life as a non-nomadic person? I don’t know. It’s the life I chose, and I don’t know how long I’ll keep up the digital nomad lifestyle. But for now, I’m enjoying it while I can. I can definitely say I don’t have plans to go back to a desk job.

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Amy is the founder of The Wherever Writer. An avid traveler, she has visited Machu Picchu twice, run across the world’s widest avenue in Buenos Aires, and eaten her fill of gourmet cheeses in Paris.

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