The Challenge of Being a Digital Nomad

They say that life isn't all “sunshine and roses,” and being a digital nomad is no different. It’s time for some real talk: Today we explore the WORST parts of the digital nomad lifestyle.

Hey - nothing's perfect! Even working for yourself while spending your time in a beautiful country far away from modern civilization.

 Photo by  Abbie Bernet  on  Unsplash

Based on a ton of research and a few workshops on why digital nomads succeed and fail, there are a few issues that people consistently report struggling with over the years, myself included.

1) Loneliness  

First and foremost - loneliness is one of the top, most-cited downsides to being a digital nomad. The concept of loneliness is a tricky thing, however, as I touch on in this article: The Paradox of Loneliness in the Digital Nomad Lifestyle.

People are so afraid of being lonely when they become digital nomads, that they sometimes don’t realize that you can feel lonely at any time in life - including when you’re at “home” around old friends, family members, or even a significant other.

On the other hand, it’s possible to experience moments of euphoria and wholeness while traveling alone as a digital nomad. It’s a complex paradox overall that no one seems to have figured out just yet.


That being said, loneliness still happens when you’re a digital nomad. The best way to combat this feeling is to do fulfilling work, make a conscious effort to get involved in your local community, make friends online and offline, and to reach out to friends and family on a regular basis.

 Photo by  Justin Groep  on  Unsplash

2) Dating

Dating really is a complicated topic, so I decided to go far down the rabbit hole in my blog article: "Dating as a Digital Nomad: How to Approach Love in the Laptop Lifestyle."

In all honestly, dating is an issue that can't be ignored. Many people have tried and failed to solve it.

Why is it so hard to fix?

Because of all the reasons that it's hard regardless of your lifestyle, plus the aspect of being transient. There’s not enough time to develop connections with people you meet while traveling, but digital nomads tend to value freedom and travel over the possibility of a relationship.  

Will it be fixed in the future?

I think yes. At some point, we’re bound to reach a critical mass of nomads worldwide and form our own global cloud community, so it won't matter where you live or where you're from. We'll all be able to interact together as if we're living in the same place, and people will find each other. I hope.

3) Work-Life Balance

When you work remotely, whether you're at home or traveling, you do have the ability to set your own schedule. But sometimes that means working too much or making work the center of your life. Just because you can work 12-15 hours per day, doesn't mean you should.

At the same time, working 1 or 2 hours per day also isn't sustainable, which we’ll cover in the next point.

Overall, being a digital nomad is a great opportunity to increase your quality of life, but it can also be a way to form bad habits if you don’t keep yourself accountable.

4) Being Productive and Self-Motivated

Every human being struggles with this area of life, but if you push it too far as a digital nomad, you can go out of business, or go into debt, or both.

You need to be able to sometimes say “no” to the many distractions that come with traveling, socializing, and overcompensating for other “bad” things about being a nomad, like loneliness.

No one is telling you what to do, so you need to tell yourself what to do—and this is hard sometimes.

Stay on top of your finances and schedule! Since you can choose your own environment, make sure it’s setting you up for success.

digital nomad housing

5) Housing

Where housing is concerned, there are way more options today than there were before, but here's the main problem: The global housing market offers 3 types of options:

  • Long-term rentals

  • Vacation rentals, hotels and hostels

  • Buying a property

None of those really make sense for digital nomads, so we had to change that. Luckily, now we have more options, including co-living, house sitting, and new services like Cabin Spacey.

Are these options sustainable? Time will tell. It's a problem, but we're figuring it out little by little, year after year.

6) Never Knowing if You're Doing the Right Thing 🤔

Frankly, this can kind of happen no matter what you do or where you are, but there's just a lot more uncertainty when you're a nomad, because you’re choosing a life path outside the status quo.

Why do we yearn for external validation of what we're doing?

I personally think it’s partially rooted in our structured school system where we get graded based on how well we follow class syllabi and assignment c instructions. As a digital nomad, it's hard to get that kind of feedback, unless you're part of a remote company or team. So many nomads feel like they’re “winging it.”

As an online entrepreneur, a lot of the time you're on your own. So, on one hand, it sucks, but on the other, you figure it out and do the best you can and learn very quickly from your mistakes. I guess, there's your silver lining.

Digital nomads are uncertain about everything, always.

Therefore, it’s not uncommon to hear a nomad wonder:

  • Where should I live?

  • What should I do for work?

  • How do I find clients?

  • And so on..

And whaddayaknow? A few years in, people started saying things like:

  • "The digital nomad lifestyle is unsustainable."

  • "Digital Nomad 2.0 is hard."

  • "Digital nomadism is a scam."

And having many mid- and quarter-life nomadic crises.

I'm here to tell you that yeah, it's a problem. It's also a human condition. But now that I'm DECADES into this lifestyle, having spent half my life in more than 50 different countries, I can say that there's no single long-term solution that works for everyone.

Some people keep traveling, some slow down, some go home, some get married, some become expats, and we just don't have enough data yet to know the long-term repercussions of a nomadic lifestyle.

Your exit strategy is up to you.

digital nomad exit strategy

The main recurring theme is that digital nomads have all the same problems that everyone else has in modern life, except they are typically exacerbated because we are dealing with things in relative isolation.

Digital nomads are leading the way in creating products, services and support for each other. So, if people are struggling with something like a business problem, dating issue, or mental health, eventually nomads create a group—or an app or a product or service or business—to solve that!

So, if you're not careful, all of these things combined can have some pretty scary results, like anxiety, depression and an overall existential crisis.

If digital nomadism is in your blood (and future), make sure to keep this in mind!

So, those are the things on my shit list.

What's on yours? Let me know in the comments!