5 Biggest Challenges of Being a Digital Nomad

Being a digital nomad has a lot of perks – the freedom to live wherever you want, work whenever you please, and living a life full of travel and new adventures while still earning a living. And it’s becoming more and more popular.

But for all the wonderful benefits this lifestyle brings, it also has difficulties. Here are five of the biggest challenges of being a digital nomad that I’ve found in the past three years and counting on the road. 

5. Living out of a suitcase

Living with only the possessions you can take on a plane sounds very freeing and minimalist – only the essentials! Keep what really matters! You don’t need all that stuff anyways! And you know what – that’s partly true.

Most people have way too much stuff, and sometimes it drags them down or keeps them from living the life they really want. (Getting rid of almost everything I owned to travel the world for a year was very freeing.) 

But you know what’s also true? Some stuff is really great. And you can’t take it all with you on the road. I miss my books most of all – as a huge bookworm, I have dozens of my very favorite ones stored in my friend Emily’s eaves until I have a place of my own to put them. And I’ve got a list of at least 50 books I also want to buy when that place to put them happens.

It’s a sickness, sure – both sets of my grandparents are the same way, as is my dad – but you just can’t cart around dozens of even the slimmest paperbacks when you travel as a digital nomad with just a tiny backpack

I also miss clothes. Mostly I miss having more than three outfits, and having clothes that are just the slightest bit impractical. There’s no room for them in my pack, so it’s a sacrifice I’ve had to make when becoming a digital nomad. Someday I will own high heels again! 

Don’t Miss: Digital Nomad Gear Essentials

sunset over the Adriatic Sea in Split, Croatia during winter
Summer in Croatia means you mostly just need a swimsuit, though.

4. Making (and keeping) friends

This is both a perk and a peril of being a digital nomad. It’s really easy to make friends in most cities as a nomad and expat – Facebook groups and coworking spaces make it almost effortless even for a shy bean like me. 

And I’ve found that I have so much in common with most of the people I meet out on the road – we’re already living very similar lifestyles and are almost all obsessed with travel and new experiences and open to different perspectives. It’s much easier to find new friends with whom I feel a strong connection out here abroad with people who have chosen the same kind of life that I live. 

But that’s also a downside – you get close with fascinating people very fast, and then by the nature of the lives we lead, someone departs the country and you have yet another person in your life to miss. You can always meet up with them again somewhere down the line, but it’s still a fast-moving and furious bonding and parting experience.

Nomad living has big highs and some difficult lows as well. And let’s not even get into dating as a digital nomad, which is an even more intense version of all of this.  

a group of digital nomads and local in Split, Croatia at Matejuska pier
Making new friends in Split, Croatia even during 2020!

3. Visa laws and restrictions

Ask any digital nomad about the stress of the Schengen Zone and you’ll get a lot of sighs. Same thing with visa runs in Thailand and Bali, and the questions every border control official asks you in almost any country. Since nomads move around a lot and tend not to have one single base, you need to find a new country to move to about every three months, depending on where you’re based and what passport(s) you hold. 

I have an American passport, and so I can only spend 90 days in most of the EU and then I have to leave for another 90 days. That means I can’t do three months in Greece and another three months in Portugal right after – I need to find a non-Schengen country to hit up for those following three months. You can read all about how I manage to legally stay in Europe for more than 90 days – it’s not easy. 

Most days, I have an exact mental map of the Schengen Zone in my mind and the Schengen Zone calculator open on my browser. I’m very lucky to have a US passport, which lets me travel visa-free to most places as long as I’m “on holiday” because working as a digital nomad abroad is a bit of a legal grey area. But it’s a constant pressure to count your days and plan your next stop. 

Want to stay longer in a country with one of those new digital nomad visas? Still not without its headaches. In 2021 I was applying for temporary residency in Croatia and… whew. That gave me a lot of agita. My application for the Greek digital nomad visa was also quite a struggle – countries have a lot of work to do to make these applications easier and more appealing.

Related: How Find Housing, Pay Taxes, Get Insurance and More: The Basics of the Digital Nomad Lifestyle You Need to Know

2. Balancing work and travel 

Think that becoming a digital nomad is all about lazy days on the beach and afternoons drinking wine in chic cafes? Sure, that happens sometimes – but not most days. Depending on what kind of digital nomad job you have, you still have to do plenty of work just like you did back in your home city. This is even more true for nomads who are remote full-time employees for a company and so have to keep regular business hours. 

As a freelance writer, I have more flexibility because I set my own hours and I have only 1-2 meetings per week. But I still have a list of deadlines and tasks to do every week, and if I don’t do them, I don’t get paid. Also my clients get mad.

So I’ve had to figure out how to work and travel at the same time – I do a lot more fun stuff on weekends just like I used to with a full-time corporate job. I’m not usually off spending a whole Tuesday at a museum anymore like I did when I was traveling full-time

In fact, that’s why I spend more time in destinations these days. Since my weekdays are typically filled mostly with work (and some social coffee hours because that’s how I do), I need extra time to get to know a city better and see all the sights.

I like this way of traveling anyhow because I get to know the rhythms and people in a place more deeply, but if you think you’re going to travel to a new country every week and still get your work done, you’re either an insanely focused person or about to burn out really fast. 

Related: How I Became a Digital Nomad and What I Would Do Differently

1. Lacking a sense of stability

And the most difficult thing I’ve found about being a digital nomad? It’s a very changeable and unstable way of life. This is exciting and adventurous for sure – moving between countries several times a year, learning to speak new languages and making new friends and learning where you can and cannot buy proper American bacon. 

But it also gets tiring and lonely sometimes, especially if you’re a person who thrives on stability. I have a love of novelty which is why I live like this, but I’ve also had to work harder at creating routines to keep some semblance of stability in my life. But in the tougher times (hello Covid), the lack of a place to call home and your own bed and a quick trip to see your family and oldest friends can be exhausting. 

This isn’t a reason to not become a digital nomad – but it’s certainly something to think about if you’re considering the lifestyle. Finding a sense of grounding in small things – for me, it’s my yoga mat and my silk pillowcase and my writing – is vital. 

And I do like housesitting from time to time to get the feeling of home, even if it’s someone else’s (and some cat cuddles into the bargain, along with free rent).

a solo female digital nomad and stray cat perched on her shoulder in Split, Croatia
And cats – I miss having a cat!

What You Need to Know About Being a Digital Nomad

I’m not sharing all these sad, stressful situations to bum you out or throw myself a pity party or warn you away from becoming a digital nomad. I truly love living like this, and I don’t see myself going back to living in one place and having one job for a very long time. 

But if you’re just browsing Instagram to get a sense of digital nomad life, sometimes it seems like all benefits and no downsides – and that’s not true, just as it’s not true for any one way of living.

There’s so much more to being a digital nomad than propping up your laptop on the beach for an hour and then jaunting off to explore a new city – sometimes you’re up late on a Friday night frantically trying to complete a last-minute client assignment while everyone else parties. 

Decide for yourself if the tradeoffs are worth it. For me, and for so many others, they are. If life as a digital nomad is for you, maybe I’ll see you out there on the road someday! 

2023 update: I’ve actually given up the digital nomad life and moved to Athens, Greece!

More Digital Nomad Lifestyle Resources

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