7 Challenges Aspiring Digital Nomads Face and How to Overcome Them

The road to becoming a digital nomad is full of many challenges and obstacles. It took us a lot of trial and error to become fully nomadic. Traveling as a digital nomad is completely different from backpacking, the style of travel we’re accustomed to. In order to give you guys a closer look, I’ve invited my friends Carla and Oliver to do a guest post all about digital nomad challenges.


There are many reasons why someone would want a life as a digital nomad. Many of us see it as the perfect way to be location independent and being able to travel the world while earning money from anywhere.

Even though it sounds great, like everything in life, this lifestyle can also have its downsides. And it is not that we are complaining about our life as digital nomads.

To be honest, we are still trying to build up a steady income and are on our way. In the meantime, we are also traveling. We think that it is important for you to know that challenges might come up along the way and we want you to be prepared.

7 Digital Nomad Challenges

1. Working From the Wrong Country

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Yes, being in the wrong country can affect your work. And this doesn’t mean that there is something wrong with the country itself, but some countries might be less suited for digital nomads.

A poor internet connection can be a problem in less developed countries. Sometimes an internet connection is not that easy to find. This, of course, can be horrible for someone who relies on the internet to make money.

Another problem can be that you might go a couple of days without power, which won’t be great if you are working from a computer, or have to send an important email with your dead phone.

The best way to avoid this is to do your research before going on your trip. Make sure the place you are staying has power and internet. Get to know the places you want to visit and plan for the time that you will be out of reach. That way you know when that will be and what you can do before going offline and what you can do afterward. Knowing from the beginning that it is going to happen makes all the difference. The worst thing is when it takes you by surprise.

2. Keeping Your Gear Safe

Life as a digital nomad is great because you can work from anywhere as long as you have an internet connection and of course your laptop or any gear you need for work.

You depend on this gear to be able to work. So you have to make sure that it is always safe, which leads us to our next problem.

Keeping your gear safe might seem easy but when traveling a lot – taking buses, staying in hostels, and being in public places – your valuable things can get lost or stolen faster than you think.

Also, when moving your gear around often from putting it in the backpack, taking it out again, moving it around… it is more likely to fail and break. So it is always important to take as much care of your gear as possible.

That is why always having a look at your belongings is important. When in a hostel make sure to have a lock so you can lock your valuables. While traveling, close your bags and don’t just fall asleep without making sure your things are safe.

Get proper cases and bags for your gear, so that they are protected from rough movements, water, or falls. Make sure you and your belongings travel safely.

We are having this problem right now. My computer is not working the way it should anymore from so much moving around. The battery is failing and it sometimes does whatever it wants. Also, one of our phones broke and we needed to buy a new one. The wi-fi is not working on the other one. With being so far from home and just starting out, it is not easy to just get a new one.

3. You Might Feel Lonely or Need Emotional Support

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Life as a digital nomad is great because you can move as often as you want, travel to as many countries as you want, and meet a lot of people along the way.

But the constant moving also has its downsides. Relationships don’t last for too long, and you might get to a point where you could start to feel lonely. You might be missing real friends and your family.

It is nice to live in a world where technology makes it really easy to communicate but it is not the same as just grabbing a beer with your best friend.

We are lucky in that aspect because traveling as a couple you are at least always with your best friend. The friendships you build might be short, but you have one constant which is your partner.

But if you decided to go on your own, longer stays in one place might be a good option to build longer relationships. Try to find nomad communities and go to digital nomad meetups. You will find people that are like you, and maybe you can even make friends that you can meet in other places.

Since you are able to move as much as you want, you can always go back home when feeling homesick. You can have your home base and travel for periods of time from there. Being a digital nomad doesn’t mean traveling 365 days a year, you can also go back home!

4. It Might Be Hard to Keep Up Your Routine

This is the hardest part for us as first-time digital nomads. Even though you might stay in a country for a long time, you usually still travel around the country. You are in a new place and you want to see as many things as possible.

Taking planes, buses, and trains at different times and with different amounts of days between them makes it hard to build a routine.

You have to get used to the new cities or towns, your new home, and the food. All this is great, but when you have to combine it with work it might get a little hard.

It is important that you set times for work. Sure, you can always move it around a bit depending on the circumstances. But that way, you will more likely plan around those hours, and you will have time to get your work done.

We, for example, try to read, do some exercise and get as much work done as possible before 12. That way we have the rest of the day to enjoy and at night we can work a little more after having enjoyed the day.

5. Balancing a Job and Vacation Time Can Be a Real Struggle

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As we said before, when traveling you also want to get to know the places you visit. But this is hard if you have to combine it with work.

Working is important if you want to keep traveling because without an income it can get hard. So finding that balance between enjoying your vacation and working is crucial.

That is why longer vacations for digital nomads are usually better. That way you have time to do both things while you are in one place. You don’t have to worry about having to take a whole day to work. You can get to know the city slowly in your free time. So try to know beforehand the amount of work that you are going to have. Plan for that or a bit more, so that you are prepared in case anything unexpected happens. If it’s less work, then great! More free time for you.

Divide your work up in a way that will still give you time to enjoy the places you visit. Try to use the working time wisely to get as much done as possible. Work efficiently.

This is still a bit of a struggle for us. We are still getting used to having to work on vacation. The working efficiently part is the worst, though. We seem to take way too long for things that could be done much faster. But I guess, with time it will get better.

6. Keeping Your Finances in Order

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There are many ways to become location independent. Some will do it with freelance jobs, some will do it with a blog and affiliate marketing, some will also sell their own products, or some will have a remote job.

No matter which category you fall into, you have to make sure that the money keeps flowing in.

As a freelancer, you have to constantly be looking for new clients. If you’re lucky, you’ll have your set of fixed clients. Either way, you have to make sure that they are satisfied and want to keep working with you because your salary depends on that.

The same happens as a remote worker; you have to deliver if you want to keep your job. In both cases, your salary depends on others, and you don’t want it to disappear from one day to the next.

With a blog, you can influence it more, with the amount of work you put in, but your income can also change from one day to the other.

So it is always important to keep an eye on your finances and your work because you don’t want your beautiful lifestyle to change all of a sudden.

7. You Never Know What Can Happen

If there’s one great thing about traveling, it’s that it is always full of surprises. Of course, you can turn this around, and those surprises can sometimes turn into nightmares.

When planning a trip you always plan the great things that are going to happen, hoping nothing bad ever does. But we have to be realistic, especially when constantly moving because things can also go wrong.

Your flight might get canceled, your bus might get stranded or your bag might be stolen. All these things will affect your work, and those things need to be considered.

You also have to keep in mind that you might have an 8-hour difference with your boss and that he will be emailing at times that you might not want to talk to him.

Yes, disasters can’t be predicted, and it is hard to be prepared for them. But getting into this lifestyle you need to count them in and be able to act quickly if the situation requires it.


The things listed above are some difficulties that we have found in our time as digital nomads. We want to share them with you so they don’t take you by surprise, like some of them did us.

But, we don’t regret any second of our journey, and we encourage anyone thinking of jumping into the digital nomad world to just try it out. You can always go back to your normal life. If you never try it, you will regret it for the rest of your life!

So hop in, and enjoy the beautiful things the world has to offer and live life like a free bird!

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Bio: We are Carla and Oliver. We left our lives in Berlin to travel and explore the world. We became nomads by doing it and now we are on our way to becoming digital. We believe that everyone should do what they love, and for us, it is easier as digital nomads. 

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