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15 Essential Questions to Ask Before Becoming a Digital Nomad

by | Last updated Mar 28, 2021

At this stage, you have read quite a bit about the digital nomad lifestyle. You love the idea of being able to travel the world while making money online. You know about the advantages and downsides of the nomadic location-independent life. But before you quit your job and leave on the next plane, make sure that you know exactly what you are getting yourself into. There are a few questions you should ask yourself before becoming a digital nomad. Read on and find out if this lifestyle is the best choice for you and what you should be aware of.

Questions before Becoming a Digital Nomad, Lifestyle Change, Location-Independent

Becoming a Digital Nomad: Important Questions

Check the following questions and take your time to answer them. Think carefully about them and be true to yourself when giving answers.


1. Can you easily adapt to new situations?

Being a digital nomad means you will change countries more or less often. You will have to find new places to live, locations to get your food from, and learn to be productive in different work environments. You will meet new people and make new friends wherever you go.

On the other hand, you also have to say goodbye to those friends again, which is not always easy. Of course, you can stay in contact and meet again but it is still not the same as being with them. The same goes for a comfortable bed or a lovely house.

If you are the type of person who gets easily attached or who struggles with new environments, you will have a harder time becoming a digital nomad. However, you can minimize the impact by traveling slowly and stay longer in one place before moving to the next.


2. Do you have any dependencies?

Leaving your home base is, of course, easier when you are free to go and have no one who relies on your support. Some people may have to take care of their elderly parents or any disabled relatives. If you are in this kind of situation you will have to evaluate carefully how to deal with that situation. Finding an appropriate replacement for you is not always easy.

Another restriction could be children. Maybe you have shared custody with your ex-partner. He or she might not be too happy if you want to travel the world with your kids. Or they have special needs which makes moving to different countries harder.

Other than that, traveling can, in fact, be very beneficial for kids and their development. There are many families out there who prove that it is indeed possible to take your kids with you on your digital nomad adventures, for instance, Where’s Sharon or Digital Nomad With Kids.


3. Are you willing to make sacrifices?

Becoming a digital nomad has many benefits. But there are downsides, too. There are many things you have to leave behind when you give up your home base. The obvious ones would be materialistic things, such as furniture, cars, clothes, or big electronics.

Apart from that, you might also have to give up on your secured income for a while. Many digital nomads need a few months until they are able to generate a stable income, may it be as a freelancer or with their own business.

Relationships are another crucial factor. You have to be ok with the fact that you won’t get to see your family and friends as often as you would like to and will miss out on important events. The author of The Subtle Art Of Not Giving A Fuck, Mark Manson, finds this very hard about becoming a digital nomad, too:

“You meet tons and tons of people from diverse backgrounds, but you never form deep friendships or relationships. And if you do, it’s usually with somebody else who’s nomadic, and they’re always in a different country, so you only see them twice a year.”


4. How much money can you save?

As mentioned before, the beginning of your new digital nomad life can be a bit bumpy. Many people need to live off savings to get along for the first couple of months. Without enough savings, you will risk running out of money soon in case you won’t be able to generate income straight away.

The same goes for debts. I strongly recommend you to pay back your debts before becoming a digital nomad. It is just another risk factor that puts you under pressure and makes the start of your new lifestyle harder.

If you are wondering how much money you should put aside, check out the linked article. It lists all the expenses you have to consider if you want to get along without income for 6 months of being a digital nomad.


5. How are you going to make money?

Maybe the most important question of all. How do you want to make money? Many people tend to think that being a digital nomad is a profession. But it’s not. It’s only a lifestyle. You still need a job, a way of generating income.

Basically you have three options here:

  1. Work as a freelancer and offer your skills to clients.
  2. Be employed with a company and work for them on a remote basis.
  3. Start your own business.

All of these options have benefits and downsides. If you want to learn more about them, read this article that explains the different ways how digital nomads can make money.

Questions before Becoming a Digital Nomad

6. How much work do you want to put into your new job?

Starting your own business, finding clients for freelancing gigs, or scoring a remote position is not always easy. You may have to learn new skills, spend hours researching potential jobs, and send out countless applications. Especially at the beginning of becoming a digital nomad you might have to work long hours. Many newbie nomads work way more than 40 hours to get a foot in the door.

Are you willing and able to put up with all that? If not, you should try to find out if you could do your current job on a remote basis. Talk to your boss and see if there is an option.


7. Do you have enough self-discipline?

Be true to yourself here. Becoming a digital nomad is an independent way of living and working. That means you won’t have a boss sitting in the office behind you making sure you do your work. You can make your own schedule and are responsible for your own productivity.

In addition to this, you are traveling to exciting places. Of course, you want to go out and explore the country and meet new people. It can be hard to find the right balance between work and travel. It takes a lot of self-discipline to get stuff done. Many people struggle with this kind of freedom.

Jemma Porter from the Portugalist knows how real this issue is:

“I wish I’d known that the myth of the 4-hour-workweek isn’t always true. Sometimes I’m so busy I need to work 14 hour days, leaving me very little time to go out and explore the places I’m travelling through.” – Spotahome


8. What are you going to do with your personal belongings?

When you want to become a digital nomad you obviously can’t bring everything with you. A good solution is to sell your car, motorbike, TV or some of your clothes. Alternatively, you could store it with family or friends or rent a storage room somewhere.

If you are renting a house you should also make sure to give notice on time. In case you own a property, decide if you want to sell it or if you want to rent it out. Start organizing it early enough because often there is a lot of paperwork and deadlines involved.


9. Can you live a minimalist life?

As mentioned before, you have to limit the items you bring with you when you become a digital nomad. Many nomads travel with a backpack or a suitcase only and live with whatever fits in there for months and months and sometimes even years. This minimalistic lifestyle is not the right thing for everyone.

Of course, there are other nomads who take more with them than that. But in general, you will most likely have to reduce your personal belongings and live with less than what you are used to. So decide carefully on what you can and can’t live without.


10. Where do you want to keep your residency?

Your residency is a crucial factor when it comes to determining your taxes. Many countries tax you based on where you permanently live. For instance, if you are registered in Germany and have an apartment there, you will most likely have to pay taxes there, even if you travel most of the year.

Other countries will tax you based on where you source your income. For example, if you live in Thailand but make money online, you probably won’t have to pay income taxes because you don’t earn your money within the country.

If you are from the USA, chances are that you will have to pay taxes there anyway, even if you live abroad for many months each year.

Please bear in mind that the whole tax issue is very complex. Check out this article about the Flag Theory that gives you more information about how digital nomads deal with taxes.

Questions before Becoming a Digital Nomad

11. Where do you want to travel to?

I can only recommend staying as flexible as possible in terms of your travel destinations. You will probably have a few countries in mind where you want to go. But being able to decide on the go where to travel to next is usually the best way to do it.

The reason why you should think about this question anyway is of organizational nature. Some countries have strict visa policies and it can take a while to get it granted. Others require you to have certain vaccinations, for example, yellow fever, upon entering.

Another point to consider is the internet. Sure enough, you can travel to a country with a poor WIFI connection. But you shouldn’t necessarily go there when you have plenty of work scheduled or else your employer or clients won’t be too happy about it.


12. How long do you want to spend in each country?

First of all, this is again important for your visa. Many countries give you a 30- or 90-day tourist visa. Visa runs (leaving the country for a day or two and enter it again with a new visa) are not always allowed.

Many newbie digital nomads also tend to move places quite frequently, like every couple of days or weeks. While this might be ok for a while, you will soon get tired of it and lack productivity. Give yourself time to adjust to a new environment. Settle for a few months so you have enough time to explore the region and get your work done without stressing out.


13. What is your preferred travel style?

Do you want to stay in cheap backpackers, go for fancy hotels or find a nice apartment to stay? Do you prefer eating out every day or do you rather want to prepare your own meals? Long-distance buses or flights?

Of course, you can decide this based upon each situation. Just keep in mind that this will have an impact on the money you are going to spend (so you will need more savings) and on your productivity.


14. What will you do if you fail?

Well, first of all, you have to define your goals to be able to know when you have failed. In case something goes wrong or not the way you have planned it, make sure you have a plan b.

Have enough money to book a ticket back to your home country (if that’s where you want to go). Have an emergency plan for where you can stay for a while in case you run out of money (e.g. your family or friends place). And maybe even have a backup plan for how to make money again. Maybe your old boss is willing to take you back?

Think about your options before the worst case happens. That will also take away the pressure to succeed in the first couple of weeks or months.


15. Do you need any help?

Becoming a digital nomad is not always easy. It’s an entire lifestyle change and probably nothing like what you have experienced before. It’s just natural that you have hundreds of questions and are insecure about what is going to happen.

Luckily, there is plenty of information out there today. Many people have gone through this lifestyle change and are able to provide you with helpful advice. Of course, you will find much information on the Digital Nomad Soul blog. Apart from that, there are many other digital nomad blogs where you can get help and guidance.

You can also join Facebook groups, such as Digital Nomads Around the World, Remote Work & Jobs for Digital Nomads, or Female Digital Nomads, where thousands of like-minded people around the world exchange their experiences.

Questions before Becoming a Digital Nomad

Preparation Is The Key

These questions provide a good starting point for further planning and organization processes. The answers can have a significant impact on how you start and live your digital nomad life. Naturally, there is no right or wrong. Everyone will have different answers to these questions. That’s why everyone will have their own definition of their perfect digital nomad life. You need to find out what works best for you and how you can make this lifestyle work for your needs.

Questions before Becoming a Digital Nomad, Lifestyle Change, Location-Independent





Denise Mai

Denise Mai

Founder of Digital Nomad Soul

Hi everyone, thanks for stopping by! My name is Denise and I have been working online for more than 10 years. In the past, I worked as a remote employee and freelancer & managed to build a six-figure online business. I know that many others would love to work from home or work while traveling, too. That’s why I want to share my experience and help you on your way to your remote career!

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