Top 14 Nomad Challenges You Must Overcome To Be Successful & Happy

While this lifestyle can be amazing, it’s not for everyone.

Thinking about going the location independent route? Getting an overview of the top challenges can help clarify what you are getting yourself into.

Here are a few of the main ones with tips on how to manage — after 5+ years with this lifestyle.

Making Progress Even If Sangria Is Calling

One of the main reasons why many people who say that they want to travel the world while working don’t end up doing so, or aren’t able to sustain this lifestyle long-term, is simply because they don’t develop the discipline that it requires.

Staying productive while you’re surrounded by temptations requires the ability to prioritize, say no, stay focused, and put in the work, even if it’s a perfect day to drink sangria on the beach. After all, you can be based where most days are perfect if you’d like. So ask yourself, would like this to be your life or a short vacation? That perspective often helps me get things done.

>> 10 Tips: How to stay productive while traveling full-time

Figuring Out Important Stuff With No Right Answer

From wanting to stay longer in a country you really enjoy, to insurance, taxes, and reporting on your financial results. The nomad lifestyle has grown significantly over the years, but the traditional systems are still way behind. While you might have citizenship in one country, you could work with clients based in other countries. As you’re finishing those projects, you might travel across 2–3 countries more. This is complex even for experts because tailormade solutions for the nomad lifestyle are still lacking.

While questions about taxes etc. are pouring in across nomads forums, the answer often is “it depends”. Where you come from, where you’re going, and what kind of work you do are all determining factors. Often there is no standard advice, you have to figure out a lot on the way!

>> US Tax Guide for Digital Nomads

Becoming An Expert At “See You Soon” ❤

Besides that you won’t see your friends and family as often, you’ll also end up meeting many new, incredible people. Over time, your favorites will be spread out and you can therefore feel divided. Where should you go to reunite? How to set off time to be able to catch up with everyone? When will cloning myself become possible? 🙄

You’ll also likely miss a few special occasions, like birthdays, Christmas, and so on. You can, however, choose to base yourself anywhere at any time. If you feel homesick, you can always work from your hometown for a few weeks! Even if I go back less frequently these days, I spend more time with my family now than before. Then I used to go home a few quick weekends a year. The time we get together now is more concentrated but of much higher quality!

>> How To Develop And Maintain Meaningful Connections As A Digital Nomad

Learn That You Aren’t As Productive As You Think

When you’re always based in different, gorgeous places, and your normal Tuesday can be as good as someone’s holiday, it’s easy to end up in some kind of in-between-work-and-vacation mode.

Even if you’re based in paradise, it’s still as important to take proper breaks from work to stay productive. Remember that it’s literally impossible to be productive all the time. In general, scientists agree that the ideal daily working time is around 6 hours. If you use your most productive time wisely and take time off in between to do other stuff that makes you happy, you will be surprised over how much you can get done!

As an entrepreneur, work won’t end naturally. Things might blend together, especially if you work from home. So it’s up to you to set the limits.

Always Being New In Town

Moving around a lot means that you constantly have to learn how things work. From where the supermarket is located, to where to work out, areas to avoid, how to meet and approach people, and so on. Nothing teaches you that what you thought was obvious isn’t always, as well as traveling. The way of thinking and doing things can be completely opposite to what you’re used to, which is what makes it so exciting. It’s also a great patience practise! 😉

Always putting yourself into a new place and understanding how it works takes time and energy. Things that would be quick back home will usually take longer in the beginning.

While I’m happy with a relatively fast-paced travel style, it’s not for everyone. Slow down if you need more time to get into a routine where you are able to work and feel good. Remember that you choose your tempo and can make lifestyle changes at any time.

Finding Comfortable Accommodation Can Be a Bit Like Tinder

Wherever you go, you have to find a new place to stay. While it can be fun to mix it up, always searching for alternatives takes time. Just like on Tinder, some places won’t live up to their marketing.

I’ve had mostly great experiences, but it’s good to be aware that it’s not always smooth to find a place where you feel at home. Accommodation costs will also increase when you stay in a place for shorter periods. You’re staying longer than an average tourist but still not as long as a long-term tenant. At times, like high seasons, you’ll end up paying premium rates.

Many have tried to create specific platforms with accommodation for nomads, but no one has really taken off yet. The pandemic has pushed big established solutions like Airbnb to offer special deals for long-term stays. You can usually also negotiate with the place where you’re staying to get a better deal if you stay longer. And of course, pick a destination that suits your budget! In some countries in Latin America and Asia, you can live very comfortably for less than the average monthly rent back home.

Self-doubt And FOMO Are Real

When you choose to live an unconventional life, it’s common that self-doubt creeps in. Especially if those around you are on a more traditional path, that fits as perfectly with society’s expectations as peanut butter goes with banana. You, on the other hand, are out in the world trying to realize some big dream. On some days you might find yourself asking WTF I’m doing!?

Even if you know that you’re on the right track, results take time, and this can be frustrating.

lf you spend shorter times in different places, it’s also easy to feel as if you always should be doing something. Explore a new place, try a restaurant, work, or whatever. Even more so when you love doing those things!

It’s important to give yourself a break sometimes. You don’t need to do everything, everywhere, all the time. And that’s ok. You’ll always be surrounded by exciting opportunities, so learn how to choose wisely. Be grateful and excited by all the things you do instead of anxious about what you “might miss out on”. You can always re-prioritize, but you can’t do everything.

Not Let Financial Uncertainty Get The Best Of You

One of the biggest reasons why people don’t choose to start their own business or work as a freelancer is the uncertainty that comes with it. While your earning potential is unlimited when you’re an entrepreneur, success takes time. You won’t receive a fixed salary or benefits every month. Customers might suddenly end a contract or not kick off a project as planned, which can cause sudden reductions in income. You might also run into unexpected expenses.

While uncertainty and some financial stress are inevitable, it doesn’t have to be a constant worry. Find a calmer state by staying on top of your numbers, managing cash flow, identifying and following up on important KPIs like customer acquisition costs. Map out rooms for improvement and optimize your business over time.

If things haven’t worked out as you hoped for, take a solution-oriented approach instead of panicking. Right, this isn’t always as easy as it sounds. Accept the situation, be transparent, and see what steps you can take from where you’re right now to improve the situation.

>> 15 Effective Ways Entrepreneurs Can Better Cope With Financial Stress

Most People Won’t Understand You (But Think They Do)

Get used to that many won’t understand you, but still have all kinds of perceptions of you.

  • The most common is probably that you’re always on vacation, or even lazy. As you share experiences around the world, some might judge you. Clients could question your work quality if they see pictures from the beach, while new friends wonder why you’re not going out tonight again, and so on.
  • Parts of your family and friends won’t really get what you do, even if they are happy for you. My dad asked me just the other day what I work with now again (this is after 5+ years and counting).
  • Since you’re not part of the local community (yet) you will be seen as a foreigner, and often as a tourist. It’s nothing wrong with this, but you may miss the feeling of not being an outsider. Also, since you aren’t a typical tourist, you might not feel as drawn to the stereotype who visit the same places only to party and check off the main attractions, either. Even if you enjoy those things as well, you have other priorities too. You’re in this strange place in between.

Don’t take others' perceptions of you personally. Instead, focus on living your life in a way that makes you feel fulfilled. This can be hard, especially if you still have a lot of people from your “old life” in your network. Sometimes we just want to feel understood. Over time you’ll connect with other like-minded people who “get you”.

Choose clients, business partners, and friends who accept you, instead of judging you. In the end, what matters are the results, and you will have much more fun this way!

Your Suitcase Is Now Your Wardrobe

If you don’t have a fixed base, or even if you do and will be away for a long time, you have to carry all your belongings with you. I pack to be prepared for everything since I do many different activities in all kinds of places. From business events and hiking to beaches and nights out.

I prefer traveling light since carrying around too much can be tiring when you move all the time. The nomad lifestyle teaches you to become very conscious about what you purchase, which is a good practice! Mindful consumption is a great habit to embrace since it boosts your wellbeing as well as reduces our impact on the planet. I can still miss having more options, but in comparison with all the experiences I’ve had thanks to this lifestyle, that becomes insignificant.

>> Packing tips and answers to your most common questions about the nomad lifestyle

Establishing Genuine Relationships Even When You’re Always On The Move

Always being based in different places can make it challenging to maintain and develop new, meaningful relationships. You invest time and energy into getting to know people and before you know it, you or they will move on. It’s also time-consuming to stay in touch with family, friends, and those you meet, even if you want to!

When it comes to dating, it’s easy to find someone for a romance or an adventure, but trickier to develop something deeper. It takes time to get to know someone. And when you do, it can still, understandably, be hard for those you meet to accept your lifestyle if it’s different from theirs. There will probably be times when you wonder how things would have turned out if you were living in the same place. At the same time as you want to continue to realize your dream life.

It’s definitely possible to develop meaningful relations with this lifestyle though, and necessary to feel good long-term. It just requires some extra effort.

A Good Work Set-Up Isn’t Easy To Carry Around

You will likely, and especially in the beginning, spend a lot of time in front of the computer. While this isn’t very different from the average person who spends most of their waking hours staring at screens, it isn’t ideal. Moreover, it can sometimes be challenging to ensure a high-quality work environment. Things like a comfortable chair, a desk set at the proper height, a monitor, good lighting, and so on.

While your Airbnb or local coffee place might be charming, you can question how ergonomic their set-ups are. If you’re not careful, you might start feeling the physical strain on your body over time.

Prevent this by working from co-working spaces if that’s your thing, finding an apartment with a set-up for professionals, making sure to not sit down too much, or staying longer in places and get what you need. Take breaks to stretch and move, embrace stand-up meetings, and so on. Only your creativity sets the limit. Massage and other treatments to spoil yourself and put things back into place should not be underestimated, either! ;)

“Settling Down Things” Can Get Trickier

Such as having a pet or kids. You definitely can, you just need to add a few more things to your to-do list then. Like decide how to approach your kids’ education, and check if your cat is allowed to enter Brazil. It will naturally affect your travel style, too. You’d likely go for extra slow travel, which will allow you to get to know the place and the culture better! There are many examples of nomads traveling with both animals and kids. Personally, I think it’s great for kids to start traveling early, as nothing teaches you as much.

The cravings for novelty and adventures might also become addictive. While I wouldn’t say that I’m addicted to constant change, just as I’m not a coffee addict even if I love drinking it daily 👼, it can be more difficult to slow down at first when you’re used to a life filled with adventures and variation. This isn’t necessarily a bad thing but can make it challenging when it comes to relations, routines, choosing one (or several) place(s) to live, etc.

Career Development Won’t Happen By Itself

If you have ever worked for a well-established brand, you might be used to an organized career development structure. With mentorship, knowledge-sharing meet-ups, and a diverse professional network.

When you’re running your own business as a location independent entrepreneur, however, not much will happen if you don’t actively look into what areas you’d like to further develop. This goes for networking, mentors, and knowledge exchange in general. You have tremendous opportunities to learn more than ever before, you’ll just need to be very proactive! Make it happen, or it won’t.

The Nomad Lifestyle It’s About More Than You And Your Laptop At Dreamy Destinations

The nomad lifestyle is about so much more than exploring the world while working from your laptop. The lifestyle can be amazing, but it also has its challenges. It’s up to you to decide whether the pros outweigh the cons!

If you decide that you’d like to go for it, having a plan and some savings and/or cash flow before you get started will make things easier. Consider starting small first, by trying it out for a few months and seeing how you feel! You can always change your mind later.

As Mark Twain’s cliché quote so truly states; “You will be more disappointed by the things you didn’t do than by the ones you did”.

The choice is yours.

Originally published at on February 9, 2022.



Stuck in a boring routine? It doesn’t have to be that way. Learn how to design a flexible and location-independent lifestyle that allows you to be wherever you want, whenever you want while working with something you enjoy. How to think to get the most out of every day.

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