Digital Nomad Life Lessons from my Travel Destinations

Insights from My First Long-Term Travel Destinations

This article serves as a life lesson diary. In each base (where I stay over a month), my aim is to have learned something that will impact my future. The understandings have to be powerful, not a simple Aha moment, but a game changer in a specific area of life that can help me live a happier life. Sometimes it takes years to understand what those important lessons were, but from a distance of time, everything is clearer. When I reach a point everything is perfect, and life is optimized, I will quit this lifestyle and start some new chaos I can learn from. It is also my way of tracking the locations I have visited since 2010. A quick warning I always repeat is the following: Those are my understandings and lessons. Implementing some of those can result in making you miserable or not fit your lifestyle. Take the time to figure out your understandings, spot them as they happen, document them and play around with them. Listening to yourself and optimizing is key, and can only be done if you are constantly open to changes with a mentality of questioning the status quo. If you are interested in a more organized version of my current rules without any reference to the experiences or locations, please refer to my digital nomad case study article. It is not updated, and never will be, but provides a snapshot of what my set of rules used to be in the past.

Part 1

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Part 2

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Highlights from “Insights from My First Long-Term Travel Destinations”

Bases 0: Israel (August 2010 to January 2011+ Many visits in between)

Although Israel is my home country, it was also the first place where I lived as a nomad. Here, I resigned from my 9-5 accounting job, started my own business, got my first freelancing gig on Odesk (now, Upwork) and made the leap into a nomadic lifestyle. Since a nomadic life has a learning curve, you learn a lot in your first destinations, so my initial time in Israel (plus going back to it frequently) produced many valuable lessons that are relevant to this day.

Build it for a few months before you are starting 

This understanding is especially important if you are building a business, but also relevant for setting up nomadic infrastructure for all of us. The idea is simple, stay a few months in yourbase before you start moving around. Setting up a bank account, bureaucracy with tax authorities, other infrastructure, those all take time. Be patient, and build it first, once you start moving, it gets harder to deal with basic things from far away and it won’t let you to truly enjoy the path if you take off too early. 

Don’t be a nomad in your home

Especially when you start, it can get confusing. You are letting go of your ego, making a radical definitions change. The beauty on the road is not knowing anyone and experimenting the first nomadic steps without your close connections and society judging you. Pro tip: Nobody judges tourists and travelers. Trying to declare your nomadiscm at home, and living it where home is will create unnecessary frictions and worries for your circle. Living as a nomad outside of your natural environment, at least in the beginning, will allow you to experiment with this lifestyle and achieve equilibrium without the pressure of what society (and especially your ego) are expecting from you. Be lost in a place where you are expected to be lost at.

Have a sedentary ally 

This is especially if you are starting a business or a startup. Having a business partner who is sedentary gives you the backup to dive into surprises while traveling, while having the backup of a partner who can take care of things while you are gone. Regardless of what you do, build a structure of support at home that will help you with mail, communication with relevant organizations (banks, social security etc.).

Don’t go Ultra Nomadic

I didn’t know what would the nomadic life look like when I started. My initial idea was revolutionary (and stupid in retrospective). Never spend a night in the same place. After a month of doing that while trying to build a business, and a little short of losing my sanity, I have started to understand that the ultra nomadic model is a disaster. This period was valuable showing me how theoretical ideas that seem logical (e.g. communism) are not practical. It also created instability and loneliness where I actually missed my office social life. The seeds of understanding the importance of slow travel and coworking were sown through this experiment.

Have one place declared as home and constantly go back to

The nomadic lifestyle is unstable. One way to anchor and stabilize it would be to set a home base. Many of the most grounded nomads I have spoken with (e.g. Derek “wandering” Earl and Chris “HoboCEO” Kirkland) mention their home base as a positive force. In my case, I chose Israel as my official home-base, or the place I am from. The considerations of where your home base should be are dependent on what is important for you, and in my case, have to do with where my family is from, and beliefs on history or safety. For others, it’s a place they love the most, or do business. The bottom line is as following, living a nomadic life without any place to consider a base, or home, was not good for my psychology. Knowing that the nomadic life breaks with visits to this special place of yours, will allow you to take short vacations from this self definition, which is not bad at all. At home, I am normal.

Build a set of activities and enjoying routines for home

Optimizing your home base is more important than optimizing your routines in other bases. The reason is simple, the benefits multiply every time you go back. Your home base has another special characteristic, you will easily find yourself stuck there for much more time than planned for family and business reasons. Conclusion: Make it fun! I have made it a special priority to enjoy my time at home by assembling a few powerful routines and understandings. The first of this was the importance of spending time with my family. Since I don’t see my family much, I make a habit into seeing as much as I can of my family when I am at home, focused on quality happy time with them. Other than that, I have a weekly camping week in Eilat I try to do every time I go back home. I have also found a source of joy and a powerful ally in the sea, which is relatively close to my home, and I try to visit on a daily basis. Enjoy home.

Bonus: Disconnection weeks

This understanding could have came everywhere, but maybe it’s no coincidence it arrived in one of my home visits. Week of disconnection. What is the nomadic life all about if not freedom? How free you are if you keep on moving, but can’t disconnect from your work? Forcing yourself into those weeks will also create a more healthy work environment where you are not the only one taking out fires. In Israel, I have started a tradition of weeks of disconnection where I don’t check emails or do any work related stuff every quarter. Those quickly became the highlight of each quarter. Retire a little bit right now, because you might only be successful when it’s too late.

Another bonus: Daily 30 minutes exercise routine

In my first week of disconnection, as I have seen an old mysterious man in one of the nearby tents in the red sea doing Tai Chi exercises with a sword and weird outfit. I did what I always do. Looked at him with suspicion at the beginning, swore to myself I will not become like him as I get older, and then had an insight of a 30 minutes exercise routine I follow to this day. The idea is simple, as you are traveling between locations, you are never guaranteed to find a gym, swimming pool, bicycle, or have good weather. 30 minutes of daily random stretching routine a day with a timer can be done anywhere and keeps you happy and healthy. Try it.

India (January 2011 to April 2011)

Pick a destination that fits your current stage of life

India was perfect as a starting point. When I started, I practically had no clients and my business was just building slowly. Therefore, the lack of good internet, the possibility to dive into spirituality, enjoy the extreme low cost and the constant magical surprises India gifts on a daily basis made it the perfect location. Today, with my life circumstances of focus on business, clients and need of stability as I do it, India would be a very a very frustrating location to go to. Time is not a renewable resource, so picking the right place for you at each phase of life is recommended. Picking your travel destination wisely makes everything easier and happier once you get there. In India, I tested for the first time work and travel combined, and it was also the last time where travel was more important than work. I miss India not only because of India, but also because it was the last place I was truly traveling as first priority, before work became the new center.

Your travel destinations can help you improve your habits and ethics

I always knew eating meat was wrong. But it always seemed to me that I got so used to it and there is no option to stop. In India, I just stopped. Considering cows are a sacred in India, meat was off my plate for the months I have spent there. After seeing a a few trucks with chickens cramped with the worst sanitation conditions there could be, I understood that I am seriously risking my health by eating chicken. Unintentionally, without any conscious decision, I stopped eating beef and chicken. And it was all ok, I was just as healthy as before, and didn’t even miss it after a few weeks. After leaving India, I greatly decreased the quantities of meat and chicken I consume, and stopped eating it all together about 2 years after. The bottom line is that habits are much stronger than ethics. By not trying to test my discipline on my own good will, India just forced me to give up animal products. I am still eating fish and eggs (my basic rule is “avoid it, if it screams when it dies”), but happy that I have taken a first step to stop taking part in unethical behavior. India taught me to do that, and I think that if you want to work on new habits or let go of bad habits, picking a base that accommodates this behavior can be critical.

Arequipa, Peru (June 2011- November 2011)

The impact stability and staying longer has on your business

In Israel I understood that moving every day as an ultra nomad can make life impossible. In India, I stayed up to a few months in places I really liked. Arequipa was special, as it is the only city until now since 2010 where I stayed a full 6 months period. The main positive impact of that was on my business activity. I practically worked every day from 9AM to 9PM, and the impact it had on my businesses was immense. My online language school was finally making sales, and my freelancing career transitioned from working for $3 hourly to making business plans of $2,000 each with a cool partner from Pakistan. Consistency, focus and hard work have a powerful impact. Add to that the time saved when you stay in one place, and you can generate massive wins. Conclusion: If you are in a critical period with your business, or want to make the first few substantial wins, staying longer in a place makes a lot of sense. Warning: In business, it always seems like the current period is critical, so it’s an art for itself not to get confused on this point.

The importance of weekends

As I was drifting in India, I never knew which day of the week it was. I was proud of it. I took days off, worked on Saturdays, and was fine. In Arequipa, I noticed that starting Friday noon, working was a drag, depressing and stressing me. And working on Saturdays was even worse, total disconnection. Fridays and Saturdays were always off for me in Israel, I got used to the concept of no work on the Jewish weekend (Friday and Saturday), that when I tried to ignore it, I felt a negative impact. Since Peru, I stopped working on Friday afternoon and just go somewhere for the weekend. You can read more about my weekend routines here, and I am super grateful for Arequipa for teaching me about how important weekends are. 

Buenos Aires, Argentina (November 2011- January 2012)

It’s not the place you love and miss, but your situation in that place

In 2003 I first arrived to Buenos Aires as a backpacker and fell in love with the city. Everything fell into place, an amazing place after trekking for months, relationship, friends, low cost, everything. I decided I want to go back and live there one day. At 2011, I came back older, and in need of working on my projects for a minimum of 8 hours a day to keep the Arequipa momentum. It was no longer fun. Stress of work, all my trekking friends gone, girlfriends married, prices hiked. The city mostly stayed the same, but I have learnt that the real magic came from somewhere else. It was my life in the city that I loved, a unique set of conditions that can not be replicated with time. It was the mindset I was at, my friends, and things that I haven’t seen before that appealed to me. The big lesson? A destination you loved in the past might not be so enjoyable in the future. The bonus? Places you absolutely couldn’t deal with and disliked might be your favorite the next time you visit.  

Coworking is a life changing gift

At one point in Buenos Aires, as I was working daily from a small chair at home, I felt mentally depleted. When I told my friend Laura about how much I dislike to work from home and coffee shops, she told me about the concept of Coworking. It was astonishing for me that those places exist. It was also astonishing for me that I have to pay to stay in an office, since I was used to getting paid for being in those places. To cut a long story short, the advantages of coworking are amazing, and I honestly don’t think I could go on with the nomadic lifestyle for so long without the social and work benefits those spaces provide in each place I stay in. Praise the nomadic god (who ever it is) that Coworking exists.

Couchsurfing is another life changing gift

Here, I also started using Couchsurfing as a tool to meet people as I travel. The amount of friends and experiences I have had thanks to this platform is mind blowing. The people there are super awesome, and there is truly a couchsurfing spirit that makes the best of the best join. If you join, please keep this spirit, I can’t recommend this platform enough for hosting, surfing and meeting people for random coffees and hangouts.

Asuncion, Paraguay- Hidden locations are where the magic is (January 2012- March 2012)

I love underdogs

Bring me to your Asuncions, Burmas and Minsks. Is it off the beaten track? I love it. Is it an underdog without tourist attraction? I feel at home there. Paraguay is probably the least touristic country in South America which is the reason I love it so much. Good people, authenticity, real human interactions, campesino (farmer) lifestyle. I learnt in Paraguay that I am more happy in locations like Asuncion than in highlight locations like Rio, London or Prague. My main touristic attraction while staying in Asuncion was hunting for arroyos, small creeks that have water flowing outside of the city, and swim or put my legs in them. They were charming, exciting to find, surrounded by nature and had no mention on lonely planet or tripadvisor. Magic is everywhere.

Places are changing fast

Remember Buenos Aires? It’s your situation in the place that changes, not necessarily the location itself. In Paraguay, the location itself changed drastically. In 2003, I found home in a small village call San Ignacio de Guazú. It was small, magical, non touristy. I planned to stay one night, and ended up staying more than a week, discovering it day by day. In 2012, less than ten years after visiting it for the first time, I came back. In my first day there, I had to look at the map to make sure it was my beloved village. Many more cars, more people, more shops. The pace of development is incredible in some places. Conclusion: Those amazing hidden places you find now will change, and not always for the best. Take advantage of enjoying the magic if you found it, since all magic is temporary. One more interesting insight. Since news about magic become a consensus relatively slow, when this consensus is formed, the place will probably not be as good as it used to be. Try finding those locations before they become mainstream. 

The magic of a good accommodation

Asuncion was a first location were I found a magical hostel. Sorry for overusing the word magic by the way, but magic is what I seek. As time passes, I understand that happiness for me is correlated to 3 components. A great travel destination with many social and business opportunities and nature. A great office, where I spend most of my days. And a great home. It is not easy to find a magical home, but for me it means the following. After the obvious basic infrastructure such as the ability to get a good night sleep and safety, what really makes the difference at home is one word, Community. A place where you can make friends, or have interactions that make you feel at home. It usually starts with an owner that doesn’t take interest in making money, but honestly cares about interactions and getting to know their guests. In Asuncion, I found this place, in the form of an hostel that is now unfortunately closed. Amazing host, and a tribe of travelers that formed there, with some of whom I am still in touch to this day. A home, a real home, and a family. Those places are so hard to find, but I keep searching.

Barcelona, Spain (June 2012- August 2012)

An economic crisis can be a gift

The places you can’t afford can suddenly become affordable. The best way to achieve that is to earn more and be able to afford them.  However, sometimes it will happen by chance. I first spent a few days in Madrid in 2003. I felt like Spain is one of the most successful places I have ever seen. The economy was bustling and prices were high. I knew that I wouldn’t be able to financially afford traveling there or anywhere in west Europe in the first years of my nomadic life. But then again, the economic crisis of 2008 has made some countries much more affordable. The most notable examples are Spain and Portugal which offered amazing value at 2012, which is no longer the case now. You have to hurry up and take advantage of new cost arbitrage opportunities before they disappear, and be the first one to encourage countries in crisis by spending your money there so they can bounce back. Usually the two things you should look for when identifying those opportunities are dramatic currency fluctuations and depreciation of a local currency, or an economic crisis which results in decreased prices.

The best accommodation can be far from the city center

As tourists, we always try to find accommodation in the city center. It makes sense if you stay in a place for a few days, but if you stay for an extended period, it doesn’t. Centrist locations offer less authentic experiences, while also being more expensive. In Barcelona, I found an awesome hostel in the mountains, far away from the city, but still well connected with public transport. Usually if you pick a place far from the city center, towards the outskirts, or even out of the city, you will also receive opportunities to see much more nature, or experience rural life within a short distance of the city center. Avoid the center.

Find a hobby you can do anywhere

Each travel location can offer you an opportunity to engage in a new activity, or learn a new skill. In Barcelona, I took advantage of the swimming pool they had in the hostel where I stayed, to start with the habit of swimming wherever I go to. This has become a life changing habit which I enjoy a lot, and only started because of an opportunity that arrived naturally. Since then, I always try to find that one special swimming pool wherever I go. 

The bigger and more touristic the city is, the less I will like it

I didn’t enjoy Barcelona that much. This seems a little crazy, since everyone likes Barcelona, and I was even afraid to share this insight with my local friends. Now I understand that it wasn’t really Barcelona to blame. Time after time, I find that I don’t find my place in the “Mega Cities”. Those are the cities that have way over 1 Million inhabitants, and are usually a touristic destination. Barcelona, London, Berlin, Prague, Athens. Not for me. This is to remind you that this list is personal and can’t be applicable to many digital nomads who thrive in those successful cities. The key is understanding what you like, and pursue it, and it took me a long time and many months in sub-optimal locations until I figured it out.  

Some things are a must regardless of cost 

Remember me discovering how important coworking was for me in Buenos Aires? Well, since Barcelona was much more expensive, I decided to skip it and work in my hostel all day long. It resulted in low productivity and happiness decrease. After that experience, I just decided that I am doing coworking regardless of where I am and how much it costs.

Some problems can fix themselves on the road

After going back to Israel from Buenos Aires, I delayed going to Spain for a month in an effort to take care of an injury I had in Argentina. After one month of physiotherapy in Israel which only made my situation worse, I decided to go to Spain with severe pain and hope for the best. In Barcelona, I accidentally found a Groupon offer for sessions of psychotherapy which solved the problem completely in a few sessions. Sometimes, traveling can help you find new solutions to old problems.

Tackling fears is better where you are not home (Public Speaking)

I always thought public speaking was not for me. However, since starting the nomadic life, I also understood the business and social potential that public speaking can have, since now I had an interesting story to share. In Barcelona I started to actively pursue public speaking opportunities, and after giving two talks in the wonderful EADA University and a local startup meetup group, I discovered my love for this activity, and that I wasn’t too bad in that also. Since then I have been invited to speak in dozens of opportunities, including OECD conventions, TedX events and many other interesting venues. Conclusion? In home we have a lot to lose (or at least, that’s the story we tell ourselves). Take advantage of not being home to try the things that scared you, but have no real implications, other than making you a better person.

Granada, Spain (August 2012- September 2012)

Community homes and great AirBnbs are the best

I didn’t enjoy Granada that much when I arrived to a crowded hostel in the city center. But then, following the lessons I have learned with my remote hostel in Barcelona, I tried to look for a place outside of the city. This was the first time I used AirBNB, and found a great host in a small village half an hour bus ride from Granada. I later moved to a hostel in the same village which had a great community, while being surrounded with amazing nature. The lesson was re-enforced, if you can go out of the city to a place that is well connected to it so you can travel daily, that’s the optimal solution. The only disadvantage to staying in those places is the limited transportation options to get back when it gets late. You will feel just like Cinderella, trying to catch the last bus/train cutting short your social shenanigans, but that’s a small price to pay.

Picking a destination where you know the local language is a giant bonus

Barcelona was so international, that I used more English than Spanish. However, Granada was more Spanish in nature, since it’s less touristic and located in Andalusia. Speaking Spanish fluently was a great bonus while traveling, and I am still drawn to Spanish speaking countries for that reason. It simply upgrades your trip when you can speak the local language and connect not only with the “cosmopolitan” people, but also with everyone else, in villages, and from different segments of the population.

Being forced to leave because of visa limits is not always a bad thing

I really enjoyed Spain and would probably stay longer, but you can only stay in Schengen countries up to 3 months in each period of 6 months as a tourist. Countries legal stay period limitation is something each traveler is thinking about in the back of their heads, as we travel. In some cases, this limitation is bad, since it pushes you away from places you like. However, in other cases, it pushes you away from comfort and the familiar, to new destination. It keeps you on the road, moving, constantly thinking of your next destination.

London, England (September-October 2012)

Your dreams locations can also disappoint you

England attracted my attention since I was a child. I always connected to British humor, TV, and felt like the culture and lifestyle is exactly what I am after. Before arriving to London, I was actually worried about the continuance of my nomadic life, once I arrive to my “dream location”. Alas, London turned out to be very different to what I imagined. It’s very international fast, big and money-oriented. Not at all the image I had of it. I have probably made the mistake of staying in London instead of going to other British cities, but in any case, England was a disappointment and I left it much earlier than planned. Conclusion: You can only know how you feel about a place when you arrive there.

Pick a location that fits your budget

My disappointment of London was also probably due to it being an expensive place. I had a very tight budget and my quality of life suffered from trying to adjust my budget to the new cost of life. I switched my airbnb room in Spain with extensive use of dorm rooms in hostels, as I spent a month in a 16-bed dormitory, and eating at fast food chicken joints to save money. If you are still on a stage where your finances are limited, it doesn’t make sense as a digital nomad to pick a location that has high cost, because you then flip the cost arbitrage (working for clients in rich countries and living in low cost locations) against you.

Your spending stays the same, it’s your quality of life that changes

The realization that my spending budget doesn’t change much even in places which are 3 times more expensive than others, was a powerful one. In London, I noticed I would spend around the same amount of money I would spend in a low cost city. But while in London Airbnb rooms or apartments would become shared dorms, Sushi daily dinner will become trying to shop for discounts in Supermarkets, and taxis would switch in buses or walking, since buses were so expensive. There is an internal psychological limit that we put on our expenses, and you should note that if that limit is too low, your quality of life will greatly decrease. On the flip side, you should also prepare that your style of living will become almost luxurious in low cost locations like Ukraine and Chiang Mai.

Take advantage of being in Mega City

There are a few cities in the world where so much economic activity takes place. London is one of them. Although you can’t work in the country where you are staying as a digital nomad, you can still make incredible contacts with high level people, at the top of their game. You can schedule meetings, go to meet ups and make great connections that will become a valuable asset in the future. If you’re the kind of person who has big ideas and the ability to network, being aware of the great opportunity those cities offer and being proactive to pursue them makes a lot of sense.

Destination 8: Zagreb, Croatia (3 months)

  • Surprising connection. Zagreb has a reputation for being one of the most boring places in Europe, but for me it was amazingly interesting. It was my first encounter with a place that’s influenced by communism and the cold war. Maybe it was the familiarity I felt from Israel, but something there created very deep connection. I was just happy to be there.
  • Community. Most of the people in the hostel where I stayed, were on a long-term basis, and mostly locals as well. I connected very fast with the hostel guests, the hostel owner and even the owner of the coffee shop downstairs became a very good friend. I learned that forming a community is absolutely crucial for your happiness. It makes you feel that you’re a part of something, but unfortunately it’s not easy to find.
  • First European winter. During the winter of 2012, the temperatures were extremely low in Zagreb and it was snowing as well. It was my first time in those conditions. That winter was very harsh, but very beautiful at the same time, and I haven’t decided yet if I want to spend another winter in those conditions.
  • Home is always there. As you know, I’m originally from Israel, which has a long and complicated history. During my nomadic lifestyle I expected to lose a bit of my connection to my birthplace, but surprisingly, my ties became stronger. One of the things which shaped my re-connection was the antisemitism that I encountered, in high levels, in Croatia. It makes you realize how important it is to have a safe place to go back to, if necessary.

Destination 8: Belgrade, Serbia and Sarajevo, Bosnia (1 month)

  • Coworking, yet again. It’s so important. Without it, I simply cannot remain in a place for longer than a week, and that’s why I escaped Serbia and Bosnia early.
  • Geopolitics comes between people. After staying a long period of time in Croatia, Serbia and Bosnia, I didn’t see a big difference between the people of those countries. They all have the same mentality and even look a bit the same – but you can see how a big event can separate nations and change mindsets. How some are very pro EU (Croatia and Bosnia) and others feel betrayed (Serbia) and how the war wounds remain fresh for many years.
  • Reconnecting to my roots. When staying in Sarajevo (one of my favorite cities) I rediscovered how much I connect to Mediterranean mentality, which is common in Israel. I felt somewhat at home there, because my grandparents are from Iraq and Libya.

Destination 9: Athens, Greece (1 month)

  • It’s good to get away. Athens is a big, touristic city. And just like London, I discovered that kind of place is not for me. I do not feel at peace in a capital city. What I thinks helps when you stay in a big city, is finding a place to run away to on the weekend. Athens has a big port called Piraeus and every weekend I would take an hour boat ride from Piraeus to a peaceful island, Aegina.
  • Air B&B: Athens was the first place where I shared an apartment with someone, using Air B&B. Instead of jumping between locations in the city (from one hostel to another), renting gives you the energy to get your work done. I’ve been using that system ever since, and I really recommend it.

Destination 10: Thessaloniki, Greece (1 month and a half)

  • Read a book about the city. I had an instant, unexplained connection with this Mediterranean city. It’s close to the seaside and also has a lot of interesting history as well. When arriving, I received a book about the history of the city that gave me a lot of context. I could really understand the story behind Thessaloniki, as I walked along the streets. I think reading a book about the place can really upgrade your experience.
  • A good friend makes a good stay. I met a good friend in Thessaloniki, and that made all of the difference. A good friend that you trust and can spend time with, gives you a feeling of belonging to the city. It also opens a lot more possibilities – they can show you around, introduce you to their family and just improve your experience altogether. Those relationships are also something that will stay with you after you leave. It’s a great boost to your happiness, and offsets the disadvantages of the nomadic lifestyle.

Thanks for reading or listening!  I will post another podcast soon about my travels in more recent times.  Tell us about your own amazing (and not-so-amzing) travel destinations in the comments for this post.  And make sure to tell us what you learned along the way!

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