The first time I heard the concept of a “digital nomad” was back in 2016 when I was hosting a barbecue (or better say “un asado”) in my apartment in Nuñez, Buenos Aires, Argentina with friends and friends of my friends.

“Is it ok if he crashes your apartment for 1 night? He is a nomad. He’s part of this group of Digital Nomads in Buenos Aires and tomorrow they have an event close by.”

I didn’t know what to say. I’m usually very welcoming but all I could think was


“Should I let a stranger who happens to be a guy stay in my apartment? How comfortable do I feel with it as a woman who lives alone?” Plus
 “A nomad?” “What’s a digital nomad?”

Long story short, I said no to that request, and a year later without really knowing, I was the one quitting my job and life in Buenos Aires and becoming a digital nomad too.

October 2017. After less than a year of preparation, I bought a one-way ticket to Chicago, USA and quit my job in a multinational company to pursue my dream of traveling the world full-time with my partner, Marco (and build our dream online business)

Little did we know with it, the whole transformation our lives would have. Since then:

  • We traveled around 4 different continents and 20 different countries.
  • We tried different travel lifestyles: hitchhiking, backpacking, housesitting, vanlife.
  • When we started we sold everything and packed our lives in a backpack. Nowadays we own our little home on wheels aka “Amy Hiroki” and we have more money than when we started.
  • We thought we will travel full-time for maybe a year, here we are five years later and we don’t see an end yet.

We did all of it while building our own dream online business. 

So, if we consider digital nomads as people who travel freely while working remotely using technology and the internet then
 we are digital nomad entrepreneurs I guess.

These past years have been amazing, we never felt this alive and more in love with our lives BUT they have been also very challenging, especially on an emotional level.

We always need to pay a price, no matter which lifestyle we choose. The question is


Which price are you willing to pay?

Marco and I working in Mexico (2023)

Turning traveling into our lifestyle has been the best decision we ever made but we would have loved to know a few things ahead. So, along with this article, we gather not only some useful information we would have loved to have the moment we made the decision but also a few questions to ask yourself that hopefully will help you assess if you’re willing to pay the price it takes to live the  “digital nomad lifestyle”, “travel lifestyle” or a.k.a “laptop lifestyle” (or not)

In this article you will find:

  • 3 Pros & 3 Cons of being a digital nomad to asses if it’s for you (or Not)
  • The best Nomad Insurance for you as a digital nomad.
  • 4 questions to ask yourself if you decide the digital nomad lifestyle is for you.

I will go quickly through the 3 main pros and cons as there is plenty of information about it on the web. What I think will really make the difference for you is to ask yourself a few questions before embarking on this new lifestyle that will be unique to you because it’s yours and no pros and cons can figure it out for you.

3 Pros & 3 Cons of Being a Digital Nomad – How to know if it’s for me.

The Pros – most of it I’m sure you’re aware of most of these digital nomad benefits but
 here we go anyways!

  • Freedom. Freedom of location to travel and work wherever you want for as long as you want to (or until your VISA allows you to). You don’t have to worry about commuting or being tied to a specific location. No more begging for more days to go on vacation and explore the world. This freedom allows you to explore different parts of the world and experience different cultures.

    House sitting while working in Grenada (2021)
    “A friend with an available condo in a luxurious oceanfront residential community in the Dominican Republic for 1 month?” We are in (Yup! That actually happened back in 2020)
    “A 4-month house sitting in an oceanfront in the middle of the Caribbean in Grenda?” We are in (And, yup! This is also a real story from back in 2021)”
    “What’s the next destination on our bucket list we want to accomplish this year? (That’s a question we ask ourselves every year since 2018. That’s a life worth living, isn’t it?)

    Lower cost of living. We spend less than when we were renting an apartment. Depending on where you choose to live, being a digital nomad can be a cost-effective way to live. You can choose to live in countries where the cost of living is lower than your home country, and this can help you save money. What Marco used to spend in 1 month living in Chicago is equal to more than 5 months traveling. And, actually… Thanks to house sitting we not only spend less but we in fact save up to more than 20K USD on accommodation every year.

  • Personal Growth: Living and working in different parts of the world can help you grow as a person and learn how little you need to live. You will be exposed to different cultures, languages, and customs, which can broaden your perspective and make you more empathetic toward others. As a digital nomad, you move a lot and usually, you have everything you need in your suitcase: your passport and your laptop plus a good internet connection and you’re good to go! You learn to be not attached to material things. We carry with us the same amount of luggage in the past years.

Our life fits in 1 carry-on + 1 backpack. We never felt this free!

Marco and I hitchhiking the whole of Argentina (2019)

As much as we love this lifestyle, working from anywhere has its drawbacks.

Cons – The Things No One Had Told You

  • Detachment. You’ll go through detachment from groups where you previously used to belong and will have to create new ones along the way. For us, most of the time is just the 2 of us and we really need to make an effort to build that community where we feel we belong. So, You’ll need to make an effort to message fellow nomads in social media, join meet-up events and intentionally make new friends.

  • Grounding. Every time you move, you need to adjust to the new place and find your balance (again). This means finding where to do grocery, where to work, and where to exercise (+ adjust your stomach to the local food). The reason why we created Nomad Journal App, a daily journal app for dreamers, travelers, and nomads that helps you be motivated, mindful, and focused on what you really want.

  • Uncertainty and discomfort. Sometimes you won’t have the certainty of how or where to sleep. In the beginning, we were figuring out where to stay every week (yup! We were changing accommodation every 5 days) then we found house sitting and our period of time between houses or accommodation became longer, we usually house sit for a minimum of 1 month. This will involve research, planning ahead of time, considering the price, location, reviews, comfort to work, etc. Since we decided to build our own online business, we also don’t have a regular salary and we have full responsibility for our financial stability which means on the one side we can earn as much as we want to but also on the other hand, it means our income can fluctuate and sometimes (especially in the beginning) earn much less than what we used to earn in our 9-5 jobs.
    And last but not least, as in life itself emergencies and accidents could also happen (you’re in fact more exposed to it since you’re constantly moving) but having unforeseen medical emergencies when you’re in a foreign country can be even harder. That’s why having Travel Medical insurance is very important. We experienced 2 motorbike accidents, one in The Philippines and one in Thailand, nothing big but knowing we had our nomad insurance gave us lots of peace of mind. This leads me to our second point in this article.

The best Nomad Insurance for you as a digital nomad.

Since we started traveling full-time in 2018, we’ve tried 3 different travel medical insurances, (plus the ones before 2018 when we used to travel for vacation). I used to use “Universal Assistance” (btw, so bad! I hired their services twice because that was the only one I knew and it was enough for me to not hire their services again), and Marco used to use “World Nomads’” until after some research, in 2019 we decided to switch to SafetyWing, a travel medical insurance for nomads created by nomads (but it’s so flexible that you can even use it for your vacations)

We love SafetyWing so far! 💛 It’s affordable and flexible, you can pay monthly, and has very good customer service, and they make everything seem so simple! We decided to partner with them and become an affiliate because we believe that it’s really reliable and helpful for travelers and nomads. So if you decide to hire their services make sure to use this link, so you can also help us to get a small commission.

When you choose to travel the world, you are choosing to build a new lifestyle with more freedom and where you can combine your multiple passions and earn a living with them from anywhere in the world.

We chose to pay the price of living a life on our own terms with all its “pros and cons”. 

What price are you willing to pay to build and live your dream *digital nomad* lifestyle?

So, if after reading all the pros & cons about a digital nomad lifestyle, you’re ready also to pay the price for it and embark on a digital nomad lifestyle then


Here are 4 questions to ask yourself to help you start designing your best freedom *digital nomad* lifestyle:

  1. For what do I want to travel? What’s the purpose behind my decision? This question can change it all. It’s not the same if you want to travel to discover new passions and let yourself be surprised and go with the flow that if you want to travel to learn about feminism in South America while working remotely. This will mark the direction on how you’re going to map the unknown of this new lifestyle.
  2. What does it mean “freedom” to me? How much freedom do I expect in my work schedule? Often times we see nomads experiencing burnout because (yes, they’re traveling the world but…) they’re working in something that not only consumes most of their time but also doesn’t fulfill them. They left one “prison” and created a new one. This leads me to the next question

  3. How do I want to earn a living? What’s my dream job? Perhaps you want to do any seasonal jobs, save up money and go and travel but how long is it going to last? Having a deep understanding of what you want to create with your job/business will help you either find companies aligned with it or create a business that fulfills your purpose and make your digital nomad lifestyle more sustainable in the long term.
  4. How does “balance” look to me? What makes me feel balanced? This is key. You won’t have an office where to go from 9-5 that will dictate your routine, you’ll need to find and design your own structure while experiencing different time zones. Answering this simple yet powerful question will help you design a routine that helps you feel grounded and balanced, and productive with your work no matter where in the world you are. 

This dream has been more than places to be discovered or new experiences, it made us fall in love with our lives every single day. It made me shed a tear just to remember all the wonderful experiences we were able to have.

If you also have the same dream of traveling the world living the so desirable “digital nomad lifestyle”, if we could do it. You can do it too!! 

One decision, one leap of faith, can change it all.

What else would you like to know about having a digital nomad lifestyle? If you’re also a full-time traveler or nomad, what else would you add to this list? đŸ€Ș

Leave in the comments any questions you might have. We are always happy to answer and help!

Remember these 5 essentials tools for your travels:

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