Living the Dream as a Digital Nomad

I AM living the dream, here’s how

Yesterday, I read a very interesting article by Charlie Guo, a traveler and a digital nomad. The title of the article was I’m Not Living The Dream.

In my opinion, Charlie did an excellent job of outlining the problems that digital nomads face. People who live on the road and work while traveling face a unique set of challenges different from those that live relatively stationary lives. In the past, I’ve discussed the hard things about long term travel.

We tend to take the good with the bad. So, although we post beautiful things on Instagram, we still write about the horrible experiences that we’ve had. Like when Hertz treated us really badly, or when we stayed in a haunted AirBNB house, or even when we discovered a new type of spa treatment – Poo aromatherapy. We even have an entire section called Travel #FAIL! So this venue is definitely not about glorifying a travel lifestyle. We take lots of pride in telling it like it is!

The intro to Charlie Guo's article

The intro to Charlie Guo's article


Charlie starts his writeup by talking about how he feels tired of ‘perfection’ (a beautiful beach, a stunning sunset, a towering mountain.. mean nothing anymore) and then moves on to talk about loneliness, and even mentions what I call decision fatigue.

I enjoyed the article, even though I do not agree with it. I found it insightful because living on the road for four years, Zara and I have faced the same problems time and time again. We’ve felt all the same emotions that he mentions in his writeup. That brings me to why I do not agree with it.

We’ve learnt how to deal with those problems. There’s an endless glut of people writing about how solo travel is amazing and inspiring and will be the best experience of your life. Solo travel, like anything else, can go both ways. I’m not going to say much on that. Couples travel also has its own set of problems. I’m writing this post because I want to share with you the solutions that we have found to make our travels satisfying and meaningful and although they may not apply to you, they might give you some ideas on getting creative with your own situation!

Long term travel is no panacea for underlying issues that people might or might not be having. If you’re feeling lonely in your regular life, long term travel may or may not help. What living as a digital nomad gives you is the flexibility to structure your life, location, and even schedule (depending on your work) for maximum satisfaction. Like anything else, you can fail at finding this structure or you can succeed. We’re still working on it, but are we happier than when we lived in Dubai? HELL YEAH!

I feel incredibly lucky. I thank my stars everyday for having a wonderful, inspiring, supportive travel partner. Yes, traveling as a couple comes with its own set of challenges, and we also feel lonely a lot of times, but at least we have each other. A beautiful sunset is so much more beautiful when you share it with someone else – and no, that does not mean sharing it with your Instagram followers. I find that a life of travel helps me be more mindful and I tend to live far more in the moment than I used to before.

The view from our apartment building in Puerto Rico - where we are at right now

The view from our apartment building in Puerto Rico – where we are at right now


In his entire article Charlie does not mention money as being a problem. This is the biggest issue that most people who live a life of travel often face. I don’t mean to minimize any of the issues that Charlie has faced over the years, but I would love to suggest some of the solutions that we have found.

Amongst us, we’ve often talked about traveling with purpose. Traveling as a tourist without purpose can get old really fast. For us, our primary purpose will always be to share things with our readers. We love writing about our travels and sharing our experiences through photos, videos, etc. We also write about social issues and other things that we care about. I love sharing my visa experiences as an Indian traveler. The truth is that we enjoy our travels much more when we write about them and share our thoughts with you! However, we’ve often discussed personal development as part of our life on the road strategy. Along the way, we’ve learnt how to surf, learnt how to cook exotic dishes, more importantly, learnt how to EAT exotic dishes, and I personally have learnt quite a bit of Spanish. Si, es verdad!

Ordering lunch in Taipei, and being up for whatever may be served...

Ordering lunch in Taipei, and being up for whatever may be served…


We still want to do other things that a regular life would perhaps not afford us the opportunity to do. Learn Mandarin in Taiwan, learn how to make Sushi in Japan, learn to sail off the coast of Croatia, climb a volcano in Guatemala (this one’s coming up soon!), dance salsa till the sun comes up in Cali, Colombia, and more!

When it comes to professional development, I’ve met lots of entrepreneurs and even started working on new projects while on the road. I’ve written more about those challenges here. My work and the challenges I face have changed a lot since then but it’s still a good overview. Back in 2012-2013 there weren’t as many digital nomads as today, it wasn’t a ‘thing’ back then. Now, you have a wealth of information out there on being a professional on the road.

I started GapJumpers while being a digital nomad

I started GapJumpers while being a digital nomad


That brings me to loneliness. This is definitely a tougher subject to crack. We’ve found that taking part in activities helps us meet people. However, that only covers a superficial interaction which probably will not result in life long friends. We’ve met a few amazing people on our travels and become really good friends but this is not something that comes with a guarantee and your mileage may vary.


From Charlie Guo's "I’m Not Living The Dream" article

From Charlie Guo's "I’m Not Living The Dream" article


However, we’ve found that with a life of travel, we’ve been able to spend a lot more time with close friends who live in different parts of the world, than we would have otherwise. In the 21st century people move around a lot. A lot of our close friends live in different countries and we’ve made it a point to go to their cities, live close to them, and catch up – REALLY catch up. We spend a few weeks hanging out with our close friends and get a taste of their lives and if we can do this forever, that would be such a beautiful existence! Fingers crossed! We’ve spent time in New York, Paris, Berlin, Lisbon, Delhi, Kolkata, and even Santiago de Chile in the past few years to catch up with our close friends and at the same time make new friends!

With friends in the US, India, Thailand, Portugal, Chile and Spain

With friends in the US, India, Thailand, Portugal, Chile and Spain


If we lived in one place with regular jobs, it would’ve been impossible for us to spend quality time with our friends abroad. In my opinion, for most people who have normal lives and schedules, the time to spend quality time with your friends (and even make close friends) is your early 20s. After that, if you live in the same city, you’re in luck, otherwise you’ll see each other only a few times if you’re fortunate and put in the effort required. Our friends don’t have the kind of flexibility that we’ve chosen for ourselves, but we love to go and visit them and spend time with them at any time of the year that works.

So the truth is that yes, I spend weeks without many close friends around me but the months in the year that I can spend with my close friends around the world are truly precious and a type of privilege that not a lot of people in the modern world get to enjoy. For this, I am truly grateful.


With Family. Above in Portugal and below in India.

With Family. Above in Portugal and below in India.


Not only that, but it’s important to mention that both Zara and I spend way more time with our families in Portugal and India. When we lived in Dubai and had regular jobs we’d visit our parents for a few days a year. Now we have the flexibility to spend weeks or months with them! So we end up spending more time with our families than we did before too!


From Charlie Guo's text

From Charlie Guo's text


We’ve moved fairly fast through the past four years and we are now trying a different formula that lets us live in different places and avoid decision fatigue. Moving too fast causes a strain on the senses. You’re always in a new environment having to choose a place to eat, a place to stay, a mode of transportation, and much more. There’s a certain joy in walking into your neighbourhood coffee shop and immediately getting your ‘usual’. We want to experience that joy and luckily, we can move as fast or as slow as we like. This year, we are planning to travel slower, spend more time in each place and get to really feel the vibe and rhythm of life there before we move on.


From Charlie Guo's article

From Charlie Guo's article


On being numb to glorious sunsets and mountaintop views. Too much of anything can be boring. We’ve dealt with this by mixing it up all the time. Rather than spend all our time following the sun or living the tropical lifestyle, we like to experience different realities. Isn’t that what traveling is all about anyway? When you’re sick of beautiful tropical beaches and sunsets, experience a winter in New York and you’ll be running back to the tropics in no time – by the way, this is exactly how we did it. Spend some time in arid places like Dubai or Jordan and you’ll soon enjoy lush mountaintop views. Everything is awesome relative to something else. If you choose a life of travel, why choose just one type of thing?

After this, I think I'm ready for a tropical beach!

After this, I think I'm ready for a tropical beach!


The only real issue I took with Charlie’s article were his Expectation Vs. Reality pictures. I found them disingenuous and unrelated to the problems he mentions. Every touristic place has seasonal traffic. We found this even in the most touristic city in the world – Paris. With our flexible travel schedule, we like to visit places in the off or shoulder seasons. That way locals are less hassled, natural sites are more accessible and empty, and you have less obnoxious tourists all over the place. Oh and I almost forgot, everything’s around half the price! We’ve also often noticed that in most touristic cities, the moment you stray from the tourist trail, you will find yourself in a different world.

Smiley graffiti seen in Austin, Texas

Smiley graffiti seen in Austin, Texas


In the end, life as a digital nomad is not perfect. It has its own set of challenges and loneliness is probably the number one issue. This can be much worse if you’re in a place where you do not even speak the language. For me, as an Indian passport holder, visas can be quite a nightmare too! But every challenge has a possible solution and we’re not giving up on this life before trying at least a few different solutions to our problems. No, everything is not perfect, but it’s definitely worth it!

We’re young, we’re healthy, we’re able to work digitally on the road and sustain ourselves. If we don’t travel now, when are we going to do it? Not everyone has to choose this life, but it’s something new and exciting. Working online while living in different parts of the world has only really been possible since the almost global reach of highspeed internet became a thing. The internet, remote work, credit cards, globalisation, affordable international air travel, international health insurance, English becoming a global language, and many other factors have come together to make this reality possible for the first time in human history. Of course it’ll have some problems, but we feel privileged to be a part of this. If we manage to figure out even a tiny part of how to live internationally in the digital age, then we’ve somehow moved farther ahead than we were before. That’s a pretty huge thing!


Road-tripping in Puerto Rico

Road-tripping in Puerto Rico


For us, for now, the upsides are far bigger than the downsides. When that changes, we’ll settle down. And we’ll make sure to love every moment of that too! Until then, we’ll keep sharing stories from the road and we hope to continue enjoying all that this beautiful vast world has to offer.

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  • Anu Says

    I am very impressed with the depth of your feelings in doing what you are doing go chase all the rainbows not all people are all that lucky and courageous sunsets and beaches are part of all packages it is outside the package what you see and feel is what counts traveling does make you weary but the memories are worth it never give it up for anything

  • Love this post so much! I was nodding along to so many things. I think social media has a big role to play in how people perceive travel (and the freedom to be a digital nomad) – those perfect photos, those quotes that imply that every moment out there is going to be life changing. But then you find that the reality of being on the road is much like life – you are the only one who controls how you play the cards you’re dealt along the way.

  • Varsha Says

    Thank you for you insights. I find it inspirational and look forward to exploring the world as you and Zara have done. Love reading all your posts. Enjoy life to the fullest!

  • Horses for courses I say.

    Some people aren’t in love with the lifestyle, but then why do it? I’m happy to read that you guys are so happy with what you are doing, and balanced enough to realise that it’s not perfect, but then what is?

    Perhaps Mr Guo could reassess his expectations, or what it takes to make him happy. I don’t mean that as a criticism – everyone is different. That’s what makes the world what it is.

  • Anaise Says

    A good and touching read. My dream was always to travel, but when I did start traveling alone, I found that I don’t like not having someone to share it with. You guys are lucky to have each other. Even though I will probably not go traveling anytime soon yiu guys did inspire me to go and do something new.

  • Love your article and being honest that being a digital nomad isn’t always great.

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