Written by Kieran Proctor

Two Years As A Digital Nomad – Where I’ve Been And What I’ve Learnt

This is my first two years as a digital nomad. It’s more of a diary entry and it’s intended to ...

This is my first two years as a digital nomad. It’s more of a diary entry and it’s intended to show you, my readers, that there’s a big wide world out there to explore. And that you needn’t be chained to a desk working a traditional 9-5 job.

The notion that you can only work in a specific office at certain times of the day is old fashioned. We’re in a digital age and the internet has made the world of work far more flexible.

If you want to be a ‘digital nomad’ like me, you just need to think outside the box. And the first step is realizing that the things chaining you to your job or city are of your own making. They’re a product of your own choices to date. You can consciously make different choices.

Anyway, here is my first two years as a digital nomad living and working abroad.

Digital Nomad Rule 1 – Always use a VPN!

My First Two Years As A Digital Nomad

Leaving Australia in early 2021 bound for Europe with a single bag and no plan, I was determined not to be cooped up inside again. My days of office work and rolling lockdowns were over.

I knew I was going to catch-up with my Peruvian friend and tattooist Jimmy in Bonn. But I had no travel plans beyond.

I was just going to go out into the big wide world and get my life back onto the track I’d envisioned for myself prior to university. Somehow on entering into university my academic ambitions grew beyond all measure. And then adult life took hold.

I woke up one day living with my long term partner, engaged. I was working ridiculous hours as a government contractor for the Therapeutic Goods Administration in Australia.

And I had previously made my way through the Department of Home Affairs (Home Office or Homeland Security for my foreign readers). I’d become a sworn Border Force officer and I had been cited for excellence.

They had given me shiny badges and gold stars on my shoulders for slaving away at a job I hated.

Kieran ABF Awards
Me receiving a citation for ‘excellence’ from the ABF Commissioner

During 2020 I’d watched as the people I’d looked up to in the departments I’d worked for kicked one of my friends out of Australia. While continuing to pursue a near decade long vendetta against my then partner.

One day at the start of early 2020 I came to work as things were heating up globally, to be told ‘in light of current circumstances we’ll need you to do more hours’.  By the schmuck who’d just started and never did any overtime.

I’d already been working over 50 hours a week. Despite only being paid for 38.  Stuff this, I thought.

My instant reaction was to respond, ‘I’m a contractor and I don’t need to give you notice. So as of the end of today, I quit. Find someone else.’

I then worked for myself for the rest of 2020. Learning about websites and online trading. All while dreaming of once again traveling. Like I had in my younger days.

Being cooped up inside with my partner day in and day out was also getting beyond tolerable. I’m an independent person and I like my alone time. Which I wasn’t getting in our 100m2 apartment.

So when I boarded a plane in early 2021, with a one way ticket to Germany and no plans, I knew I wasn’t going back.

Heck, Home Affairs even made me sign an affidavit stating I wouldn’t return to Australia until quarantine had ended. So be it, I thought.

If I can get 8 university degrees while working beyond full time hours and do it with a GPA higher than most people can get in the best of circumstances, I can make a global travel life work for me.

It was time to sink or swim. To roll the dice and risk it all. So on that plane to Germany I was going. Nothing was going to stop me. I signed that affidavit and boarded the plane. Exit stage left.

Leaving Australia 2021
I escaped Australia in 2021

Where have I Traveled as a Digital Nomad in The Last 2 Years?

Arriving in Germany, I had no idea of the adventure that lay ahead. I caught up with Jimmy after 7 years stuck in offices and at university without holidays. And we immediately took up where we left off. At the pub.

We went straight out for a few pints of Germany’s best beer, Kolsch.

Definitely not Germany's best beer
Definitely not Germany’s best beer. Try pronouncing this after you’ve had a few.

And in our drunken stupor we designed my unfinished tattoo sleeve on my right arm. A full negative space blackout tattoo sleeve for my grandmother I’d lost years earlier.

Still hungover, that very next day we were into the tattoo studio for a full day tattoo session. And several more tattoo sessions would follow in the coming weeks.

Between tattoo sessions we’d travel across Europe and catch up with long unseen friends. Friends I’d made in Peru years earlier. Before adult life had taken us all hostage.

I’d take Jimmy to his first (and second) metal bars in Switzerland while catching up with Gio. And Jimmy would take me on a road trip through Europe and we’d visit Hungary and the countries in between.

Balatonfüred⁩ Annual Wine Festival
Annual wine festival in Balatonfüred Hungary

We spent a couple of weeks at Lake Balaton before hitting Budapest. Boy is Budapest wild. One of my favorite cities.

Because Jimmy had to work (and keep his girlfriend happy) I’d eventually go and spend time in Frankfurt, Berlin, Hamburg and slowly make my way all the way up to Copenhagen.

Where I’d catch-up with a former university friend who was then working in the Danish public service. And I’d go on yet more benders.

I love Copenhagen. But its too damn cold for me. Copenhagen had me dreaming of warmer climates. So I went back to Berlin.

Kieran in Copenhagen Denmark
Kieran in Copenhagen Denmark

In Berlin I bought a few blank visas from a strange man who offered to sell me visas for a whole host of countries. All in cash under the table. But I only wanted a visa for Cuba.

In Cuba, I had a friend I’d studied International Affairs with at the ANU in Canberra. And Cuba was looking a lot warmer than Europe by that point.

With that visa I bid Jimmy farewell during another all night drinking session and over far too many pints. And I hoped a train to Frankfurt where I thought I could get a flight to Cuba.

Buying the first available ticket I hopped a plane to Havana in mid 2021. And landed straight into Cuban Hotel Quarantine. F**k.

After 2 weeks of locking me in a hotel room, feeding me something vaguely resembling food, shaking me down for cash everyday and randomly appearing at odd hours to shove a stick so far up my nose it tickled my brain, the Cubans finally let me out into the big wide world of their tiny little island.

Escaping hotel quarantine in Cuba 2021
Finally allowed out of hotel quarantine in Cuba

My first day seeing sunshine in a couple of weeks, without hesitation I booked the first Airbnb I could find. And of course, I went out drinking.

That night I wandered out onto my stoop to get wifi and noticed all the police had retreated from my area at about 10pm. Then the knives came out.

Still unable to freely travel into and out of Cuba the tourists had all left. And the average Cuban relies on tourists to make ends meet.

As you’d imagine by mid 2021, having been without tourists for 18 months things were starting to boil over among the less affluent populations in Cuba.

So when I stepped out of my front door to get wifi and noticed all the police had taken off, I learnt that a running gang battle involving large knives, broken bottles and bricks had erupted. Right on my door step. Fantastic.

As a large knife whizzed past my face I resolved myself to finding a better Airbnb in the morning. And retreated back into my casa.

It was the following day that I moved into an apartment in the more upscale neighborhood of Vedado. And it would be the casa owned by the woman I’d eventually go back to Cuba to see.

You’d know her as Che Guevara’s granddaughter. I’d come to know her as Fanny, my gorgeous beagle loving Airbnb hostess. Who was both the most frustrating woman alive and yet so gorgeous.

Airbnb hostess with the most-ess

Fanny is just one of a long line of Cubans I made the mistake of dating. Which is why I say don’t date Cubans.

After spending months in Cuba, dating and then being rejected by Fanny, only for her to then date me once again before rejecting me anew in a never ending cycle, I decided it was time to bail on Cuba.

Plus by that stage I’d been roofied by a foreign diplomat in Varadero, made new friends and lost other and I was just utterly sick of ghetto life in Cuba.

So it was once again exit stage left.

I booked the first available flight to Buenos Aires Argentina. My favorite city in South America and where I’d spent quite a bit of time in my youth.

I booked the first available flight and was on my way three days later. Arriving in Buenos Aires and being thrust back into the civilized world was a shock, after about 4 months in closed off Cuba.

Even after Cuba reopened in November 2021 there was still the further threat of more protests and just the constant bulls**t that Cuba throws up each and every day.

‘Oye’ Cuba. Get your s**t together.

Arriving in BA was like walking off a plane into another world. A world I would be loathed to leave for the next year.

Well, that is except for the occasional trip on the Buquebus to renew my Argentine tourist visa and explore neighboring Uruguay.

If you’ve never had a ‘Chivito al Plato’ in Uruguay it can only described as the turducken of steak. And it’s glorious. It’s another reason to visit Uruguay.

Uruguay Chivito
Chivito al Plato

But back to Buenos Aires. It’s a modern metropolis of over 15.5 million people. With all of the modern amenities.

Every barrio in BA is different and there’s always something new to discover. It’s a digital nomads Graceland. You can work and explore. Balancing life and work in BA. It’s such an amazing city. And it was even more amazing than normal, during FIFA.

One thing that will stick with me for life, was the sound when the final whistle blew and Argentina had emerged victorious. All at once every single inhabitant of Buenos Aires shouted. The entire city erupted into a roar.

The partying didn’t stop for weeks after Argentina secured the World Cup trophy. I’ve never seen the city so alive. And I probably never will again.

A few weeks later it was back onto a plane. And back to Cuba from Uruguay.

Starting a Youtube Channel in Cuba

Returning to Cuba In 2023

A couple of Cuban friends had been pestering me to help them. And they wanted to start a YouTube channel. So, okay. Back I went to Cuba.

I landed in Cuba the day before Xmas 2022. And spent the next 3 months in Havana and it’s surrounds.

Yet the boys being Cuban had just wanted it all to work out with YouTube without any form of effort. Cubans man, they’re all just lazy.

Communism has ruined Cuba. None of them have any form of work ethic. They all want the luxury goods and money to come the same way their chicken and rice does. Free and without any form of work.

You should think of Cuba like a country sized amusement park or a real life ‘West World’.

So it was back onto a plane for me. I wasn’t going to waste any more time and money in Cuba. I’ve seen more of Cuba than most Cubans. And I don’t need to see more.

I’ll go back with a fresh mindset and see it once more after the communists all die off of old age, or are booted out by military. Once Cuba gets its s**t together and becomes a functional country and not a country sized amusement park, then I’ll consider going back.

Booking a flight out of Cuba was a drama in itself. Thanks to the American Government and a useless airline booking website. Half the airlines had redirected through the US but the embassy hasn’t caught up with the policy changes and won’t likely catch up for a few years.

I needed a ‘transit visa’ but couldn’t get one in Cuba to transit the USA. Because the US embassy in Cuba still haven’t as yet hired staff to process transit visas.

So I did the most logical thing, I took a flight from OMIO to Bogota Colombia. And Bogota is where I am now. Winding out my first two years abroad.

Bogotá or more precisely ladies in Bogota are why I say do date Venezuelans. But more on that when I write the next episode.

Venezuelan Woman
Do date Venezuelan women

What Destinations Would I Recommend?

I loved Germany. Berlin to be precise. Yet I could also spend years exploring Budapest. Heck most Central and Eastern European cities are fantastic places for digital nomads.

I almost considered moving to Colombia after landing here. It’s a great place for digital nomads. Yet the weather is terrible in Bogota and Argentina is my Graceland.

Buenos Aires is a digital nomads paradise. So, I might be returning to Buenos Aires mid 2023. And I’ve started discussing apartments with a real-estate agent in BA. Yet, I am buying an apartment in Bogotá (and I bought one in Peru!).

You’ll need to stay tuned to learn if I make BA my permanent home base. Or if I end up living in Bogotá.

View over Buenos Aires Argentina
Buenos Aires Argentina

Where Am I Now?

I’m in Bogota. And I will explore Medellin, Cali and Cartagena Colombia before I head back to Buenos Aires.

I’ve found I really like Colombians. They’re educated, reserved, polite and just downright friendly. And their country is absolutely beautiful.

Colombia gets a bad rap in my opinion. It’s a destination everyone should visit. And it has all of the necessary infrastructure and everything else a digital nomad could want.

This isn’t my first time in Colombia. And the purported dangers in Colombia have always seemed overblown in my opinion. 

Avoid digital theft – Always use a VPN as a nomad!

Where Am I Going Next?

I’ll be returning to Buenos Aires, Argentina. Before returning to Bogotá. BA is my Graceland and has everything I need in a city, but I just love Bogotá. And I don’t know why!

Che Graffiti Palermo
Street art in Buenos Aires Argentina

My best Moments So Far?

The day that I realized, I can make this digital nomad blogging thing work. And that I’d never need to go back to an office job. That’s the greatest moment so far.

The next best moments would be catching up with old friends. And making new ones along the way. As a ‘digital nomad’ or blogger you have the luxury of working when you want. And from wherever you want. You’re not tied to a specific work schedule or location.

You still need to work. And you’ll need to work hard. But you can have a life while working. You have the freedom of choice as a blogger. You’re unshackled from the location dependent 9-5. It’s a gift. 

View from Casa Mia
Working from a restaurant with a view in Havana Cuba

My worst Moments as a digital nomad living abroad?

Cuban hotel quarantine was less than pleasant. And being drugged in Cuba wasn’t much fun either. Yet neither was being stabbed in Bogotá. But there’s nothing that would stop me moving forward. There’s been no moment too grim.

I guess it’s likely a personality trait. And one that has helped me move forward at university and in general life. Nothing really stops me and I don’t take ‘no’ as a final answer.

If one door closes I pivot and go around the obstruction. I always get to where I want. I always work until I succeed.

Believe in yourself and treat everything like a problem with a solution. And you can get where you want to be, because nothing is impossible.

You just need to take large problems and break them down into bite sized pieces. Solving small problems is much easier than big ones.

So no, there really isn’t a worst moment. Occasionally I get my legs kicked out from under me. But I get back up and keep marching forward.

Kieran La Guarida
Digital nomad life – or death – In Havana Cuba!

Is Life Good As A Digital Nomad traveling the world?

The grass really is greener on this side of the fence. Life is better as a digital nomad. But if you have an unrealistic view of life and expect it to rain money without hard work, you’ll fail.

The key is to set manageable goals and just move forward. And anybody can do what I do. It’s the people who expect success without work or that look for shortcuts that fail.

If you’re prepared to put in the work and there’s something you’re passionate about, write about it online. You can monetize it later.

Just being passionate about something and being able to write about it yourself, means you can do what I do and you’ll succeed. I have this website, because I love to travel. But I also have, because I love writing about tattoos.

You can write about anything you have a passion for. And Google will do its thing and help your content find its audience.

Even if it’s geology and you want to write about rocks and dirt, as long as you’re passionate you’ll succeed. Just start writing about it online.

Then you can come across to the greener pastures of digital nomad life. It really is better, than the 9-5 office grind.

US Sanctions - Che Guevara - Revolution
Join the digital nomad revolution!

What Have I learnt In 2 Years Living Abroad?

I’ve learnt never to drink anything I haven’t opened myself. Or that I haven’t seen poured by the bartender. I’ve also learnt not to date Cubans. Thanks fanny and co.

Gifts for Cuban Women
Cuban Jineteras

How Do I Fund My Travels As a Digital Nomad?

My websites are monetised by affiliates links. With affiliates it costs nothing for people to buy products through my links. And they often get discounts for using my links.

I only recommend 5 things. Because I myself use them everyday. NordVPN, VisitorsCoverage insurance and WayAway or OMIO to book travel. Plus, I use a Wise Digital Account for my everyday payments and banking.

Wise is a digital nomad or expats best friend. Because it’s a borderless bank that gives the mid-market exchange rate and is fee free.

On my tattoo website, I only recommend the tattoo creams that I’ve used.

But if you feel like tipping me for this article or anything else on my site, you can drop a tip in my ‘tip jar’. I promise I’ll spend it on beer, whiskey, wine and travel.

Bar in Palermo Hollywood
Beer in Palermo Hollywood Buenos Aires

Did My University Degrees Help As A Digital Nomad?

My university degrees from the Australian National University, have better enabled me to understand politics and policy. And somewhat navigate foreign bureaucracy and different societies.

Yet, I wouldn’t recommend my degrees to an aspiring digital nomad. Or any degree really. What you really need is passion and persistence. If you like what you do and you can keep doing it without cutting corners, you’ll eventually succeed.

It takes months for search engines to pick up your website but once they do, your audience will find you. Social media and trying to pump content everywhere is just a distraction.

You don’t need all the fancy tools and courses that are sold online. You don’t need keyword research or anything else. The only thing that you really need, is passion and persistence.

The search engines are all semantic these days. They will understand what you’re writing about and they will find you an audience. Just start writing about what you love and don’t stop. You’ll succeed.

But if you did want to do a university degree, do something in IT. A university degree is not necessary, but it could help you in the longer term. I haven’t needed IT skills myself, but if you had them you might benefit.

Kieran University Degrees
Part of my collection of university degrees.

What Advice Could I Give To Aspiring Digital Nomads?

My only advice is that if you want to be a blogger or digital nomad, just start writing. You’ll get better over time. And your audience will find you.

Just start and don’t stop. Have faith and persistence and you’ll succeed.

It does take time and I wish I had started earlier. If I was still a uni student or planning travel, I’d start writing a year or two beforehand. The earlier you start your niche website and start writing, the earlier you achieve your goals.

Best VPN For Cuba
Working from a balcony in Nuevo Vedado, Havana Cuba 2023

How To Start As A Digital Nomad?

Start a website. Nothing fancy and just keep it simple. Then start writing and publishing. Everything else just works itself out.

Most articles online will overly complicate the process because they want to sell you a course or a piece of software. And if you fall into one of their rabbit holes you’ll lose weeks or months and whatever you paid them for the course.

Instead just start a basic website and start writing. Then just don’t stop. And don’t look for shortcuts. Shortcuts lead to failure. And so does comparing yourself to others who have been doing it longer.

Just start writing. Then keep writing and have faith. You’ll succeed.

Avoid digital theft – Always use a VPN as a nomad!

What is The Most Important Thing To Have As A Digital Nomad?

My four (4) essential items are my MacBook, my iPhone, NordVPN and Wise. NordVPN is the best VPN for digital nomads and it allows me to connect to the internet, as if I were at home. Wise allows me to be paid and to spend my money around the globe, fee free.

I also consider WayAway and OMIO essential for my own travel, but you needn’t travel. For my tattoo site, I could just stay in one place.

Nothing else is essential. I can blog in my birthday suit with those items, if I needed too. It might be awkward blogging in a cafe without clothes, but they aren’t essential.

As for traveling as a digital nomad, I packed way too much junk when I hopped that first flight. Keep things simple. If you’ve got a laptop, phone and a VPN, you can literally work from anywhere in the world. I do.

Avoid digital theft – Always use a VPN as a nomad!

Does Being A Digital Nomad Pay Well?

It goes up month by month, based on website traffic. And for seasonal topics and niches, it goes up one month and down the next.

But all in, you should be earning enough by the 8-12 month mark, to just keep doing it. And then the more content you make, the more traffic you get. And earnings keep going up.

Just start and don’t stop and the sky’s the limit. There’s plenty of bloggers out there making over 7 figures annually.

Right now, I make about half what I did in an office. But I’m living in places that cost less than a quarter of where I’d need to be, if I was back working in an office. So, I have double the spending power I had 2 years ago. 

Argentina Pesos at Dólar Blue exchange rate
Pesos in Argentina – learn about the ‘Dolar Blue’

What Am I Planning to do Next?

I’ll keep blogging and living the digital nomad life. I’d like to visit every country before I fall off this mortal coil. But, I also like to slow travel.

I spend 3 to 6 months at a minimum, in each country that I visit. And I’ll keep slow traveling because it allows me to really get to know the cities I visit and to experience the culture.

I’ll also be investigating apartments with a realtor in BA once I’m back in Buenos Aires mid year. And I’m in the process of buying a property in Bogotá. I’ve also bought one in Peru (2024). Because, I’ll need somewhere to store my junk if I ever make the mistake of accumulating any.

Remember, ‘the things you own, own you’.

Get a website, start writing about what interests you and get rid of the excess. Then you’re free to pursue the digital nomad life.

You will succeed if you start writing on a topic you’re knowledgable and passionate about. It doesn’t need to be a travel blog. You can write about and travel with a website on any topic.

Once you start writing, just don’t stop writing. And once you start traveling, you’ll never want to stop. The office views are much better as a digital nomad.

Sunset view from La Guarida
Sunset view from La Guarida