My Second Year Working as a Digital Nomad

Some of you might remember an article of mine from a year ago in which I praised the incredible freedom afforded to me by working as a digital nomad? The article was overly-positive and well received so I decided to do a more sobering follow-up. 

In my second year of digital nomading, I was exposed to the darker side of this largely unregulated, risky and often confusing lifestyle choice. Looking back on my first year I can see now just how lucky I actually was and how, as a result, I became overconfident. Throughout my second year on this journey, I often found myself recalling a lyric from the Cypress Hill song “(Rock) Superstar”: “Save your money, man, save your money…”

We left off last time just as I was ready to embark on my first real test as a traveling digital nomad. Yes, admittedly I had just cycled through Africa while still working online almost daily but Africa is cheap. Heading into the expensive countries of northwestern Europe while earning a meager digital nomad salary proved to be an entirely different challenge.

Scandanavia, May 2019.

My first port of call was Stockholm, one of the most expensive cities in Europe. Fortunately, it was part of a cruise package that I had already paid for, so I had a smooth introduction.

The cruise went well and I had a great time visiting Finland, Russia, and Estonia. Despite having no wifi on board, I was able to get all my work done over mobile data because we docked each night at a city port. I would wake up early every morning, stumble hungover to the breakfast area and work tethered to my mobile phone. 

Working from the cruise ship

After the cruise, I began a two-week cycle trip from Stockholm to Copenhagen. Accommodation in Sweden is very expensive so I knew that I would be camping all the way. Fortunately, due to the ‘Allesmansvretten’ law, Sweden is one of the best countries in the world for free camping. However, I immediately faced some issues: the temperature dropped to near zero at night and since I had been out of the UK for too long, my free EU-roaming had been disconnected. Fortunately, purchasing a Swedish simcard was simple enough and there was always a McDonalds with free wifi that I could use for the cost of a €1 coffee.

So I bought some warmer clothes, enjoyed some awesome cycling, and met up with several old friends. Things were going well until the last day of my cycling trip when my biggest client suddenly canceled all work because of a Google update. Due to a change in a GoogleAds algorithm, certain websites no longer showed up well in search results and the company lost tons of traffic. They couldn’t afford to keep the sites going.

Working from McDonald’s, Sweden. June 2019

London summer

I had some savings, of course, but it was a huge loss of income and a complete surprise. It made me suddenly very aware of the fragility of both my business model and my clients. What made it even worse was that I had to go to London in a few days to renew my documents and I knew saving money there would be impossible.

Fortunately, my old hometown provided a wealth of free accommodation from family and friends. I soldiered on, struggling to find new work while going out often and spending far too much. Several times I contemplated throwing in the towel and applying for a real job but thankfully I persevered. Shortly before I was scheduled to leave London I had luckily managed to save up just enough cash to keep traveling.

Eastern Europe, July 2019

In late July, I returned to Sweden to collect my bike and continued south through eastern Germany, briefly visiting friends in Berlin before hitting Hungary. I had managed to scrape together enough work by now that I was just about breaking even each day. Hungary is cheap as chips so I had an amazing time in Budapest before continuing on to Romania.

My cycle trip in Romania was interrupted when I made some friends in Brasov and decided to stick around for a few weeks. I loved Brasov so much that I even began investigating the possibility of living there with the aim to return once I had completed my trip. It was now almost August and I had secured enough work that I was making decent money. However, I clearly hadn’t budgeted properly for the road ahead.

A cafe in Sighisoara, Romania. July 2019

Croatia, Greece, and Burning Man, August 2019

Due to bad planning on my part, I had tried to squeeze way too many things into August. First I would go to Modem Festival in Croatia then immediately onto an expensive week in Greece before flying to California for Burning Man. It was all too much, too close together, and not only did it cost too much but it meant I did very little work in August.

By early September I was nearly broke and crashing on a couch in San Francisco. The accommodation was kindly gifted to me by a friendly burner, his phone number still scrawled in permanent marker on my forearm since day one of the Burn. With the last of my cash, I managed to make my way back to Paris and then on to Berlin where I spent a month bouncing between friend’s sofas.

As I turned 37 that month, sleeping on a single mattress on the floor of my friend’s kitchen, I realized that digital nomading is not all beaches and cocktails.

“Save your money, man, save your money…”

My view from the kitchen floor, Berlin. September 2019

Travel, interrupted.

Fortunately, I did find more work, saved some money, and could continue on my travels for a bit. After completing the rest of my cycle trip through Serbia and Bulgaria, I went to visit my parents in Cyprus. Initially, from there the plan was to continue south from Egypt through East Africa and complete the second leg of my Cairo to Cape Town cycle route.

However, the experience in Europe had jarred me and I no longer had the reckless abandon which previously would have sent me unprepared into Africa. With a weakened spirit and my first self-employed tax deadline looming, I threw in the towel and returned to South Africa to figure out my future.

It was fortunate that I did because soon after returning another client of mine went bust, leaving me with two weeks of unpaid work for which I’ve never been compensated.

Tax hell

Just before Christmas, I decided to save money by completing my first ever tax return all by myself. DON’T DO THIS. PLEASE FOR THE LOVE OF GOD DO NO TRY TO DO THIS!

Needless to say, I got so many things wrong that the tax office probably thought I was attempting tax evasion before speaking to me on the phone and realizing I was far too stupid for such advanced trickery. In the end it all worked out okay but I wasted about two weeks fixing it and the stress probably took a few years off my life. Trust me, just get yourself an accountant.

All in all, it worked out for the best because if I hadn’t returned home I would be quarantined somewhere in Sudan right now. I still love my digital nomad lifestyle more than ever and couldn’t possibly consider returning to a desk job – I just need to figure out how to make it more secure, streamlined, and profitable. 

Luckily, mother nature has forced me into a position to do just that.


  1. A fascinating story of a true digital nomad!
    Loved your post.
    People must know the cruel experiences you went through in your life as a digital nomad!
    Best wishes for your upcoming exciting trips. 🙂


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