One Day in the Life of a Digital Nomad

My current journey is a tricky one to say the least. On July 14th, 2022, when I severed ties with my home country, Canada, I was fulfilling a 27 year old promise (yep, a real down-to-earth promise) of seeking out warmer pastures. At the time when I made that decision, climate was the only thing on my mind. 

From cold weather to technology

It was during the winter of 1996 when I was eating my lunch inside my completely frozen 1991 diesel Jetta with over 400,000 km that I suddenly and most abruptly decided that Canada was no longer for me. After all, who in his right mind, would go to the Ottawa University parking lot on his lunch break on a windy -35°C (-31°F) day to start his diesel engine and heat it up for an hour while eating an almost frozen sandwich for fear of not being able to start the car at 5pm? This was indeed the day that was going to, unwittingly I admit, instigate my current up-hill battle. There isn't a day on my current journey that I don't sympathize with Sisyphus.

Of course, I don't feel any kind of hideous punishment by Zeus regardless of my beliefs nor do I see my current efforts as futile labor. The fact that all kinds of mishaps have occurred since I've embarked on this digital nomad journey is objective. I can't dispute it. How I feel about those events is purely subjective and controllable as I remain at the wheel driving this journey.

I may be a non-resident of Canada, theoretically homeless, living from Airbnb to Airbnb, armed with limited Spanish and without health insurance but I am moving slowly and hopefully in the right direction, albeit extremely slowly, as I steadily overcome the shock of my obvious lack of preparation. 

I tell myself that my current reality is a journey and I'm at the beginning of that journey slowly putting in place the chess pieces that will allow me to thrive in the coming years. For sure, the obstacles are there. I can passably communicate in Spanish but I can't really understand much of it. Also, I need health insurance---at age 58? Hum, we'll see about that won't we? For now, let's just call it self-insurance stemming from my questionable life savings and then there's the problem arising from being a resident of...well...nowhere. Who would have known that being a resident of no country could cause a few financial pickles? Perhaps the most difficult, thus far, has been the issue of relationships. Being on the road all the time is not conducive to easy relationship-building. Naturally, there's WhatsApp and Facebook Messenger but when you're on a journey where you need to thread the needle day in and day out, there isn't much time to socialize for very long. You need to plan and build. You need to get work done; learning about the country you're visiting, doing videos for your YouTube channel, researching potential solutions to existing problems (and trust me, there are plenty of those) and ultimately researching your next destination in the hopes of eventually finding a home that can be more stable.

It's not like I hadn't done any kind of preparation. I had several years to prepare in fact. However, I now realize, as I suspected weeks before my departure, that the internet would only be partially helpful. You can't, after all, research what you don't know you need to research (or let's just label that it Rumsfeld's Unknowns):

"...as we know, there are known knowns; there are things we know we know. We also know there are known unknowns; that is to say we know there are some things we do not know. But there are also unknown unknowns -- the ones we don't know we don't know." 

- Donald Rumsfeld

Who would have known, right? In any event, my first country in my long list of countries to visit after leaving Canada, was the Dominican Republic. I chose that country strongly suspecting that it would not be my final destination. At least, I got that part right. The idea, initially, was to research the possibility of getting residency on the colorful island. It was a great idea but I'm not just a beach and nature lover, I also have an affinity for technology. Spending my entire life in high tech did not just happen by accident. (Ok, well actually it did.) In fact, I just happened to ride what was to become the home computer wave of the early 1990s which ended up handing me a high tech career on a silver platter. Little did I know at the time that technology was going to become a second criteria for a destination country. 

The bottom line is that my relationship to technology is what prompted me to cross off the Dominican Republic from my list of potential retirement destinations. That and the constant street noise which motivated me to bring along with me the ear plugs I had when I was in the army. Unfortunately, the D.R. is just not known for its stable internet infrastructure yet and while it's easy enough to obtain high internet speeds, the reality is that it's highly inconsistent and prone to frequent drops in performance. I'm not entirely sure if it has anything to do with the country's wiring infrastructure but the end result always seems to be the same. All the same, I'm confident that this Caribbean nation will eventually become a powerhouse in its own right competing with the likes of Mexico and Colombia but just not at this time.

So while I may have given up on the beautiful island, I am not ready to leave without learning a few more things about life here. I just completed a 4 week stint in Bávaro where I quickly came at odds with a few unexpected surprises most of which, let's face it, are part of the nomadic lifestyle. I'm nothing if not somewhat flexible but it doesn't mean I shouldn't consider other locations on the island to see if things fare better. 

Santo Domingo calls on me

Therefore, my next stop was the city of Santo Domingo. I took the bus from Friusa (a district of Punta Cana) and began an almost 3 hour trek where I would witness incessant arguments among the locals regarding seat assignments. (So that's what 42B meant on my ticket). The good thing about understanding little Dominican Spanish is that my facial expressions remained quite nonpartisan while witnessing the debacle.

     "Oh well..." I thought to myself. "Just another day at the digital nomad homeless office." That would prove to be less true, however, upon my arrival in Santo Domingo when I asked the driver if this was my stop. He didn't know so I got off. I must admit, I was a little weary about leaving my 70L backpack and my small carry-on (with my laptop) in the baggage compartment as people were getting off the bus and collecting their luggage from the compartment. 

As soon as I got off the bus, I felt it. I knew something was wrong and it took only seconds for my spidey senses to kick in. There were no street signs and according to my smartphone, there were no public wifi hotspots and to make matters worse, I had no data plan. So yeah, I started to worry about my next move.

I began walking around what appeared to me as a dangerous neighborhood with 70L on my back and wheeling around a small carry-on along broken sidewalks searching for street signs. If I could, at least, come across some street signs, I might be able to determine where I was. Honestly, in hindsight, I didn't really know what I was doing. I wasn't thinking rationally. I was thinking emotionally. I was still trying to process the pickle I suddenly found myself in. Have you ever felt as though you were in a situation without any obvious exit? Actually, there were plenty of exits but I just wasn't seeing them because I was overwhelmed by the sheer cultural shock of what I was witnessing. I had never seen such a poverty-stricken neighborhood before. Little did I know.

     "No street signs? Seriously?" I asked myself. "Okay but what does that mean for me?" After walking around for about 30 minutes I finally came across a park and slowly began to get a grip on myself. Minutes after I sat down on a bench and began a selfie video (for a future YouTube upload), a little boy, who had undoubtedly wandered off while his parents were socializing with the park's homies, came, sat next to me and inserted himself into my vlog apparently eager to make his presence known to the world.

Of course, never underestimate a child's curiosity for the unknown. In all the excitement worry, I was somewhat unaware that the park's welcome committee was playing with my Rode wireless mike and turned it off as I was recording my video until much to my surprise, when I later revised my video, I realized the video had no sound. Be that as it may, it was the cost I had to pay to get myself out of my current predicament. The boy was going to help me out in a rather unexpected way.

In a country where mobile phones are the next best thing to expressos and café con leche the boy sure knew a lot about wifi and the art of getting free internet access. As soon as he saw the wifi scan result of my phone he immediately pressed on one of the hotspots, intentionally or otherwise, as though it was his own personal wifi hotspot. Naturally, it didn't connect because in the Dominican Republic, open wifi is not very popular since, I would later find out after speaking to an employee at the popular Santo Domingo Coffee franchise (similar to Starbucks and Second Cup), sharing wifi as a hotspot is billable and generally not given out so freely by businesses. Most establishments will give you access to their wifi but you have to ask for it. 

I would eventually realize that the hotspot actually belonged to the bus terminal behind Parque Enriquillo where, lo and behold, I was sitting. Why hadn't I noticed that before? Because hotspots are not always labeled after the business establishment offering it.

It was only at that point that I actually saw a ray of hope. Okay, so I wasn't really in any danger. If necessary I could have hailed a cab and simply handed him the address to my fine abode in the Piantini neighborhood with the hope that he wasn't going to take me for a ride (literally) and drop me off in the Los Guandules neighborhood, where drugs are more easily acquired than bottled water. 

Sure, I might have made it to my Airbnb unscathed--me, a snowflake-looking tourist hauling 70L of goodies on his back and while wheeling an extra carry-on for good measure. Yeah, no, I wasn't thinking of all that. I was a model of zen centeredness hence my desire to get onto a public wifi so I could get myself a Didi (cheaper competitor to Uber).

After finally tuning in to the idea that free wifi was just a few steps behind me, I casually strolled over to the bus depot and made my way inside the sardine container with my luggage and asked one of the staff members, in my broken yet surprisingly good Spanish accent, if I could get access to their wifi.

Moments later after ordering my lift on Didi, I happily hopped into the car after confirming that the driver was indeed Darwin and proceeded to my destination.

My first few steps in Santo Domingo were clumsy mostly because I'm not here as a tourist but rather as a Digital Nomad trying to start a new chapter after a couple of decades of hustling in the high-tech sector. The path as a tourist is remarkably different than the path as a nomad. Tourists travel in hotel buses waiting at the airport to take them to their all-inclusive. Nomads seek out the cheapest way to travel without getting ripped-off while getting to their hopefully clean room which includes nothing but a bed and linens.

Years previously, when I travelled as a tourist, I would see the window-dressing of a country. Now I see the harsh reality of what's behind it.

When you travel as a tourist, you have a support structure around you. That is, resort employees that shield you from reality and ensure that you have only the most awesome memories so that you have something to look forward to when you're back at your mind-numbing desk job in the middle of winter on a grayish looking day.  I speak from experience of course.

I admit, as a beginner nomad, I find myself contemptuously figuring things out as I stumble along from the seat of my pants occasionally drawing motivation from when I was working at a desk job and reminding myself of all those end-of-the-day stress-riddled events that gave me those all-to-frequent back aches no matter how ergonomic my chair was.

The path I am travelling as a beginner nomad is colorfully decorated with the unexpected requiring patience and consistency as a response.

Then again, success is often merely persistence in disguise. Day in and day out, I convince myself that I'm a novice nomad although much less today than yesterday. So, the journey continues.