Chapter 1: Reflections on a Turbulent Year

During my initial year of post-secondary education, I barely managed to secure a single philosophy credit before I decided to drop out. This year of uncertainty saw me move no less than four times.

Each relocation taught me valuable lessons, but the experience became increasingly destabilizing. During three of those moves, I reconnected with old roommates from Western Canada, while two of them found the culture and climate of Ontario too challenging and chose to return home. I stubbornly resisted the urge to retreat and opted to stay.

The memory of that year is etched in my mind as one filled with anxiety. It wasn't until I found a stable job and housing that I could finally settle down and start living fully. At that time, I was just beginning my journey into independent adulthood, and I lacked confidence in my capabilities. I needed tangible proof of my competence before I could trust myself.

In 1990, I met the woman who would become my wife. We married in 1993 and welcomed our first child in 1996. Since then, I have remained in one place. Like many others from the West, I began to feel alienated by the structured workplace in Ontario and sought alternative paths. My interest shifted to finance and investing, leading me to literature about tax exiles. One way to achieve this status is by becoming a perpetual traveler, a pursuit that necessitates resources and ideally, a portable skill set or international business.

This was long before the onset of the digital age, and I encountered inspiring stories of those who had achieved their version of freedom. Many were influenced by libertarian ideals, framing their experiences as noble struggles against a controlling society. Ayn Rand's philosophies had a significant impact on these narratives. However, they also revealed a profound sense of loneliness—missing family gatherings and watching grandchildren grow up from afar.

A tangible absence of community and connection permeated their lives. They often spoke of the emotional toll of constantly being the outsider, forced to leave in order to maintain their tax status. Despite the benefits of their lifestyle and financial success, they acknowledged the personal costs of alienation. This candidness was comforting in its authenticity.

In contrast, contemporary writings about digital nomadism lack this level of honesty. While I grasp the surface reasons for this lifestyle—such as rising housing costs, declining living standards, the vanishing middle class, and student debt—there seems to be a deeper, unspoken narrative.

While individual motivations for becoming a digital nomad differ, I find the gaps in these articles lead to more questions than answers. For instance, who is financing these adventures? Did they simply board a plane? My extensive travels have never been free. It's often unclear whether the individual is retired, has sold a business, or is working remotely. Did their digital income require a certain level of stability before they went abroad? Many young individuals claim to be digital nomads, but I wonder how many are relying on parental support. Some boast about their "roughing it" lifestyle in hostels, yet as someone who has recently retired, I can assure you that uninterrupted sleep becomes a priority.

Family and cultural ties often go unmentioned. Leaving home for the first time is emotionally challenging, no matter your age. If you have never immersed yourself in a culture with a different language, you will likely face awkwardness and adjustment challenges. Are you committed enough to escaping the North American grind to learn a new language? If not, you may forever remain a long-term tourist.

I know several friends who abandoned their North American lives to travel. One, who was on a trip with his then-fiancée, saw their relationship end during the journey. He struggled to regain his career momentum and had to start anew at an entry-level position. As a result, he now faces the prospect of working into his late sixties before retirement. While not the end of the world if you enjoy your work, it serves as a reminder that choices have consequences.

When expats and nomads share tales of endless cycling, snorkeling, and hiking, I can't help but question what their lives were like prior to their departures. Did they lack meaningful family, friendships, or relationships? Family alienation is a genuine issue, but so is the emotional labor of building new networks of support that were absent in one's upbringing. The pandemic has underscored that we are inherently social beings, more than we may have previously recognized.

A colleague of mine maintains connections with an online ex-pat group based in Latin America. Unfortunately, many of their discussions have devolved into political rants about right-wing ideologies. Ironically, many of these individuals once participated in public sector unions that negotiated the pensions and benefits which enabled their retirement lifestyles, yet they now criticize the very systems that afforded them their freedom.

As with many intentional communities outside the traditional workforce, there are those who seem to have forgotten their roots and lost their sense of purpose. The line between non-conformity and an inability to coexist with others is thin.

Some individuals engage in excessive drinking throughout the day. The impact of immigration transforms both the newcomer and the host country, both visibly and experientially.

One former roommate embarked on a trip to Australia with his then-girlfriend, only to break up during the journey—a recurring theme, indeed. His story deserves its own exploration, as he became remarkably successful in a business unrelated to digital nomadism. Yet after more than a decade in Asia, he invested in a vacation home in California, seeking a connection to his North American roots. No matter how hard we try, our culture and upbringing are not easily discarded.

As I approach two years into retirement, my children are beginning to carve out their own paths. I feel a compelling urge to make a significant move abroad. Escaping the winter is a strong motivator, as is the desire to broaden my understanding beyond my Canadian experiences. Unlike the unsettling times after I left university, this decision will be entirely mine.

Every significant life transition involves moving toward some goals while stepping away from others. However, the narratives we receive about digital nomadism and expat life often fail to provide a complete picture.

Chapter 2: The Emotional Costs of Nomadic Living

Video Description: This video explores the ethical implications of the absence of the human element in moral reasoning about AI weapons, highlighting the importance of human connection in decision-making.

Video Description: This video delves into the emotional nuances of absence, scarcity, and apathy, particularly in the context of no contact scenarios, emphasizing the psychological impacts of separation.