How We Quit Our Jobs to Travel Our Journey from 2008 to Now

The journey from conventional employment to a nomadic lifestyle is often romanticized, but the reality is far more complex. The transition requires immense courage, planning, and resilience.

This article chronicles the transformative journey of two individuals who, in 2008, decided to leave their secure jobs in Canada to explore the world. From initial doubts and fears to the ultimate realization of their dreams, their story offers valuable insights and inspiration.

A Backstory

Before embarking on their journey around the world, the protagonists held what society would deem ‘good jobs.’ They had secure positions in Canada, one working on the oil rigs and later as a heavy machine operator, and the other as a real estate legal assistant. Despite their ‘success,’ they felt a void in their lives.

They owned a condominium in downtown Calgary, drove a nice car, and enjoyed six-figure salaries. On the surface, their lives seemed ideal. However, beneath this veneer of success, there was a palpable sense of dissatisfaction. The protagonist’s job was particularly grueling, filled with toxic work culture and a stifling environment. Ten days of annual leave were hardly enough to explore any meaningful travel, aside from short resort vacations. The other protagonist fared slightly better, enjoying her workplace more but still feeling the relentless grind of the nine-to-five routine. Their sense of unfulfillment grew, fueled by the repetitive nature of their work and the realization that there was more to life than their current existence.

The Lightbulb Moment

The epiphany struck during a brief, all-inclusive holiday in Mexico, a common getaway for North Americans. It was an ATV tour that triggered a profound realization. While they had initially intended to follow the usual tourist activities, they found themselves yearning for a deeper connection with the local culture. Passing by a village, they realized they wanted to engage more meaningfully with the world.

This fleeting experience planted a seed of change. They began to envision a life beyond the confines of their high-stress jobs. The idea that there was a world worth exploring full-time took root. Upon returning to Canada, these thoughts refused to fade, and they found themselves increasingly restless in their old routines.

The Decision to Quit

The moment of decision came a few months after their Mexico trip. One particularly harsh day at work became the catalyst. Frustrated with the relentless grind and toxic environment, the protagonist started researching the concept of ‘backpacking’ and discovered the idea of taking a ‘gap year.’ The revelation was both exhilarating and daunting.

Upon sharing this newfound passion with their partner, the response was immediate and affirmative: ‘Southeast Asia.’ This set the wheels in motion. Over the next ten months, they worked tirelessly, saved money, sold their possessions, and planned their adventure. The idea of quitting well-paying jobs was terrifying, but the fear of living a life unfulfilled was even more daunting.

The Strain Before Departure

In the months leading up to their departure, the stress was palpable. Selling their home, working exhaustive hours, and planning a year-long trip took its toll on their relationship. They argued frequently, the tension rising as their departure date approached.

Despite these challenges, they persevered. On November 17, 2008, they boarded a plane, leaving behind the stability of their old lives for the uncertainty of new adventures. The act of leaving was laden with a mix of relief and apprehension, but it was a crucial step towards the life they envisioned.

Adaptation and Realization

After their first year of travel, which extended into 13 months, they returned to their former jobs in Canada to save for another trip. This time, their journey was even more ambitious, encompassing multiple continents. However, as the second trip neared its end, the familiar dread of returning to their old lives resurfaced.

The realization struck that they could not revert to their previous lifestyle. The notion of living in a static environment contrasted sharply with their newfound love for exploration. Determined to find a sustainable way to travel indefinitely, they vowed to make this lifestyle permanent.

In a particularly emotional moment on a Thai beach, the sense of urgency crystalized. They scoured the internet for opportunities to earn money on the road, eventually stumbling upon teaching English in China. Despite lacking university degrees, they decided to take a chance, leading to a life-changing opportunity.

Finding Remote Freedom

Once in China, they were proactive in their job search, emailing various schools and eventually securing positions at Shane English School in Yangzhou. This experience was transformative, providing both financial stability and a deeper cultural immersion.

During this period, they began a blog, initially as a means to share their travels with friends and family. Inspired by another travel blogger, they committed to developing their blog seriously. Though progress was slow initially, their persistence paid off, and their blog began generating income.

Their success grew over time, with the blog evolving from a modest endeavor into a substantial business. It afforded them the freedom to travel and work from anywhere in the world, turning their dream into a sustainable reality.

Reflections on the Journey

Looking back, they express astonishment at how their blog transformed their lives. The business now runs on autopilot, offering them financial security and the freedom to pursue their passions. They are grateful for the opportunities and fulfillment this lifestyle provides.

Their experience underscores the viability of turning one’s passions into a sustainable business. The journey from traditional nine-to-five jobs to remote entrepreneurs was fraught with challenges, but the rewards have far exceeded their expectations. Their story illustrates that with determination and adaptability, one can create a life aligned with their deepest aspirations.

Concluding Thoughts

Reflecting on their journey, it’s evident that the decision to leave their jobs and travel was transformative. The initial fear and uncertainty gave way to a fulfilling and sustainable lifestyle.

The pursuit of remote freedom required resilience and adaptability, but it ultimately enabled them to live a life rich in experiences and personal growth. Their story inspires others to consider the possibilities that lie beyond conventional paths.


Looking back, it’s evident that leaving secure jobs for a life of travel was a pivotal decision. The journey was fraught with challenges but led to profound personal growth.

This pursuit of remote freedom exemplifies the notion that life beyond conventional boundaries is not only possible but immensely rewarding.

Source: Goatsontheroad

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