In 2016, I spent two transformative weeks in Medellín, Colombia, which significantly altered my life’s path.
During my time there, I immersed myself in the local culture, hiking to breathtaking waterfalls and experiencing Latin music. But it was the small moments — the tropical fruits, and the lively conversations in neighborhood barbershops — that resonated with me the most. After returning to Canada, I couldn’t shake off the allure of Colombia. This compelling experience spurred me to create a bold plan: to become a freelance writer and relocate to Colombia.
At that time, I was in my mid-20s, living in Toronto and working in the magazine industry. Not having deep roots in the city, combined with an anticipation of job changes, made this the perfect moment for me to take a leap of faith.
Over the next two years, I networked, built a clientele, and saved diligently. Eventually, I returned to Colombia to fully embrace freelance writing, aiming to immerse myself in its vibrant culture and learn the Spanish language.
Fast forward eight years, and I now reside in Ecuador, continuing my journey as a freelance writer. The move was undeniably successful, yet there are several aspects I would approach differently, with the benefit of hindsight.
Strategies That Worked for Me
Understanding the importance of financial stability, I meticulously researched the cost of living and saved for around a year before making the move. The creative industry can be rife with uncertainty, particularly with the current challenges posed by AI and an oversaturated market.
I realized that I needed to secure my finances before diving into this new adventure, so I aimed to save approximately $8,850, covering my expenses for a year. I reached this goal through freelance writing during my evenings and weekends and simplifying my living conditions.
Once in Colombia, I was fortunate enough to work while exploring the beautiful landscapes of the coffee region. I discovered the joy of working on meaningful projects that were both satisfying and financially rewarding. I’ve since adopted three client criteria that guide my decision-making: enjoyment in collaboration, meaningful work, and fair compensation.
Lessons Learned for Future Expats
Pursuing a path like mine comes with its own set of challenges, and if I could offer advice to others seeking a similar journey, here are a few things I would do differently:
1. Prioritize Learning Spanish
Having developed my Spanish to an intermediate level, I now acknowledge its considerable impact on my professional endeavors. Writing travel stories that resonate with Ecuadorian culture often requires conversations and interviews in Spanish. In retrospect, I wish I had dedicated a more focused period to solely mastering the language when I first arrived.
2. Engage With Local Communities
As a remote worker, I recognize the privilege I hold in being able to earn in one economy while spending in another. This dynamic has motivated me to give back to the local communities that have enriched my experience. Moving forward, I plan to engage more deeply by supporting local causes, either through my time or financial contributions.
3. Showcase My Work
For years, I let self-doubt hold me back from creating a comprehensive portfolio. However, upon finally doing so, a wealth of opportunities emerged. I learned the importance of promoting my work, and the realization that I undervalued my own capabilities has empowered me to reach out and network effectively.
4. Embrace Freelance Flexibility
One of the major advantages of freelancing is the freedom it provides. Reflecting on my past, I recognize the vibrant hustle I experienced during my early days in Medellín. I wish I had taken greater advantage of my flexibility, allowing myself to travel solo and explore more regions within Colombia.
The journey that began with a short visit to Colombia has blossomed into a gratifying writing career. Now, in my mid-30s, I find myself living in a beloved region of Ecuador, fulfilling a dream that emerged from a spark of inspiration. If you’re contemplating a move or a career change abroad, I encourage you to pursue it wholeheartedly.
If you have your own story about living abroad, feel free to reach out to the editor at akarplus@businessinsider.com.
Transformative Journey: From Toronto to a Freelance Career in South America
In 2016, a two-week trip to Medellín, Colombia, sparked a profound change in my life. Immersed in the vibrant culture, I was captivated by the sights and sounds, from unique Latin music to the delightful flavors of local tropical fruits. The essence of community shone through in neighborhood interactions, making it hard for me to forget Colombia’s charm once I returned home to Canada.
With the desire to become a freelance writer and relocate to South America, I began laying the groundwork. Living in Toronto and working in magazine publishing, I realized I had a unique opportunity. With no deep ties to my surroundings and the feeling that a career shift was imminent, I knew it was the perfect moment to take a leap of faith.
Over the next two years, I diligently cultivated my professional network, secured clients, and saved money. Finally, I returned to Colombia to embrace the freelance lifestyle, excited to immerse myself in the local culture and learn Spanish.
Eight years have passed, and I now reside in Ecuador, continuing my career as a freelance writer. While the journey has been fulfilling, reflecting on my experiences, I recognize that there are several aspects I could have approached differently.
Successful Strategies for Freelancing Abroad
One key factor to my success was thorough research on the cost of living and saving strategically. Creative work can often present challenges, with fluctuations in the market and the ever-present threat of new technology impacting our fields. Understanding this, I saved enough to cover my expenses for a year, which amounted to roughly $8,850. Achieving this goal required careful budgeting, and I supplemented my income by writing freelance articles in my spare time, working at a running magazine during the day.
Lessons Learned: Hindsight and Reflection
Reflecting on my journey, there are three vital lessons I wish I could share with my younger self embarking on a similar adventure. Firstly, I would emphasize the importance of dedicating focused time to mastering Spanish. Now at an intermediate level, the language has proven invaluable for my travel writing. Initially, I was eager to dive into every aspect of my new life, but had I concentrated solely on language acquisition, my cultural integration would have accelerated significantly.
Another lesson is the need to give back to the local community. As a remote worker, I had the privilege of earning in one economy while spending in another; however, I believe it’s vital to contribute positively to the community that supports us. Moving forward, I would commit to a deeper, ongoing involvement in local causes, giving back either through time or resources.
Embracing Opportunities and Flexibility
Lastly, I realized I had been holding myself back by not showcasing my work. After finally establishing an online portfolio, I began receiving new opportunities, including a significant assignment with a prominent travel editor. This experience taught me the value of taking initiative and presenting my work confidently to potential clients.
Embracing the flexibility of freelance life has also been rewarding. The freedom to define my own work schedule has been incredibly empowering. I urge fellow freelancers to harness this flexibility to take spontaneous trips or undertake new experiences that can inspire creativity and growth.
My journey, which began with an adventurous spirit, has evolved into a rewarding career in South America. Now, in my mid-30s, I find joy in living in a place I love while pursuing my passion for writing. For anyone considering a similar path, remember: the journey might be uncertain, but each step brings learning and growth.

