Leaving Corporate America

At 46 years old, Jason Bennett reflects on a successful, yet ultimately unfulfilling, career as a senior marketing director for Banana Republic in San Francisco. Despite earning a comfortable salary and receiving considerable bonuses, Bennett felt increasingly disconnected from both his professional life and the city he called home.

“I started to feel a disconnect with both my job and my city,” Bennett shared. “I started to wonder if I really wanted to spend the rest of my life in an office working for other people.”

Embracing Change

In 2015, Bennett decided to make a significant life change. After careful consideration and financial preparation, he resigned from his position and founded True Star Consulting, a marketing firm designed to assist brands with strategic planning and creative direction. Having saved enough to support himself, Bennett embarked on a new adventure, relocating to Lisbon while running his business as a digital nomad.

His travels took him to Medellín, Colombia, in 2016, where he envisioned a more permanent home. Two years later, he made the move.

The Rising Trend of American Expats

Bennett’s journey reflects a growing trend among working professionals. According to the Federal Voting Assistance Program, the number of U.S. citizens residing in South and Central America and the Caribbean increased from 374,241 in 2012 to 429,674 in 2022, with many seeking career opportunities outside the United States.

“It was one of, if not the best, decisions I’ve ever made,” Bennett stated. “It always felt like home.”

A Solid Financial Foundation

Born and raised in San Francisco, Bennett earned his bachelor’s degree in business administration from the University of Oregon in 2000. Early on, he was proactive about his finances, heeding his grandparents’ advice to maximize his 401(k) contribution before indulging in personal pleasures.

In 2012, he purchased a one-bedroom condo in San Francisco, opting for a 15-year mortgage to build equity and secure a lower interest rate. His investments included stocks and fixed-income securities, and he has meticulously tracked his finances since he was 17 years old. This financial discipline gave him the confidence to leave a consistent salary for the uncertainty of entrepreneurship.

“I didn’t know I was going to do this when I was 25,” Bennett said. “But I did know it was important to save.”

Lifestyle in Medellín

Since his relocation, Bennett has enjoyed a vibrant lifestyle in Medellín, appreciating the city’s favorable climate, rich culture, and affordability. He noted that his daily expenses have significantly decreased compared to San Francisco, allowing him to enjoy “excellent meals” for under $10 and quality coffee for less than $2.

Bennett, who remains single and child-free, has also founded “The Paisa Plan,” a tourism company aimed at helping visitors explore both Medellín and Colombia. Additionally, he lends his marketing expertise to the Medellín Philharmonic Orchestra, demonstrating his commitment to the community.

“It reflects my love, respect, and appreciation for my adopted home,” Bennett explained.

Finding Balance and Motivation

After six years in Medellín, Bennett appreciates a better work-life balance compared to his previous life in San Francisco. He enjoys the city’s energetic atmosphere, its culinary diversity, and the abundance of parks and cultural events.

“I also take every opportunity to explore the city and immerse myself in what it has to offer. There are so many excellent restaurants and cafés. More stunning parks than you can count. And there is always something happening culturally,” he remarked.