A Gen Xer quit his corporate job in SF and moved to Colombia. He said Medellín is more affordable and he’s been able to launch 2 startups.

Jason Bennett, 46, moved to Medellín, Colombia, from San Francisco in 2018.

Jason Bennett had a successful career in San Francisco but didn’t see a future for himself in the corporate world.

Bennett, 46, worked as a senior marketing director for Banana Republic. He earned a good salary and received great bonuses but felt unfulfilled.

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

In 2015, Bennett quit his job at Banana Republic and founded True Star Consulting, a marketing firm that specializes in strategic planning and creative direction for brands. He said he had saved enough for the future and was ready to start a new adventure at the age of 37.

At that time, Bennett moved to Lisbon and began running True Star Consulting as a digital nomad. In 2016, he visited Medellín, Colombia, and said he envisioned it as his future home. He relocated there two years later.

While many Americans are moving abroad for retirement, Bennett is among the working professionals seeking a career outside the US. According to data from the Federal Voting Assistance Program, which helps overseas citizens vote in US elections, 429,674 US citizens lived in South and Central America and the Caribbean in 2022, up from 374,241 in 2012.

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

Jason Bennett, 46, looks over Medellín, Colombia, where he moved in 2018.

Building financial independence started at a young age

Bennett was born and raised in San Francisco. He earned his bachelor’s degree in business administration from the University of Oregon in 2000.

After college, Bennett worked in marketing at the department store Mervyn’s before joining Banana Republic in 2004. Over the next decade, Bennett ascended through the corporate ranks, becoming a director of marketing in 2013 and a senior director shortly after.

While Bennett enjoyed his job, he said he felt unsatisfied with his day-to-day work. He wanted to take ownership of his schedule and career growth.

“At the end of the day, I wanted to be my own boss,” he said.

Bennett said the prospect of quitting his job at Banana Republic seemed reasonable because he had been actively saving and was diligent about his finances.

“Very early on, my grandparents told me to max out my 401(k) and then go have fun, and that’s what I did,” Bennett said. “The lesson of compound interest should be topic No. 1 for anyone thinking about one day charting their own path.”

In 2012, while still living in San Francisco, he bought a one-bedroom, 700-square-foot condo for under $400,000. Bennett said he chose a 15-year mortgage to accelerate his home equity and lock in a lower interest rate.

Bennett also grew his wealth through investing in stocks, index funds, and fixed-income securities like certificates of deposit. He’s been keeping detailed track of his finances since 1995, when he was 17 years old.

Bennett said he felt confident to quit his own job to earn a fraction of the salary at his own company — and he felt confident to move abroad. He declined to share what his company books in revenue.

“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.”

Life in Medellín compared to San Francisco

Bennett said life in Medellín is incredible, from the weather to the culture and food.

He said his cost of living is much lower than in San Francisco. For example, he said he can have “excellent meals” for less than $10, and a cup of “the world’s best coffee” for less than $2. He also said public transportation and Uber are inexpensive

Jason Bennett said the coffee in Colombia is the “world’s best.”

Bennett is single and child-free, which also keeps his daily costs down.

He feels so passionate about Medellín that he founded a tourist company, The Paisa Plan, to help people plan their visits to Colombia and the city. However, Bennett declined to share what his company books in revenue.

He also volunteers his marketing strategy services for the Medellín Philharmonic Orchestra.

“It reflects my love, respect, and appreciation for my adopted home, and aims to help visitors really discover the magic of Medellín,” he said.

Jason Bennett said his family has enjoyed visiting him in Medellín, Colombia.

He said he is still smart about savings, despite having a lower cost of living.

Six years into his life in Medellín, Bennett said he has a better work-life balance than he ever experienced in San Francisco. Additionally, he said the city is full of energy.

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