Why this man swapped San Francisco for Colombia

After spending several years building a life he loved in San Francisco, Jason Bennett, originally from the Bay Area, had every intention of remaining in the Californian city for good.

The senior marketing executive, who previously worked for Gap Inc., says his main goal was “to continue climbing the corporate ladder” and he couldn’t really envision being anywhere else.

But in 2018, Bennett packed up and moved to the South American country of Colombia permanently after “falling hard” for Medellín, once one of the most notorious cities in the world.

He now works for himself, running two companies, from his “adopted home.”

“Life surprises you,” Bennett tells CNN Travel.

So how did he end up ditching the US and moving to a destination he hadn’t even visited until two years earlier?

Big decision

Bennett, who first moved to San Francisco in 2006, explains that he had begun to feel disconnected from his job, as well as the city, and questioned whether he really wanted to spend the rest of his life “in an office working for other people.”

“I wouldn’t quite call it an existential crisis, if you will, but I was getting a lot less fulfillment out of what was in my bank account,” he says.

“And I was getting very frustrated with San Francisco, and these things were not adding up anymore.”

After almost a decade in the city, Bennett, who says he’d been “saving religiously” for years, had been able to travel to far-flung destinations such as Lebanon, India, Estonia and Argentina to see music artists with his friends, and his perspective on life was shifting.

“I was feeling just optimism and positivity in the air in these cities, that I found, frankly, missing when I would go back,” he says.

“And it started to create that kind of trigger and thought in my mind, ‘Maybe there’s something else out there.”

Feeling disillusioned by the life he’d thought he wanted, Bennett resigned from his job and started up his own marketing company, True Star Consulting, in 2015.

“You’ve got to jump sometime in life to know if you can do it or not,” he says.

Bennett also decided to take a break from the US and spend a few months traveling the world, while working remotely.

Later that year, he visited Lisbon, Portugal, before moving on to Cartagena, Colombia.

“I knew after a week that I would never return to my old life,” he admits. “But I didn’t think I would ever permanently settle somewhere else.”

While he wasn’t that enthralled by Cartagena, Bennett felt something change inside him in April 2016 when he arrived in Medellín, nicknamed the City of the Eternal Spring.

“There was an energy I had never felt before,” he says. “The food and weather were awesome, the metro astoundingly pristine.”

He planned another visit, and found that he experienced the same surge of energy when he returned in 2018.

“But above all, I was especially taken and inspired by the happy and friendly people, who I found completely remarkable given what they had gone through.”

Leaving Medellín to continue his travels, Bennett was hit with an overwhelming sense of sadness and longing.

“It was then that I started to say, ‘Do you really need to leave?’” Bennett says. At the same time, he realized that he was mostly returning to San Francisco because he felt that was what was expected of him.

“Well I don’t want to do that anymore,” he thought to himself. “And my happiness levels are off the charts when I’m in Medellín.”

Bennett ultimately decided to “cut ties” with his life in San Francisco, and went on to sell his one-bedroom apartment there, and buy a two-bedroom property in the neighborhood of Castropol in Medellín’s El Poblado district.

“As luck, or karma, would have it, I accepted an offer on my San Francisco apartment the very same weekend my offer was accepted on my Medellín apartment,” he says, before explaining that he subsequently had “a 45-day clock to unwind” his life in the US.

According to Bennett, his new apartment was “roughly 80% cheaper per square foot” than his Californian abode at that time.

After selling his furniture, shipping over some of his possessions to Colombia via Miami and filling two suitcases with clothes, some artifacts and his beloved coffee maker, Bennett set off to begin his new life in January 2018.

“I really remember turning and locking that door,” he recalls. “And emotionally, I was done. There was no lingering. Like, ‘Is this the right thing to do?’”

Adopted home

Bennett says he immediately felt at home in Medellín, recalling how the “warmth and kindness” of its people pulled him in.

“I always have felt a draw to the Colombian people,” he says. “And specifically those from Medellín. For anyone who’s not been here, the warmth and kindness is off the charts.”

Bennett says he was particularly impressed by the lengths locals were prepared to go to help others.

“It’s that much more remarkable given that this city, 20 or 30 years ago, was so feared by so many,” he says, reflecting on Medellín’s controversial past.

The city, the second largest in Colombia, was once home to the Medellín Cartel which, led by drug lord Pablo Escobar, terrorized the country for decades. As a result, Medellín was synonymous with cocaine and murder up until the early 2000s.

“That they have chosen to create a culture and a community of love, respect and connectivity, rather than one of hate, divisiveness and anger,” adds Bennett.

Although Colombia has a long association with drugs and gangs, the country’s murder rate dropped by 82% from 1993 to 2018, and crime rates in Medellín have lowered significantly over the years.

“I feel safer here than they do in America, without question,” says Bennett.

According to Bennett, one of the best things about living in Medellín is the quality of life.

“The drinking water is phenomenal,” he says. “We have our own reservoir system… The food is incredible. We can grow anything all the time. The fresh fruits. It’s such a healthy lifestyle.

“The coffee level, of course, is out of control. And the amount of parks, I can take you to 10 different parks that I love.”

He’s also full of praise for the country’s health care system – the World Health Organization ranked Colombia at number 22 in an analysis of 191 countries – describing it as “phenomenal.”

“Healthcare is a constitutional right here,” he says. “And there is a public system that is available to everyone.”

Bennett, who pays around $2,000 a year for a private medical plan, says he’s been able to build a personal relationship with his doctors in Medellín.

“I have had access to the best medicalists that I have ever had in my entire life,” he says.

“Not that my doctors in the United States were not good, but (here) I sit with my doctor for an hour. We talk about life.

“You feel like you’re just a number and you’re rushed in and out in the United States.”

Bennett is also a big fan of the city’s metro system, a network of trains, cable cars, trams and buses, which first opened in 1995 and is now one of the most successful in the world.

“They started building this network during the worst of the violence, and it came to be seen as a symbol of hope for the city,” he says.

“So it is the cleanest, most respected metro that you will ever come across in your life, except for maybe Japan.”

Cultural differences

Although he clearly loves being in Medellín, there are some aspects of life in the US that he misses.

For Bennett, the “level of directness” of the people is probably top of the list.

“The (Colombian) culture is so kind, they don’t really like to say, ‘No,’” he says. “So you ask questions, and you often don’t get a straight answer.

“You’re like, ‘Come on. You can just tell me how it is. I’m not going to get mad at you.’”

He goes on to explain that he finds Colombians to be more relaxed in general, and “people don’t really act with the sense of urgency that you might get in America.

“I do miss that,” he admits. “But on the whole, I’m around much happier people. So I feel that it’s a worthy trade off.”

Bennett notes that it can take a little while for newcomers to figure out how to get important services like bank accounts and energy services set up in the country.

“It takes time,” he notes. “It’s not as quick as in America. It’s not as quick as what you might be used to. There are steps you need to take, and you have to be persistent.”

When it comes to affordability, while Bennett points out that “inflation has raised prices on quite a few things compared to what they once were,” he still finds Medellín to be incredibly good value.

“Excellent meals can be had for under $10, Uber is not expensive, and the world’s best coffee is less than $2 a cup,” he adds.

After six years, Bennett is fully immersed in the Medellín experience and the city feels very much like home.

He’s not quite fluent in Spanish yet, but after studying the language for five years, Bennett says his confidence is growing and he’s able to hold conversations reasonably comfortably.

“It’s my duty as a guest to learn the language,” he says. “That’s the thing that kind of kills me about some expats, is that they don’t learn any Spanish.”

Although he does have some friends in the city who are fellow Americans, Bennett says he tries to avoid hanging with “expat groups,” preferring to spend time with locals.

In 2022, Bennett launched a tourism company, The Vegan Paisa, now know as The Paisa Plan, with the aim of helping others discover the “magic of Medellín.”

“The name was inspired by the moniker (Paisa) for those born in Medellín,” he adds.

Bennett currently has a residency visa, which he renews every five years, but plans to apply for Colombian citizenship in the future.

“I want to be here for the rest of my life. It’s a reflection of who I am now,” he says. “The values that Medellin stands for are the same values that I stand for.”

However, he goes on to stress that he has no plans to renounce his US citizenship.

“I happily pay taxes to the US State government,” he says. “And I don’t ever want to come across as like I’m shading San Francisco or the United States in general.

“But I do sense a profound energy shift when I go back to visit my family and I look at a country with abundance and with resources that are the dream of so many.

“And (think) how did it devolve into constant fighting, election conspiracies, healthcare not being a right, women’s rights being taken away, guns everywhere?

“They just broke every contract that you as a citizen expect of your country.”

Bennett last returned to the US this May. Both of his parents have traveled over to Colombia to visit him, along with his sister Jen, over the past few years.

“One of the nicest things my mom said was how she felt safe in crowds for the first time in long while,” says Bennett.

While he hasn’t been able to explore much of the rest of the country, aside from visits to Bogota, Cali and Cartagena, he hopes to rectify this soon.

“I have a lot more of the country that I want to see, for sure,” he adds, admitting that he misses Colombia whenever he travels elsewhere.

Bennett acknowledges that many of the decisions that he’s made with regards to his career and the destination he lives in have been easier due to the fact that he’s single with no dependents.

“I’ve never wanted to get married,” he says. “I don’t have kids. My time is my time. I realize that that is not the reality for a lot of people.

“I’ve crafted my life that way… I decided that I wanted to have that freedom of time and location and all of that.”

He advises those who are thinking of making a similar move to spend some time working towards it and coming up with a strategy.

“You’ve got to have a long term plan,” he says.

Since choosing to relocate to Colombia, Bennett has noticed a considerable change in his overall wellbeing and says he couldn’t be happier with how things have turned out.

“As I’ve gone into my 40s, it’s lowered my stress levels immensely,” says Bennett.

“I can just get around that energy and vibe and kind of soak it in. It puts me in much better health, physically and mentally, as I continue to call Medellín home.”