Breaking Down and Breaking Through in Latin America

Jericó, Colombia

Latin America has played an important role in my adult life. In this essay, I share stories from Central and South America that have shaped my perspectives and worldview.

My intention with this essay is to share the highs and the lows of my journeys; the joyful moments as well as the downright frightening. I also recognize that many people don’t get to travel as much as I do, and I am grateful for the opportunities that I’ve had.

Costa Rica

Five years ago, I quit my job at a commercial bank in dark, chilly Buffalo, New York, and flew to Costa Rica to spend a summer studying coffee. I had been planning this for months; when the trip finally came around, I was jumping for joy, in light of my newfound freedom from corporate drudgery and seasonal affective disorder. It was time for some sun.

Costa Rica is a paradise. The tropical jungles, black sandy beaches, and hidden waterfalls are stunning. And right from the beginning, I had some of the most liberating and free-spirited adventures of my life. ATV rides through misty hills; hikes accompanied by colorful parrots; monsoon-like thunderstorms; nights out at dance bars with chain-smoking Europeans (all of them had the same explanation: “I only smoke on vacation because I know my friends will be smoking”); shenanigans with the bizarre characters from the hostel; and so on.

Photo Credit: Culture Trip

When I made it to the coffee plantations, built on volcanic soil in mountainous terrain, I told myself that I had finally arrived. Finally found my bliss. The anxieties and stresses of corporate life were behind me.

Photo Credit: Tico Times

Yet for all of the thrills, the summer quickly ended in failure. I arrived in Costa Rica without a return ticket, planning to spend the entire summer, and beyond, there. But less than three weeks after my arrival date, I was on a plane headed back to the United States.

I was seeking an internship or a working arrangement at a coffee plantation, and I struggled to find an opportunity. I barely spoke Spanish at the time and had little ability to communicate. I made the mistake of spending a week in San José, the capital city — a gritty urban jungle filled with concrete, traffic, and crime.

But above all, it was the fear. Four or five days into the trip, I started to feel overwhelming anxiety that limited my ability to enjoy my tropical surroundings. I felt pressure to figure my summer out and had no clear direction forward. I would travel to a new village, make a bunch of friends at a hostel, and yet the next day they would leave, and I was once again completely alone.

Looking back with the benefit of hindsight, there were plenty of ways that I could have made this trip work. I was offered a part-time job at one of the hostels I stayed in, in exchange for free rent. I met different people who said they could connect me to coffee farms and plantations. I could have gone to Spanish school. And so on.

But I can see all those things from my 28-year-old perspective. At 23, I was too shaken up to make it work. I could have stayed, but I was so unhappy that there was no point. And so I returned to the States to figure out what to do with my life.

It has taken me a long time to process this period of my life. I was thoroughly embarrassed by my failure. I had spent six months telling everyone I knew of my big plans; it was painful to see and feel this derail so quickly.

And for the poisonous icing on the cake, I ended up taking another corporate job that was even worse than the one before.

And as I’ve made sense of the whole thing, this failed journey wasn’t so much about coffee or Spanish or Costa Rica. It was much deeper than that, and I learned lessons that are true for many people in my generation.

The Lie

To properly frame how and why I ended up on this journey in the first place, it’s crucial to go a year back, to my college graduation in 2013.

I graduated from the University of Maryland, and I was optimistic, to say the least. I couldn’t wait to start working. I was a finance major, and I believed that my work at the bank would be filled with action-packed strategy, deal flow, and investment decisions. I was ready for a period of rapid learning and challenging problems. I was prepared to go out into the world and become part of the global economy. And banking seemed like the path forward.

How naive I was. Of course, I had zero perspective at 22.

But it’s important to note that my undergraduate business school classmates and I were sold a lie. By job recruiters, by professors, by University administrators.

Here is how that lie goes: the corporate world is an excellent place for you to gain experience, develop a skill set, and make connections and money. You will learn more than you’ve ever learned before. You will have to work very hard, and it may require long hours, but you will be challenged in critical ways. And who knows, maybe after a few years you’ll be able to start a business, work for a nonprofit, use your skills to make the world a better place. Repeat after me, corporations are an excellent place to start your career.

Inundated by this hypnotic propaganda throughout my four years in University, I bought into this lie 100%. And so did all of my friends. I told my parents that I was going to work for very long hours so I could especially get ahead.

Upon arriving at the bank, the lie unraveled quickly. My days were the opposite of exciting and challenging, characterized by sitting in a chair, staring at spreadsheets for nine hours a day, filling out powerpoints, answering emails. Sometimes I didn’t have enough to do, so I printed off long-form New York Times magazine essays and read for hours. Occasionally, I would block off time on my calendar — pretending to have a meeting — and escape to read over the local library.

Even worse, my initial enthusiasm for work drew the resentment of disgruntled co-workers — sometimes they wouldn’t even acknowledge me in passing.

It was the very definition of soul-crushing. This is the period when I learned what panic attacks were.

I was profoundly aware that the entire world was moving forward without me. Technology was improving exponentially, climate change was advancing, economic volatility was surging. And me? I was stuck in a cubicle, wasting my life.

And so, within two months of arriving, I was already planning an exit. This was not a place for me to be.

It wasn’t just me. ALL of my friends in corporate life were experiencing the same thing and hating it. I really didn’t know anyone my age who liked their job. And it took a toll on all of our mental health.

I discovered The Four Hour Work Week by Tim Ferriss around this time, a book encouraging a different approach to careers. I learned that deferred freedom and joy — AKA working for forty years and then retiring — was a pointless waste of youth. I finally saw through corporate propaganda, workaholism, and general BS. And thus, I began to plot my escape.

I had recently become interested in specialty coffee, partly because caffeine was one of the few things getting me through the day at the bank. My intrinsic motivation disappeared, and so I needed caffeine to maintain my mood or get anything done.

And so I decided to combine this newfound coffee passion with experiential travel; maybe I would even build a career in coffee.

And I was off.

The problem was that when I got down to Costa Rica, I didn’t have anything to stand on. Throughout my life, a considerable part of my identity was built on my academic success and my professional future. Getting into college and getting a good job were the two pinnacles of success that I learned and prepared for from a very young age. I had a vision for my future.

And with that vision erased — no tests to study for, no job hierarchies to climb — I felt myself down in Costa Rica with not a clue of what I was doing. After the novelty of vacation wore off, I was utterly lost. Beaches and jungles can only distract for so long.

For some, that loss of identity might be liberating. For me, it was excruciating. I had no place to channel my ambition, and I felt like I was slowly going crazy in paradise.

This was, of course, the inner void. This was the space beyond the pride of good colleges, good test scores, and job titles. This was the space beyond my egoic titles and superficial metrics of success. It was wildly uncomfortable because I was so filled with ambiguity and uncertainty.

Extended solo travel has a way of triggering this, as I’ve learned. Many people go on vacation to all sorts of exotic destinations, but they don’t leave their titles behind them. They’ll be back in their comfort zone soon.

But when you truly leave your comfort zone, everything gets a lot more uncomfortable. You can’t rely on your typical cultural norms or friend circles. Your professional story fades away.

I wasn’t in Costa Rica for all that long, but it was long enough to deal with all of this directly. And when it activated, I felt like the anxiety would last forever, and I would never find myself again. Moreover, I felt like something was seriously wrong.


I moved back home to Connecticut, started hunting for jobs again, desperate to save my career; I was afraid that I was on the route to failure. I applied for corporate jobs in New York and DC, praying that I could get back into the workforce.

More importantly, I announced to my parents that I was going to therapy. My anxiety was terrible, and getting in the way of my core happiness.

This was the critical decision that got me back on my feet.

Many people hold a stigma towards therapy. I never really felt that way, because I was generally so interested in psychology and self-examination. But at the same time, I’d never gone before, aside from a single session in college.

I met once a week with a clinical psychologist. Our sessions mostly centered around redeveloping self-confidence and figuring out how to get a job. I got positive results within about ten sessions, which prompted a move to Arlington, Virginia, and the next step in my life.

Therapy is fascinating because it is such a profoundly layered relationship. On the surface, you are walking into an office and have a discussion about your problems, perhaps venting about a problematic relationship. But you are also exposing a level of vulnerability to an experienced professional who has an immense amount of insight on the mind; you’re not just venting, you’re actually showing parts of yourself that you think are weird and learning from the wisdom holder that you’re completely normal.

If therapy is working correctly, the psychologist shouldn’t just validate you; he/she should compassionately challenge you. You’re not there to maintain a static identity; you’re there to evolve, and evolution can only happen with accountability. Your projections need to unwind; psychological defenses identified; emotions processed and more. It’s not supposed to be an easy process, but it does work. It certainly worked for me.

Like many young people at 23, I lacked perspective. My psychologist did have perspective, and I slowly realized the following: I did not know how to value my skills, traits, and abilities. I had a severely limited idea of what companies valued in an employee. And I did not understand that, despite my anxiety, I was actually in excellent mental health. I was more resilient than I thought.

And with all of that in hand, I was able to rebound and find myself back in the workforce. The next job was even worse, but I had made it through this chapter.


There is no doubt about it. I experienced an identity crisis through this transition, and it was incredibly challenging to go through. But it was a critical part of my development.

Twice, my expectations were hit with a hard dose of reality. My professional dreams were met with corporate slavery. Chasing my tropical caffeinated bliss turned into what felt like a breakdown.

With that step, it was undoubtedly the first step to my freedom.

Freedom in the confidence to check out of the rat race.

Freedom in the ability to be alone in a foreign country.

Freedom to experiment, freedom to fail.

Freedom to see myself clearly, without the academics or the job titles.

Freedom to confront and overcome the social stigma of unemployment. (Unemployment should be called freedom).

Freedom to step out of my own head and gain a better perspective from an expert.

Freedom to pursue a passion, even if, in the end, I wasn’t so passionate about this one.

Even though I failed miserably, I now had an operating template. I knew I could do this again. I knew I could survive.

Buenos Aires

In the summer of 2015, My good friend Bobby and I visited my cousin Danielle in Buenos Aires, who was doing a summer at an Argentinian hospital through her medical school.

Photo Credit: Americas Quarterly

Buenos Aires has a European charm with vibrant Latin flair. People are warm, passionate, stylish, expressive. There are pizza and pasta restaurants on every corner. The famous steak is omnipresent, and the red wine flows like water. The downtown is filled with architecture that feels more like Paris than South America.

Photo Credit: The Straits Times

Buenos Aires and Argentina also have dark sides. The economy has had significant problems over the past decade. Inflation and loose monetary policy lead to major jumps in prices, creating severe living conditions for the poor. Predatory hedge funds financed the country at exorbitant rates, creating a debt trap for the country. Cristina Kirchner, the former President, was indicted for corruption and general incompetence (My Airbnb host told me that “Christina is the Devil”).

All of this means that Buenos Aires has gotten a lot more dangerous and crime-ridden over the years.

Bobby and I were staying at a hostel in Palermo, one of the wealthiest neighborhoods in the city. The owner of the hostel, an outgoing Porteña (resident of B.A.), told us that Palermo was completely safe, and we could walk around outside 24/7 with no problems.

One night, we went out to a club in the neighborhood. It was a fantastic experience — Argentinians know how to bring the party.

Around 2 am, late for us but early for Argentinians, we decided to walk home — our hostel was only a half mile away. We crossed the nearby railroad tracks and entered the dark Palermo streets.

We thought we knew where we were going, but suddenly we were lost. We checked the map and realized we needed to backtrack. We were the only ones walking in the poorly lit streets. We reoriented and started back in the direction of the hostel.

As we walked along, I started to hear quiet footsteps behind us. I immediately put my hand in my pockets, to make sure someone wasn’t going to run by and grab my wallet. Before I knew it, there were arms around my neck, and I couldn’t breathe. I shouted out, “take my wallet! Take my wallet!” and I could see that someone had grabbed Bobby as well. And then I was unconscious.

And then I was right back. It sort of felt like waking up from a bad dream, except immediately discovering that the bad dream is real life. My iPhone and wallet were gone — only the hostel key and city map remained in my pocket. But I got up and was 100% fine, not even a scratch. Bobby was lying face down, unconscious right down next to me, and it looked like he had hit his face. Instinctively and immediately, I saw he was breathing and knew he was okay. I ran and shouted for help and found some people right away. The police showed up immediately.

I was in a state of shock, but I needed to handle the situation, so I explained what happened. Bobby was up but entirely out of it. They told us they could file a police report, but it probably wouldn’t make a difference, so the police and the other people offered to walk us back. In a moment of absurdity, one of the Argentinian men told me that he needed to explain to his wife why he was showing up late, so he took a selfie with me.


We got back to the hostel and started to process the situation. The next morning, Bobby needed to go to the private hospital to get stitches. We realized that our vacation was over, even if we were still in the country for a few more days.

The weird thing was, I started to feel a strange self-assuredness in the period following this experience. I knew this was a dangerous experience to go through, but at the same time, I learned that I was emotionally and physically resilient. I also learned that there was no point in being afraid. Just don’t do dumb things — i.e., walk around in Latin American cities in the middle of the night — and you just don’t need to worry.

I learned my lesson.

Don’t get me wrong — there was still trauma associated with this experience. It took me a long time to release this.

I think Bobby and I both realized that we were a lot tougher than we thought. Neither of us wanted to go through this type of experience, and I hope it never happens again. But we learned lessons that you can’t really learn from a book.

Sometimes the most vibrant of places have shadows that will bite you if you aren’t careful.

I still loved the Argentinian culture and would go back again.


On my first weekend in Mexico City, I hopped into an Uber and drove to one of the wealthiest neighborhoods in the city, where an acquaintance had invited me to a get-together. I expected to find oversized mansions and sweeping views of the city; instead, I found a gated community filled with concrete bunkers.

I walked up to the address I was given, where a guard with a giant dog was sitting behind a gated window. Video cameras peered ominously down at me.

I told the guard that I was a friend of Octavio’s. He shook his head, said he didn’t know who that was. Gulp. Did I get this address right?

For a moment, I looked around and observed my surroundings. What the heck was this place? Why did these houses look more like military grade installations than residences?

And then I remembered, I’m not in the United States anymore. It can be dangerous to be rich in Mexico. This country used to have severe issues with kidnappings. And the people living in this neighborhood clearly weren’t willing to take risks with their safety.

In any event, Octavio and his friends showed up in a car, and we all went into the house, owned by the relative of another friend. Behind the cement facade was a beautiful home with a spacious backyard. Military security on the outside; domestic tranquility on the inside. Fifteen or so people showed up for the small party; I was the only American there.

And so when they broke the karaoke machine out, I was more than happy to be the token gringo at the party who gets up and sings. Turns out that a willingness to make yourself look ridiculous is a fast way to make friends in Mexico.

And I spent the remaining ten days in Mexico hanging out with this group of people.

Inaugural Taco Stand Visit

I’ve been back to Mexico plenty of times since, and I’m continuously fascinated by the country. On the one hand, it can be brutally violent and filled with regions that are mostly no-go for tourists; on the other hand, it is a nation rich with food, culture, beaches, jungles, indigenous tribes, and so much more.

It is choked by bureaucracy and corruption; on the other hand, Mexico City is the largest megacity in the Western Hemisphere and is a critically important trade zone.

Nevado De Toluca

In some sense, I keep returning to Mexico because it feels like the best-kept travel secret lying right under America’s doorstep. I’m specifically not talking about tourist areas like Cancun or Cabo; I’m talking about the Mountains of Oaxaca, filled with pristine forests and landscapes that feel straight out of a MacBook Pro background; I’m talking about the bustling city of Guanajuato, a college town filled with pastel facades and oversized churches; I’m talking about Nevado de Toluca, a hikable volcano only two hours outside of Mexico City; I’m talking about the city of Puebla, filled with classic Mexican streets and home of the famous mole dish.

San Jose del Pacifico

Americans are so frightened by the headlines that display Mexico as a warzone that they end up missing out on these types of destinations, which are only a small sample of the destinations that the country has to offer. Is Mexico dangerous? Of course, it is — in certain places. But it is a huge country, and it isn’t that hard to find places that are much safer for Americans to travel to.

For all of Mexico’s political problems, it does get a lot of things right. I would start with culture; Mexico tends to be far more communal than the United States.

Adventures in the streets of Oaxaca

The U.S. tends to place the individual above all else — our values center around individual accomplishment, individual growth, personal meaning. This has its benefits, of course — it has sparked the rise of incredible economic and technological successes, as well as relative tolerance of divergent or contrarian opinions. However, we’ve seen a depletion of the American cultural fabric, starting with family and religious life, and extending into the realm of our digital experiences. Thus, we see a rise in loneliness, alienation, and shame.

Octavio smashing a coconut

I learned of the deep communalism of Mexico through Octavio and his group of friends, when they expressed during the mansion bunker party that they would hang out with me every single day for the rest of my time in Mexico. They literally took shifts to ensure that I was always with someone. Remember, they weren’t close friends before I arrived in Mexico — I had only met Octavio once before. Of course, they were by the end.

In my experience, that’s just not a thing in the United States. Even when close friends visit, we might hang out with them for a couple of days. We’re too busy; we’re too overcommitted; we’re too overwhelmed. The thought of giving someone that much time is out of the question. (Or maybe my karaoke was just excellent).

San Miguel de Allende

And that’s fine, but at what cost? Is it possible to build relationships when you aren’t willing to commit significant amounts of time to others? Are you able to be happy if you’re so wrapped up with your life that you can’t go out of your way for someone else?

That’s the simple theme that Mexico (and Latin American culture) seems to get right. It’s not as developed as the United States, but people seem happier. Families are more connected. There is human decency that seems consistently present, even as society has its violent shadows and scary facades.

And perhaps Mexico will be the saving grace of American culture. As much as our neurotic-in-chief tries to fight a trade war with our southern neighbor, we have to acknowledge that our country is filled with Mexicans — California is more Mexican than Caucasian — and they are here to stay. In the same way that Black culture is profoundly integrated into the mainstream popular thought, Latino life will continue to exert an influence on the direction of our country. Latino families have high birth rates, and as they say, demographics are destiny.

And perhaps that will properly counterbalance the unchecked individualism in our country. We have a lot to learn.

If you want to understand the future of the West, Mexico, is a good place to start.

And that is why I am learning Spanish — more on that in the next section.


I’ve never been to Venezuela, and it is not a safe place to travel right now. But it has nonetheless played an essential role in my path.

At a certain point in my Latin America journey, I decided that I was tired of not speaking Spanish. Playing the whole lost in translation game/communicating through google translate/apologizing that you only speak “un pocito” can get really old after a while.

I intended to keep going back to Latin America, not to mention that California is packed with Latinos. So I decided to commit to learning Spanish.

I studied French in middle school, high school, and the beginning of college. These years gave me proficiency in grammar and extensive vocabulary. But the lack of communication with native speakers prevented me from getting anywhere. I was never fluent in French and strongly desired to learn another language.

Before I ever traveled to Latin America, I completed Duolingo Spanish, and it got me nowhere. I learned some words, some verb conjugations, but in reality, it is not possible to learn a language through a non-human software program. There are no shortcuts. The only way is through regularly speaking and practicing with a fluent Spanish speaker.

The ideal is Spanish immersion. But the next best thing is working with a tutor. And so I searched for a Spanish teacher online through the platform

I was looking for something cheap and effective. And as I learned, Venezuela had the most affordable Spanish teachers by far.

Venezuela has been engulfed in an inflation crisis over the past years, due to economic mismanagement by the Maduro regime. A country that used to be one of the wealthiest places in South America now struggles with mass starvation.

But they still have internet, and so I was able to connect with Gabrielys Meza, a young Spanish teacher living in Maracaibo, a city west of Caracas. She only spoke Spanish, and we started at the very basics; learning the numbers and the alphabet (like I said — Duolingo got me nowhere).

Caracas. Photo Credit: Wikipedia

I was dead set on achieving fluency, and so at the beginning, I studied with her an hour a day for seven days a week. Through the process, I built the foundations of Spanish fluency, but I also learned about life on the ground in Venezuela, unfiltered through media headlines. I learned of the struggles in her community, but I also learned of the normalcy that people struggled to maintain. She spoke to me about the culture in the streets, the Venezuelan holidays and festivals, her family relationships, the differences between Catholicism and Protestantism in Latin America, and far more.

And my Spanish abilities took off.

I went from struggling to put basic sentences together to having complex discussions about politics and economics. I went from conscious conjugation to unconscious fluency in approximately 18 months. Again, this was thanks to working with an excellent teacher on a frequent basis.

There is something particularly strange about spending so much time with another person even though you have never met in person. I’m still studying with Gabrielys, and she is a close friend, almost like a family member. This is what happens when you spend this much time speaking together about the mundane and exciting facts of life.

It was also thrilling to watch my learning curve — to be able to travel in Latin America, and really be able to get around by myself, communicate with the locals. Don’t get me wrong — there are still times where someone speaks to me rapidly in heavily accented Spanish, and I don’t have the faintest clue of what they are saying. But the moments where I feel like an idiot speaking Spanish (an inherent part of the language learning process) are steadily decreasing.

I will continue to pursue my studies in Spanish for several reasons. First, the United States is increasingly Latino; Latinos outnumber Caucasians in California. I hear Spanish being spoken everywhere I go in San Francisco. And while Mexican immigrants should certainly learn to speak English, I firmly believe that Americans should learn to speak Spanish. It is a matter of utility, and it is a matter of respect. The demographic future of our country is Latin, and we need to integrate that.

Second, personal growth. Language learning opens up extraordinary doors in your mind. Perception of reality is heavily influenced by the words and language you use to describe it; when you become fluent in another language, you gain a new perspective on how to look at the world. In my experience, describing the events of life through the Spanish feels more emotional and yet relaxed. (“me duele la espalda” vs. “my back hurts”). That’s subjective, of course, but then again, there is a clear link between language structure and emotive experience.

Third, identity. In my experience, people tend to get consumed by their career, social, and romantic, and family activities, to the extent that they begin to define themselves exclusively by those things (i.e., people who work in a job they hate and complain about how much they want to get out, going to a bar and keep talking about work after they’ve left the office — it defines who they are). It is imperative to diversify and expand your identity so that you aren’t boxed into a limited sense of self. In my experience, language learning creates that expansion.

And so on.

The other benefit of my Spanish lessons was the opportunity to learn about a conflict zone through the eyes of a local, and support someone who is struggling to feed her family. We are so immersed in the internet on a day to day basis that we forget how utterly powerful it is. Video-chatting with Gabrielys gave me a brand new way to understand civil unrest.

If you’re to believe the headlines, all of Venezuela is in a constant state of violence. We see the videos of protests in Caracas, of people marching through the streets, of tear gas, and more. This is all real, but it’s necessary to realize that political violence is minimal relative in proportion to the broader country. The deeper problems that people in Venezuela deal with are more like a constant grind: exorbitant food prices, inability to access basic medicine and healthcare, power and water outages, mass immigration. I used to sardonically joke that if the video chat connection dropped, I didn’t know whether it was my wifi or the Venezuelan power grid.

In all seriousness, power connection has been the biggest challenge in continuing the classes. At one point, I had to loan Gabrielys a fair amount of money to upgrade her internet connection to be able to continue lessons without power. It was the least I could do for someone utterly dependent on the internet to make money.

But at the same time, Gabrielys does earn money in dollars, meaning that she doesn’t feel the full effects of inflation from the Venezuelan Bolívar. Though most people in Venezuela can’t make dollars on the internet, it is still extraordinary that this is an option at all. In many instances, it is the only reason why people can continue to live there.

At a more ideological level, it’s become clear to me through my conversations with Gabrielys that socialism and economic protectionism — leftist politics as they are practiced in Latin America — simply don’t work.

Nicolas Maduro, President. Photo Credit: Fortune

I empathize with the idealism of leftist activists, who resent the historic military interference and espionage of the US military in Latin America. But I do not empathize with their tendency to overlook the terrible political and economic situations that leftist governments manifest in this region, nor the continued support of U.S. leftists for these governments when people on the ground are starving. As a recent example, Dr. Jill Stein, 2016 Green Party Presidential candidate angrily defended the Maduro regime on Twitter and accused the US government of causing people to suffer by waging economic warfare against Venezuela, ignoring the fact that Maduro — backed by the Russian government — has sociopathically blocked food, water, and medical supplies from entering the country.

We’ve seen leftist politics play out in Latin America before. Argentina’s massive currency issues (courtesy of the Kirchners), the collapse of the Chilean economy in the 1970s, the Nicaraguan government firing on student protesters in 2018–9 (linked to economic issues), not to mention the previous crises in Venezuela. At a certain point, it’s time to stop saying that leftist governments haven’t been given a fair chance, and it’s time to stop blaming these inevitable problems on capitalism. Centralized economies don’t work, nationalization of private industry repels foreign capital, excess printing of currency erodes spending power, and trade wars hurt exports.

And at the end of the day, there are human lives at stake.

More effective and empathetic activism in Latin America would stop fighting social/capitalist proxy battles and focus on improving the lives of people on the ground. The good news is, it is easier than ever to support local Venezuelans. As the digital economy expands around the globe, one of the rays of hope is that people in difficult political situations will have more opportunities than ever to earn money from abroad.

These classes have opened a fascinating chapter in my Latin America journey. Unfortunately, I can’t actually visit Venezuela because of the security situation, though I stayed close to the border when I traveled in Colombia. I also occasionally visit Venezuela in my dreams.

Espero que yo puedo visitarlo en el futuro/ I hope I can visit there in the future.


Last year (2018) began on a high note. I was running a startup consultancy and was managing my most lucrative contract to date, a Google Adwords campaign for a funded tech startup. And yet only days after the year started, things took a volatile turn (as startups tend to go) and the client fired us.

What a blessing that was. I declared that I would never run a paid digital advertising campaign again. And for the first time in eighteen months, I found myself without any clients to directly manage.

And so within weeks, I booked a flight to Colombia and planned to stay there for six weeks. I needed a break — dealing with clients is stressful and burns you out. I was tired of the roller coaster.

I also had been studying Spanish intensively for three months at this point and was ready to put my skills into action. I wanted to spend a significant chunk of time in a Spanish-speaking country.

Why Colombia? Well, this answer might seem ridiculous, but it’s the truth. I was watching Narcos, the addictive Netflix series about Pablo Escobar’s drug trafficking empire, and I was inspired to visit.

Yet I wasn’t engaging in narco-tourism, a trend where American and European tourists cynically stake out the old stomping grounds of a man who terrorized the country for years. Instead, as I watched the show, I was struck by the landscapes, the culture, the incredible beauty of the countryside. I could genuinely feel the magical realism through the television. And once I started having dreams about Colombia, I knew that I needed to visit.

And thus I found myself down in Medellín.


This was a Karmic journey, of sorts. Though I had returned to Latin America several times since my failed Costa Rica experience, I hadn’t completed an extended solo trip. And I needed to prove to myself that I could do this — that I could hop on a plane, and venture around a foreign country by myself, without freaking out, without losing my sense of direction, without needing to go back to the United States and figuring out my career direction. Colombia was about sitting with the ambiguity, navigating but not rushing a life transition, following my intuition and letting the flow take me wherever it went.

Banana Farm outside of Manizales

And so my journey took me all over the country, from the bustling metropolises of Medellín and Bogotá, to lush banana farms in the coffee triangle, from the violent and dangerous city of Cali (the Salsa dancing Capital of the World), to the calm and tranquil university center of Bucaramanga.

The highlight of my experience was a trip to Chocó, a region on the Western coast of Colombia, so radically underdeveloped that it was impossible to drive there and I had to take a plane. Chocó was previously controlled by the FARC, Colombian rebels who hid out in the jungle, waging a brutal guerilla war against the government for years. It has only recently become a safe place to visit, and even still, the region is filled with drug traffickers, moving their product towards Central America. Chocó is one of the most biodiverse areas on the planet. It is so undeveloped that the local towns lack municipal trash collection systems.

Photo Credit:

Clearly, this was a bit off the beaten path. But that was precisely the type of experience I was seeking out, and intuition brought me in this direction. And the next thing I knew, my plane landed on a runway carved out of the jungle, and soldiers from the Colombian military checked my bag. And I then I hopped on some sort of a golf cart/buggy, which drove me to a small hostel directly on the sparkling beach.

There is a certain feeling of being far away from society that can’t really be expressed until you actually go there. It is a mix of liberation and fear, the natural sensory awareness that you have arrived at the frontier. And what I found at the frontier gave me new ideas about humanity, technology, and the natural world.

If you dropped out of a plane and landed into Chocó without any knowledge of your location, you’d be forgiven for thinking you were in Africa. The local town is mostly populated by dark-skinned Afro-Colombian people, descendants of slaves who fled plantations and escaped to the coast. The people, though poor, were incredibly friendly and welcoming towards visitors.

Photocredit: Colombia Reports

The attraction of Chocó is its biodiversity and natural environment. Its beaches and jungles are untouched by development and are filled with crabs scuttling around. Towering palm trees overlook waterfalls and rivers flowing out into the ocean. Walk one mile in any direction, and you have a tropical paradise to yourself. It is extraordinary.

Parque Nacional Natural Utria. Photo Credit:

I joined tours to visit the local national parks, visited islands with azure blue water, canoed deep into the jungle, hiked through mangrove swamps (not minding the soldiers camped out in full military gear) and more.

Bahia Solano — Photocredit: Flickr

I strolled through the streets of the small town of Bahia Solano, watching the local children kick their soccer balls around, and attempted to speak Spanish with the heavily accented locals. I spent my few pesos on restaurants and tropical fruit, needing to be frugal as the town lacked an ATM machine. I slept in a hammock and listened to the rain pounding the sand, while I swatted mosquitoes by the dozen.

Several ideas occurred to me.

First, the environmental paradox. Chocó was the most remote place I had ever been, and the ubiquitous wildlife reflected this. The lack of development and human activity meant that species of all kind could thrive.

Yet pristine would not be the right word to describe it. All of the beaches I visited were dotted with plastic trash. This is due to the lack of a municipal trash management system, as well as a lack of awareness. Locals toss their plastic waste into the ocean.

This presents some challenging questions about environmental protection. First, is the obvious: Regions like Chocó need to be radically protected. Intrinsically, these zones are sacred and cannot afford to be lost. And the health of the biosphere as a whole is highly dependant on local wildlife protection.

Second is the corporate question. That plastic didn’t appear out of thin air. The local community was drinking Coca Cola, bottled water, and other typical plastic products (you could tell from the trash on the beach). And this raises the question — is this exploitation? If Coca Cola knows that it is selling its products where the plastic will end up in the ocean, is it ethical to sell it in the first place?

Free market proponents will say that this is the government’s job, not the corporations. But that is unacceptable. The Colombian government ignores Chocó (Coca Cola’s supply chain extends to plenty of relatively ungoverned states and regions) and plastic ends up on the beaches even if the companies claim it isn’t their responsibility to manage the full lifecycle of their materials. This outcome I witnessed is frankly disgusting, and something needs to change.

I am explicitly not arguing for more regulation, which probably wouldn’t be effective in a place like Choco anyways. I am demanding authentic corporate responsibility, where multinational corporations take ownership of the externalities, should we say more directly, consequences of their business models. This would represent real leadership and the changes we need to see in the world.

Third, development. The towns I walked through were incredibly poor; this region clearly needs a lot more local services and education.

What would progress look like in this place? Would things really be better if Chocó developed economically and subsequently destroyed its wildlife? Is the status quo of poverty acceptable? Would government attention and intervention benefit or devastate this region?

I am left with more questions than answers.

Another observation. What immediately struck me was how ubiquitous smartphone use and social media were among the locals. I had read online in advance that Chocó didn’t have much internet, and I shouldn’t expect to be able to communicate with the outside world. To the contrary, as soon as I showed up to the hostel dining room, the chef’s young daughter was sitting and watching an endless chain of cartoon Youtube videos. It was the same everywhere I went.

It was striking to me that this community, lacking even the very basics of municipal systems, has continuous access to high-speed digital technology. On the one hand, this kind of access to information has powerful implications for education. However, if fake news is a problem in educated areas, I can’t even imagine how bad the locals here could be deceived by false or deceptive information.

At a more philosophical level, I suddenly understood the psychological truth of digital technologies; no matter how you frame them in a moral sense, their appeal is universal. Even (or perhaps especially?) communities that have been completely cut off from outside culture for their entire lives, impoverished and barely scraping by, find immediate addictive appeal in smartphone technology.

In any event, there are some very strange experiments running in the world right now, and I don’t think anyone knows how this will play out in a cultural trajectory. Will this mean the end of local customs in remote or underdeveloped communities? Will this enhance their education or just create endless loops of distraction?

In any event, continued digital access and use is unstoppable at this point; the best thing we can do is study, watch, and learn.

And then a personal reflection. One of the reasons I came to Chocó was that I was burned out by the tourist trail in Colombia. The beaten path may be safe, but it is also clogged with a lot of stuff that I’d rather not continue to experience. The uniqueness of the Chocó experience lit me up in many ways, and I’m setting an intention to go on more of these types of adventures.

Several weeks after Chocó, my journey is Colombia was complete and successful. This constituted a tremendous victory. Where I had failed in Costa Rica, I succeeded in Colombia. Older, wiser, and more adept in Spanish, I was able to dive into the local culture and grow in numerous ways.

Six weeks also gave me space to clear my head and think about what I really wanted to do in the world. I was tired of consulting and wanted to do something bigger for the world. I was ready to do something big for the world. Shortly after returning to San Francisco, I founded Aqueduct, a water technology company.

Closing the Loop

Latin America has been an education. Though it essentially is one singular geographic block with a shared language, it is a tapestry of different cultures, foods, traditions, landscapes, and so much more.

Jardin, Colombia

As I’ve argued in the previous essays, if India was the right of passage for counter-culture boomers in the 1960’s, Latin American (especially Peru), is the spiritual destination of truth seekers in the present. It holds badly-needed wisdom that is needed in order to course-correct pervasive cultural and emotional dysfunction in the United States. As Americans journey south of the border, we need to treat these countries with respect and integrity, and not use them as our dumping grounds.

I am incredibly grateful for what I’ve learned during these Latin American journeys and plan on revisiting many times. Pura Vida.

Co-founder, Streetlight.