So This is Goodbye


I’m writing to let you know that this is my last week living in Chile. These past nine months have been transformative. Moving here was not the easiest thing I’ve ever done, but I’m so glad I did it. Now I must be going.

You and I got off to a bad start. From the beginning, there were problems. There was the visa and the Civil Registry. I waited there for days only for you to spell my name wrong, and then I had to do it all over again. Endless forms and documents and pointless bureaucracy.

My first roommates were horrible human beings. My first employer was seedy and unfair. My first experience dating a Chilean girl was, well, frightening. I suppose my lack of Spanish didn’t help any of this.

I couldn’t find anything good to eat here. You left me disappointed so many times. With your hotdogs and your piles of flavorless meat and bread. Why does everything lack flavor? What’s the deal with all the mayonnaise?

In October, a waiter dropped a completo on my leg. I watched it tumble midair, somersault twice, and then land, face down, on my new pants. I’ve never seen so much mayonnaise on one person’s body. It took about a hundred napkins and an awkward explanation at the drycleaners to get the milky stain out.

Two lines for everything: one to pay, another to get your food. Employees standing around doing nothing, handing out receipts and then stamping them. They stamped my receipt for a turkey sandwich with a sense of importance as though it were a travel document, and they were a border official. The unprecedented inefficiency ate away at my gringo core.

After just a few months, I was ready to give up and come home. But I reasoned that I needed to “Give it more time.” How much can you really know about a place after just three months? I mean really?

I changed apartments and got rid of the roommates. I quit my job and got a new one. I continued to try to make friends, and did.

I traveled around Chile. I went hiking in the Andes. I learned how to surf at Pichilemu. I watched the sunset in the desert at San Pedro de Atacama. I stared into the crater of a volcano in Pucón. I had a zen-like experience in the Elqui Valley. I felt the ground move beneath my feet in Santiago–my first temblors. I started thinking about the Earth differently–as being alive.

I went off on weekend adventures and marveled at the variety of landscapes encased in this tiny strip of land. Still at the end of each trip, I looked forward to coming back to Santiago less and less.

My restlessness became apparent. When I got here, Chileans would ask me, “Why Chile?” Now they were asking me, “So when are you leaving?” I realized what they already seemed to know–I no longer wanted to be here.

I never intended to stay forever. Really I’m not sure how long I thought this would last. I bought a one-way ticket and sold all my furniture in New York. I told people I’d spend “three or four months” here. We both knew that it’d be longer, as long as I didn’t hate it.

After nine months, I’m calling it quits. On Friday, I fly to Bogotá and from there I’ll go to Lima. I’ll spend some time traveling and after that, I’ll go home for a while.

When I look back on my time in Chile, I cannot deny all the amazing things about this country. One thing in particular, the people. Since I got here, they’ve treated me as though I were one of them. I have been moved by their hospitality.

In November, I met a young married couple at a language exchange, an event where you can practice Spanish or English over beers. Ironically they had just returned from New York where they had lived for a year. Separated by continents and sheer distance our whole lives, we were suddenly and inexplicably linked.

What began as many friendships between gringos and Chileans do–as a way to help one another learn our respective languages–quickly grew into something much more. They invited me into their home on Christmas and again on New Years. They helped me and provided guidance in every way that you can. They reminded me that family is important. Despite everything, they make it difficult to leave.

Santiago is not known for nightlife or cuisine. I could have stayed up all night in Rio de Janeiro and reveled in gastronomic genius in Lima. Yet somehow I think you were just what I needed. I have no regrets about coming here. Thank you for everything. I am so happy with the friendships I’ve made and the experience I’ve had.

I’ll see you again soon. For now, so long, chau chau.


Calle San Isidro

The first place I took my mother when she visited Santiago was La Vega, an immense, chaotic outdoor vegetable market. Two days later we went to Bio Bio, an even larger, more cluttered flea market.

My friends were horrified.

“You took her to Bio Bio?! Why?!”

In a city that underwhelms, Bio Bio and La Vega are bastions of hope. I go often, usually not to buy things, but so I can feel like I’m in Latin America. If I have a visitor, I insist on taking them to the street markets, ferias, as they are known.

In February I moved downtown to Calle San Isidro. I fell in love the first time I walked down my street. When I saw the crowds and the street vendors. It was a burst of energy in a place where everyone seemed kind of sleepy.

On Calle San Isidro, there are scarves for sale and women swarming. Tables full of pirated DVDs. There are people selling soy hamburgers, salad and sushi out of beach coolers. Women with makeshift shopping carts where they make orange juice; others equipped with deep friers, serving chicken and fries with ketchup.

Keep walking and there are guys selling toilet paper. Yes, toilet paper. They have household products, too, like Windex, toilet bowl cleaner and bleach. Right there on the street.

They come each afternoon and set up shop. Crowds gather, and by midnight everyone goes home. The next day they are back again.

Bio Bio, or Persa Bio Bio (its full name), is the Mecca for street vendors. Located in southern Santiago, just off Franklin Street, it’s massive and stretches for miles. Here you can find just about anything. When I say anything, I mean anything. If your phone gets stolen, Chileans will tell you to look for it at Bio Bio. Someone’s probably selling it there.

I took my mother on Sunday, the day the market swells to its maximum size. Within minutes, I sensed she was overwhelmed. So was I. In the meat section, we spotted severed pig heads for sale. Casually placed in the butcher’s case, next to the chicken breast and pork loin, their eyes looked back at us; they appeared to be smiling. Various body parts next to them, including hooves, ears and intestines. We both grimaced; she looked away and then laughed.

“I have to take a picture of this.” She winced.

The butcher walked over, smiled and shouted at us in indecipherable Chilean Spanish. All I could make out was “Tres Luca!”

We turned and kept walking towards produce. Heaps of carrots, cabbage, and strawberries; garbage strewn about the sticky ground. A woman hammered a machete into a giant pumpkin. Stray dogs roamed around us. Everyone shouted and pitched their products. “Una luca, tres por luca, luca, lukitaaa!”

(“Luca” is Chilean for one thousand pesos (about $2). Chileans like to add “ita” or “ito” to words wherever possible.)

My theory is that it’s impossible to see all of the Bio Bio market.  It’s like the universe, continually expanding, probable that no human will ever reach the end.

We had a vague idea about buying a map of Chile for our house (My mother’s idea). We looked around but not very purposefully. It’s hard to find anything specific there. Unless you know where things are (I don’t) you just go and walk around.

We walked down a street. No maps, but tables with old cameras, antique chairs, calculators, and books. We turned into a building–guitars, stereos, music equipment. Stacks upon stacks of CDs. Milk crates full of records.

Outside there were people playing music. An old man playing blues guitar under a tent. A band playing Metallica.

Eventually we wandered into the nucleous of Bio Bio–an area the size of a minor league baseball stadium that sits under a high industrial roof. Underneath it, tables of deodorant and soap. More toilet paper. Plants and rugs, record players and running shoes, vacuum cleaners. Screw drivers and power tools. Beats Audio headsets. One guy had a row of TV satellite dishes for sale (installation sold separately).

The crowds are intense and rival 4th-inning mobs at Fenway concession stands. It’s difficult to move around. I was suddenly exhausted. So I proposed juice.

We walked around the corner and took a seat at the counter in a Mexican restaurant. We drank natural juice smoothies and sat there for twenty minutes. Neither of us said much.

“That’s some serious shit in there.”

In a way, Bio Bio reminds me of a store near my college dorm in New York. Robin Raj on 14th Street wasn’t so much a deli, but more like a swap meet where we used to buy 40s. You could find anything there. Turkey sandwich, chips, a new blowdryer and a stapler. You’d be in there at 4AM, and see the counter guy packing brown paper bags full of beer, Phillie Blunts, and Doritos. They delivered right to the NYU dorms. A few years ago Robin Raj closed. A new 5 Napkin Burger has since taken its place. The East Village is hardly the same.

Los Condes and surrounding areas are the “new” and “rich” parts of Santiago. Instead of street vendors, they have the W Hotel and Brooks Brothers. TGI Fridays and Starbucks. Steel and glass office towers and the tallest building in South America. Sprawling supermarket chains like Lider, owned by Wal-Mart. Many Chileans are proud of this. It’s representative of the economic prosperity that has occurred here since the 1980s, the Chilean miracle.

Walking around this part of the city makes me kind of sad. I don’t see a miracle; I just see an imitation of LA or Minneapolis (a damn good one for what it’s worth). I avoid going up there unless I have to. It’s why I moved downtown. I much prefer Calle San Isidro and the street vendors and the weekend ferias.

If I have one complaint about my street, it’s Sunday. Everything is so quiet. Unlike their gringo counterparts, stores don’t open on Sunday. Outside of the ferias, it’s dead. It feels vacant and empty. It feels like my old neighborhood or the suburbs in Massachusetts. I welcome Mondays, when the vendors reemerge. When the scarf guy is outside the metro. Shouting, “Dos por una luca, luca, lukita!” That’s more like it.

Phantoms of Florida Street

It’s called the “Paris of South America.” In many ways it reminds me of New York. Sometimes, I think Beirut. Buenos Aires has everything—it’s my favorite city in South America (so far). It’s intense, diverse, and cocky; it has eclectic neighborhoods, a large artistic community, creative and interesting people. There’s an abundance of color. The Palermo neighborhood is like the East Village meets Havana–cafes, restaurants, bars, bright yellows, blues, and turquoises. People seem to smile more.

In Buenos Aires you can walk into any café, sit down, order an empanada off a menu you’re just seeing for the first time and a waiter—who looks as though he’s worked there for 30 years—will bring it to you, and you’ll take a bite and think it’s be the best thing you’ve ever tasted. There are food carts serving up choripan (like chorizo) sandwiches and 18 different kinds of mustard and salsa. Bife de chorizo in large quantities, all-you-can-eat steak restaurants, pastel de papas, vacio sandwiches, chimichurri everything, afternoon mate, malbec; excuse me while I go make a snack.

There is a sense of lawlessness in the city. Anything related to the government is in disarray. The streets are tattered, the streetlights are broken, its infrastructure is crumbling. Police are allegedly corrupt. Outsiders and Argentineans alike talk constantly about the corruption, about police officers colluding with criminals. When you arrive you immediately look at policemen with distrust; you are sure the policeman with a ponytail is crooked. You notice police officers talking with tattooed men on the street outside your hostel. Everything looks shady.

One evening I stumbled out of a nightclub in the downtown area at 2AM with James, a forgettable Australian traveler from my hostel.  We walked toward a line of taxis across the street with a vague notion about another club to head to that night. “Come on, let’s go.”

I approached taxi #1 when the driver looked at me.

“Reserved,” he shouted. He waved us away.

We walked to the next taxi.

“No, it’s reserved,” the driver said.

Third taxi, same result. That’s strange. Who reserves a taxi in Buenos Aires?

“They’re drug dealers, not taxis,” someone said. I looked at him. “You need to catch a taxi over there on that corner.” He pointed.


20 feet away on the street corner were two police women. I looked at them in their uniforms and again at the taxi line, which was in their sight. In a paranoid thought process, I imagined a vast corruption scheme involving 90% of the police force, politicians and local mafia.

A few more days in Buenos Aires and I learned the drug-dealing taxi line was not a unique occurrence. Many taxi drivers sold drugs, or maybe it was that many drug dealers drove taxis. What’s the difference anyway? They sold cocaine, ecstasy, and marijuana and drove you from point A to B.

This only added to Buenos Aires’ allure.

Due to an economic crisis, prices are low and fluctuate wildly; money feels frivolous. In a country with two exchange rates, rampant inflation and price volatility, money seems less important. Oh, about that. There  are two exchange rates: the official rate, partially pegged by the government, and an unofficial rate, the “blue market” rate, which is much higher. In February 2014, the blue-market rate price for goods was very cheap; at the official rate, they were also cheap.

A steak dinner cost $10, cigarettes $1, the best beef empanadas you’ve ever had, $1. There was inflation. One day your sandwich would cost $20 pesos; the next, $25 pesos. But it didn’t matter. When you’re dealing in these kinds of numbers, when the beer costs $1.50 instead of $1.25, who cares? I offered to pay for things, bought rounds of drinks, didn’t hesitate at any opportunity to go to dinner. I made it rain.

The crisis benefited tourists and destroyed Argentinean household wealth, another in a series of recent economic disasters. In between stuffing my face with $2 choripan and dollar empanadas, I felt vaguely guilty about the situation. Bankers use the word schadenfreude to describe a situation where one takes pleasure in the pain of others. This wasn’t that, but it did give me pause. The worse the economy got, the higher the exchange rate pushed, the further your dollars went, the more fun you could have. I’m digressing here.

Florida Street was where everyone went in Buenos Aires to change U.S. money on the blue market, as they call it. Florida Street is like Canal Street in New York without Chinese people. It’s crowded, touristy, full of knock-off goods and cheap food and street solicitors trying to sell you everything. Every few feet, there is someone shouting “Cambio?” “Cambio! “Cambio!” which is Spanish for “I want to buy your dollars, gringo.”

I walked down Florida Street for the first time with $200 in my pocket on a sunny afternoon. I needed to buy pesos to pay my hostel. I  was nervous, wearing sunglasses that shielded my hesitant eyes. I’d spoken with friends and people at the hostel about the blue-market exchange process. Everyone assured me it was nothing to worry about. “Everyone goes there,” someone said. “If you don’t change money on the blue market you’re a fucking idiot,” a Brit at the hostel said. “It’s no big deal.” Still, the back rooms, the unclear legality, the shady currency traders made me feel uneasy.

“Shalom, Cambio!” one man shouted at me. Another standing next to him did the same, “Shalom!” A lot of Israelis visit Argentina. I smiled and moved through the crowded street.

“Cambio!” another faceless man shouted. He locked eyes with me. “Where juu from?”

For some reason, I slowed. “Estados Unidos.”

“How much you want to change?”


“Small amount. $100 bills I can give a good rate.”

The traders preferred $100 bills because they stack easier in duffle bags and safety deposit boxes. Nonetheless, I wasn’t going to offer $100 because I was afraid–mostly of receiving counterfeit money on my first try, but also afraid of getting robbed or kidnapped.

“I only want to change $60. How much for that?”

The man took out a small calculator.

“11.50,” he said, showing me the digital display.

(The official rate was something like 7.2 that morning.)

11.50 was about the average rate I’d heard all morning walking along Florida Street. Moreover, the guy seemed harmless. You didn’t get a bad vibe from him.

“OK,” I said.

“Follow me. We have to walk one block.”

I followed the man off of the main street. We took a right onto a small side street and continued for another block.

“The rate is very high now.”

“Yes. Everyday it changes. Last week it crashed 40%,” he said and smiled. “We never know what will happen. That’s why we want your dollars.”

“Crazy.” My heart rate quickened as we continued walking for what felt like a long time.

I’d decided in Chile that small talk was a way to humanize myself in precarious situations. It was a way to make the guy think twice before kidnapping me, or so I figured. I did the same thing with taxi drivers, drumming up small talk, especially late at night, so that I did not seem as some faceless gringo the driver could rip off. It rarely seemed to work.

“Here, this way,” the man said, pointing to a passageway, which lead to an indoor mall. The metal gate at the entrance was halfway closed. We crawled under and walked inside and went into a small shop where another man stood behind a cash register.

The store looked like any other office I’ve been to. It resembled a travel agency or a waiting area at a dentist’s office. However, there were no products for sale; the shelves were bare. A radio played Top-40 music in the background. I stared at a man behind the cash register who was writing on a small notepad.

We walked up to the counter; “$60″ my new street friend explained. The cashier was expressionless as he took out bills from the register and counted them and laid them out on the counter. I handed him three $20 bills. I took the Argentine notes in my hands and, one by one, held each one up to the light and examined them, not sure what exactly I was looking for but feigning seriousness. The solicitor rested his elbow on the counter looking at his phone; the cashier continued writing. I maintained the same “serious” face I make in restaurants when a waiter presents me with a bottle of wine. The bills looked like the other money I’d handled; each one had a continuous strip and holographic face that appeared when you held it against light, similar to U.S. money. They seemed legitimate.

“OK. Thanks,” I said and folded the money and put it in my pocket. I smiled and thanked the men. They thanked me back. I walked out, unharmed, and put my sunglasses back on.

15 minutes later I followed a different street solicitor to a different side street, this time into store that sold baby clothing (of all things) and exchanged another $100 at a rate of 11.60/USD.

On my way back to the hostel, out of curiosity, I walked by the corner where I negotiated with the first man. He wasn’t there. A brief moment of panic, and then a test, I bought a soda with one of my new $100 peso notes. The money worked. They aren’t fakes I guess.

I went to Florida Street two more times that week, exchanging money in small increments. I never received a single counterfeit note; no one tried to rob me. It was just business. I found that I actually liked the process. The chaos, the negotiating, the preference for $100 bills, duffle bags full of cash, being part of an operation I’d read about in the news, the resemblance to the trading floor in New York, the people shouting, and haggling, the price volatility, the corruption, all of it, in a strange way, fueled my excitement and love for Buenos Aires. It was the same feeling one gets at craps tables in Las Vegas.

Each time I went back I’d look for the guys I’d exchanged with previously. I’d walk up and down the street looking for people I knew I could trust, but they could never be found. They were ghost-like, faceless figures, appearing in flashes, collecting U.S. dollars, and then disappearing. I was disappointed each time I couldn’t find my guy and had to find someone new. I didn’t like having to start a new vetting process, putting myself at risk each time.

Long-term travelers in Buenos Aires form relationships with blue-market dealers, or commonly trade with each other. They exchange phone numbers and send a text message anytime they want to make a trade. I told myself I’d do that next time. I tried to imagine what it’d be like to live there.

The blue market became popular in 2011 when the Argentine government imposed restrictions on its citizens from buying dollars. The aim of the measures was to slow the flood of wealth and foreign reserves leaving the country. Earlier the year the government lifted some of these restrictions, and banks are now authorized to sell small amounts of dollars. Over the past month, the spread between the blue market and official rate has tightened, and is now around 10.2 versus 8. When I visited it was around 11.5 versus 7. For further reading on Argentina’s economy, check out this article from The Economist. 

Conversation about Job Stuff

-“I need to create something,” he said. “I can’t continue doing a job where all I create are pitch books and loans.”

-“Why do you care?”

Why do I care? What does that mean?

-“Why do I care?”

-“Why do you care?”

-“Well, what am I here for? If it’s just to work in a bank so I can have nice vacations then I’d rather not be here.”

-“You mean that? Look around you. In the whole history of the world, it’s been about survival. Don’t be fooled to think that that’s changed today. Everybody out there is fighting to get what you already have. What are you going to do instead?”

-“Something, man. I don’t know.”

-“Let me explain something. My cousins in India make $500 a month. That’s about what I made per day last year. I know what the alternative is and I don’t like it. I know what it means to be where we are sitting. I think you’ve just lost sight.”

-“Actually I think everything is just now coming into focus. We don’t live in India. This is the United States. You really think that we all need to be so concerned about making money? I could do just fine with half the money I make. Shit, one third.”

-“Absolutely I do. Without question. Would you rather be rich or poor?”

-“That’s not what I’m saying. No one wants to be poor. Everyone needs a little money to live. Don’t you think there are other ways to get money? Do you really think we need to sacrifice everything for this career? So we can be top earners?”

-“What is it? You going to write music? You want to be one of these fucking waiters working here on the side? Act? Paint? Growing up outside of this country I can tell you that is not what the United States is about. There is no honor in that,” he took a sip of his drink and coughed. “What is it you want to do? Write about your feelings? You want to be Michael Lewis? Greg Fucking Smith? That’s it isn’t it. You want to publish those journals. Is that really what the world needs? Another ex-finance guy trying to get a book deal? Be realistic.”

-“Forget it.”

The waitress was standing 10 feet away. He moved his eyes up to her. “Could I have another?” Pointed to his margarita.


The Real World

“We don’t live in the real world,” a girl I’ve been dating recently told me. We were lying in bed on Wednesday morning at 10AM. I only had one class that day at 1 o’clock and as I got up to reach for my phone, her comment lingered in my head. I had heard this before, but all of a sudden I was offended. Technically, I had work that day just like everyone else. I still had to pay rent and worry about my bills and my student loans. Why didn’t my life live up to “real world” standards?

I suppose she was pointing out that it was 10AM on a Wednesday and we were still in bed and neither of us was at a desk job. And I suppose she was referring to my idea of work that day which was only one 90-minute class. And I suppose she was pointing out that “work” consists of teaching, which is essentially listening to my students speak about their problems or other topical things and correcting their grammar. I suppose all of these things combined, and the fact that I left a career job and that I live in Santiago, Chile, 5,000 miles from where I grew up make what I’m doing seem like it’s not “real” that I’m not living in the real world. I suppose.

The real world is synonymous with adulthood and taking responsibility for your bills and going out into the workforce and having the courage to live independently, out from the care of anyone else. Graduating from college and suddenly having to pay rent and student loans is like getting ice cold Gatorade dumped all over you. It’s a very real, expensive world out there. Finding a way to pay for the things you want is not easy.

Remember being a kid? Remember what that was like? Mom making you dinner, taking you to McDonald’s, asking dad for money when the slush truck rang outside your house, not having a care in the world about bills or any sense of responsibility? Sure, someone told you what to do all the time, and there were rules, but it was nice not having to do any of the work and sitting back waiting for your meals to be cooked. I used to spend summers playing baseball. My family would pile into the car on Saturday morning and we’d drive all over Massachusetts and I’d play a game or sometimes two and then I’d come home and mom and dad would buy pizza and buy some Coke and I’d sit in the pool and push myself around on a tube until after the sun went down when dad would turn on the pool light illuminating the water beneath me. And I remember just floating around there, not thinking about a whole lot, except my next game. Life was simple.

And do you remember as you got older how people started warning you about the real world that was going to crashing down on your parade? For me I had been hearing about it my whole life. I grew up in Fall River, Massachusetts, where adulthood equates to suffering. People would talk about business being bad, getting laid off from a construction job, having a tough time getting by, making life seem brutally difficult. My friends and family worked real jobs like running restaurants, working construction, bartending, and manufacturing. I had a great aunt who would take your simple “how are you?” small talk question at Christmas as an opportunity to tell you about her throat cancer and her granddaughter who’s getting divorced and about how she doesn’t have enough money to pay her medical bills. And I’d stand there at 9 years old sipping on eggnog listening to her, wondering if that’s what it’d be like for me. “Just wait till you start workin’,” she’d say.

When I was 18 and home the summer after my freshman year I agreed to take a job managing my parents’ café. It was a miserable job. I’d wake up at 6AM and pick up bread and bagels and open the place and run the cash register and clean up at 2PM after lunch. My first week, weary-eyed I pulled up to the Portuguese bakery off President Avenue and hopped out of my car and walked in to start carrying out the bags of bread, which were piping hot and already waiting for me on the counter. I was wearing a t-shirt and as I was running back and forth to the car I was thinking that surely it would be over 90 that day, perfect for the beach, and I thought about how I’d rather be doing that. Maria, the owner of the bakery, came out from the back and said hello and just as I was putting the last bag in the car, she noticed how tired I looked, that my eyes were barely open and she grinned and said, “Welcome to the real world.” She was standing in the doorway wearing an apron covered in flour, hair up and frazzled, grinning and looking tired herself. It was exactly like the John Mayer song, which in that instant made sense to me. I was miserable being awake at that hour and I shared her pain, and as I drove over to the café that morning I started worrying that this was what was in store for me; the party was over as far as I was concerned.

My father took note on days when I looked tired and bored because I never much took an interest in their business, and he’d say “It’s boring, huh. Doing this everyday,” and I’d just nod my head. And when I started working full-time in finance and I’d complain to people about waking up every day and doing the same thing over and over they’d simply say, “Sucks, doesn’t it?” and the words never sat well with me. As adults we envy the free-spirited, carefree lives children lead, not having to deal with real problems and real responsibilities. For me it was almost like everyone was just waiting for that day when I crossed over into adulthood so I could join them in misery and they could all smile and welcome me with an apron or a business suit or whatever it is I’d be wearing every day for the rest of my life. I pictured a party or a ceremony at the local banquet hall. My family would all be there and they’d be wearing their work clothes and they’d present me with gifts like a tie clip or maybe some business cards and congratulate me on joining them in the adult world. There’d be a cake, maybe some music, and we’d spend the afternoon talking about how we hate our jobs and I’d join them with some story about how I got laid off and about how I’m not sure how I’ll pay the bill for my kid’s tuition.

Of course, it’s not this way for everyone. You hear countless actors and musicians describe what they do as a dream, that it isn’t real, that they “can’t believe they get paid to do what they love.” Their life is a fantasy. Surely, if they’re having that much fun, it can’t be real. When they go to work in the morning they don’t say to their families “well, time to punch the clock,”…or ”hit the pavement,”…or “back to the grind,” or what I used to say to my roommate, “time to suck today’s dick.” Artists and musicians look forward to work, I think.

People sometimes can’t comprehend what I did leaving a job in finance to teach. Leaving New York for Santiago. I live in a different world 5,000 miles away now, and I’m trying out a new profession, but it’s real, sort of. I acknowledge, my schedule is unusual. I have large blocks of free time and sometimes I don’t work Fridays or go five days without working at all. Sometimes my work doesn’t really feel like work at all. But none of these things make it fantasy and not real. The only realness for me is that the job is temporary, that I don’t want to be a teacher for the rest of my life. That, and the fact that I don’t make as much money these days. Not the easy schedule, not the fact that I like the work, not the fact that I don’t find it as soul-sucking as finance, not the fact that I have energy when I finish a day, not the fact that I’m following a dream to live in South America—none of that makes me think what I’m doing isn’t real.

People who act or write music or play sports for a living or do something that they dreamed about doing are lucky. They do all the things we do, pay bills, support their kids, serve as parents, but because their job is so enjoyable and because they do what they want, we say they don’t live in the real world. Maybe they got lucky, maybe they caught a big break or maybe they just worked really hard to get where they are to make sure they never had to do a 9-5 at a job they hated. Whatever the reason, they made it through and they are the ones we, I, admire. What I admire is that their world is every bit real and that they created it that way.

Bob Dylan said “A man is a success if he gets up in the morning and gets to bed at night, and in between he does what he wants to do.” With no disrespect to Mr. Dylan, he’s only half right. A man is only truly successful if he does what he wants and finds a way to pay for it. Many people in America have jobs to pay for their lives and they live in big houses and they’re responsible, but their function, what they do every day, isn’t remotely what they want to be doing. They’re stuck in the real world. Contrarily there are more fortunate people with money, who live off their parents, or inherited wealth from some place. They get to do exactly what they want, but someone else pays. And then there’s the third kind of person who follows a dream, who struggles to pay their bills, but finds a way slowly over time. They don’t let personal finance discourage them while keeping at some goal. They find a way to flip the real world on its head and not be a product of it. They acknowledge real world problems and pressures, while still doing what they want.

The “real world” is only real if you let it be real and if you let it control you and dictate your actions and the job you have. By this definition, I suppose, I don’t live in that world. I escaped the real world, for now. I just hope I can stay there.

Something’s Come Up

Growing up, I did well in school. I got all A’s. In fact I don’t think I ever got a B, except for once in art class in elementary school. I was the valedictorian of my high school class. I played sports, baseball all the way up to varsity level. I was in the Spanish club. I was captain of the math team. I was in the honors society. I was class treasurer. I edited the high school newspaper. I got into a prestigious business school and did well there. I got a job right after graduation and started making six figures at 23. I lived in New York City. I rented a beautiful apartment in the East Village. My parents were always proud of me. I had done everything by the book and it had yielded some success. It was always my dream to be a responsible adult and make a lot of money. And then my dream started to come true, and I saw a way towards doing just that. From the outside it appeared that everything had gone according to plan. I had worked hard and everyone was so proud of me. My mother especially loved that I had gone off to New York, and she loved coming to visit and seeing what I was up to. “What a life you’ve got,” she’d say. And it was all very well and good. I only had one problem: I was miserable.

I didn’t become miserable over night. It happened slowly over time, as I kept on barreling down a path that everyone kept on telling me was good, and one that I stayed on because I listened only to what others told me. No matter what I did my family loved it. I’d come home at Christmas and my family would ask me what I was doing, and they’d all be so proud of me for working at a big bank and making a lot of money and traveling around the country to do deals. And every year as I got deeper into it, I started to think that maybe this was actually it for me. You could look at it in one way that the job I had was the product of my entire life’s work. Graduating at the top of my class in high school got me into the great business school, which got me the job that made me a lot of money.

I had inklings in college that maybe I should look at another career. When I’d fall asleep in the back of my corporate finance class. When I did much better in my liberal arts classes. When I realized there were so many people in the business program whom I didn’t like and didn’t want to be around. When going to networking events and interviewing got to be painful. I called my mother in the fall of 2006 to tell her all of this. I said I wasn’t doing well in accounting and I hated the class and that I didn’t find it stimulating. And she responded, “Well, how could anyone like that stuff?” And I started to think that in order to make real money, I’d have to sacrifice liking my job. And if I was going to such an expensive school, and I didn’t want to change that, then how could I possibly explore a career that didn’t bring in big money. And I kept finding ways to justify this life. If I’m going to do a job, I might as well do the thing that pays me the most money. Right? I mean a job’s just a job. Why not do something that pays you the most?

The economy collapsed in 2008 and the firm I interned for went bankrupt, but still I kept going forward. By then I was a junior in college, and it was too late to change anything, surely. Since there weren’t many jobs at graduation, I didn’t have many options. I started working in Westchester at a failing bond insurance company. I commuted one hour from New York City every day. And I worked there for about a year, and it didn’t crush me the way a banking job would, but it was a slow death. Mostly I found the work boring. And after a year, I hated it. I got to go home at 5 every day, and we had summer Fridays, and I worked less than my friends, but I decided that I needed to get out. The money was good, but that was another problem. It wasn’t accumulating fast enough. As I explained to my mother, “I’ll make $100,000 here next year, but it’ll stay that way for a while. I’m not going to get rich doing this.”

When I started looking for a new job, I considered money mostly and I thought of only one place to go, an investment bank. And so, I got a job at an investment bank in midtown Manhattan. It was the opposite of my first job. It was intense and I worked double the hours and made double the money. It slowly consumed my life, and I got caught up in it for a while. My parents would ask how I liked it, and I would tell them it was better because “I was facing clients. Doing deals for them. And I was eligible for the bonus pool.” They were happy because I seemed happy and because it seemed like I was doing something really important even though they didn’t quite understand what I was doing, and neither did I sometimes.

Still I had these feelings that maybe it wasn’t quite right. Slowly I started suffering from the stress, little twitches here and there, more talking to myself. I was working all the time. I was less happy every holiday I went home. I looked at others around me who had worked in the business for 20 years and I saw how unhappy some of them were and I felt like I didn’t want to be like them. And I thought to myself, well, this isn’t good. Because it wasn’t supposed to feel like that; it was supposed to be a happier place. I had worked so hard to get there. I had climbed the mountain and I was getting closer and closer to the top, and now I wanted to change it? Change scared me because when I started to think about it, I had no idea what I would do instead. I was already doing what I had “set out to do.” There were only a few other jobs that would pay me more money, and it would be hard for me to get those jobs, and further I wasn’t sure I wanted one of them. I started to realize that the money wasn’t going to make me happy. I could try another bank, but by the time I settled in over there, I’d be that much closer to 30, and there’s a chance I might be stuck in this world. But if I wasn’t going to work on Wall Street, what else was I going to do?

This question ate away at me for almost two years. I did everything I could to put my fast track plan in full reverse. It was as if I were on lookout for the Titanic and spotted the iceberg and called out and tried to turn my ship as soon as possible and put it in full reverse, but couldn’t quiet get it done fast enough. I obsessed over it, and it paralyzed me for a while.

When I finally found something I thought maybe I could try, teaching English, in Chile, I took another six months to go through with it. Even after I accepted the job to come down I kept interviewing at other “real” jobs as I called them. I spoke with consulting companies, startups and other finance jobs. I kept hoping that one of them would feel OK, but none of them did. I hoped that they would work out because that change would be easier to deal with. Even though I felt the jobs maybe weren’t for me, I wanted to go through with them. I wanted a job offer so I could feel confident and proud and keep achieving conventional things that my parents could be proud of. I didn’t want to have to deal with quitting my job to teach English, because that was basically an admission that everything I had worked for would need to be put on pause, that basically I would be starting over. And it was terrifying to think about that. Even at a young age, I was stuck in my ways. I was already solidified.

Three months after I agreed to come to Chile, and after delaying my start date several times, I decided to quit investment banking. I gave my notice on a Friday in June, and it was one of the toughest things I’ve ever had to do. I waited until after lunch to talk to my boss, nervousness pouring over me. As the words came out of my mouth and I told her about my plan, and she just looked at me, I didn’t feel any better. She told me about how she ran off to Africa once, but that was for two months “just before business school,” implying that I was crazy to run off without a plan for reentry. And I just said it was how I felt in my gut that I needed to do this, and she said “well, you have to listen to your gut.” I told another senior colleague that day, and since he liked me, he wasn’t happy and he was shocked at the words coming out of my mouth. “Something’s come up,” I said. “I’m leaving the business. I’m moving to Chile.” And then after that I had to call my mother and tell her the same thing because I hadn’t told my parents yet. It was all very tiring.

I went home to my girlfriend that night, exhausted. I didn’t have any plans and she could tell I was a little distraught so she let me tag along to dinner with her friend, and I just sat there the whole night, completely drained and feeling on edge. The feeling only got worse the next week when I had to start telling other people at my bank and other friends. “Something’s come up,” I’d say. And then an email went around the bank and my phone rang continuously over the next few days as it become public. And over and over I had to explain myself. People were supportive mostly, except for one guy who pointed out my poor timing, leaving mid-way through the fiscal year. But still I felt uneasy about the whole thing. I didn’t sleep much for a couple weeks and it was only after everyone knew and I got taken off some projects at work that I started to look forward and feel better.

The prospect of change was so terrifying for me that it almost prevented me from going through with it. The act of going forward with the change drained me emotionally and physically. I had been programmed my whole life to follow convention: work hard, get into college, get a job, stay at said job, get promoted. Stay the course. Quitting wasn’t in my vocabulary, and then all of a sudden it was. It was the first time in my life that I had made a major decision based off a gut feeling that wasn’t dictated by money or wasn’t conventional or wasn’t what my parents would have chosen for me. It was so far out there, and so frightening, and I wasn’t sure how anyone was going to react.

And so it was surprising that my mother was proud when I told her the news. “That’s awesome. It takes guts to do that,” she said over the phone. It was also surprising that many of my coworkers appeared envious that I was leaving for a new adventure. One senior banker even admitted he had been thinking a lot about his own life, and wondering if he should be doing something else. Suddenly, my change which seemed so out there, actually wasn’t that crazy at all, was actually something that others had considered.

I learned the change that I feared for so long didn’t have to be such a big deal. Ultimately I went through with my decision because I felt like I had nothing to lose. If I didn’t like Chile, I could come right back to where I was, and it could just be like I took a three month vacation. I realize now I didn’t have to be so afraid. I didn’t have to delay it for so long. When I felt those feelings in college, I should have listened to them. I learned the hard way that you can’t ignore feelings like that and just sweep them under the rug. They eat away at you, slowly, and over time, you have to deal with it, one way or another. When you consider the consequences of not facing a change, change becomes the easy thing to do. If you don’t love something, quit. It’s just that easy.