How to be Poor and Happy in Havana
I lost my cash, cellphone and wife's patience on my first day in Havana.
I'd convinced the editor-in-chief of VICE to send me to Cuba, which thanks to the Obama administration was now open to American tourists for the first time in decades.
After collecting clips as a freelance writer, I landed my dream assignment: bumble around Cuba and interview people using my broken Spanish in the hopes of stumbling upon a story that might appeal to jaded millennials like me.
Still, once I lost my money and connection to the outside world, I realized the idea was half-baked.
Before I dropped out of journalism school, I was a disorganized and unprepared student -- and not-so-secretly proud of it.
I was also a cliche.
I devoured books by Hunter Thompson, Tom Wolfe, Joan Didion and the rest of the New Journalists.
Compared to shoe-leather reporting, their writing seemed like poetry.
Unfortunately, it made me think I could play fast and loose with supposedly boring things, like accuracy.
After dropping out of J-School, I managed to write for places like the Mercury News, Santa Cruz Sentinel, Interview Magazine and GQ -- and received an education from editors with no tolerance for arrogant, lazy freelancers.
Their words came rushing back to me while I sat on the bed at my hotel room in Havana.
"Most people go through life believing that how they experience it is how it really is," said Michelle Garcia, a journalist and former editor of mine.
"Your job is to disabuse of them at that notion."
Here in Havana, without Wi-Fi or money, I was getting a taste of what life was like every single day for average Cubans.
While some Americans might know that, how many of them know what it feels like?
What felt like a crisis was now a teachable moment.
Eventually, I borrowed a stranger's cell phone and called my dad, who wired me money.
After standing in a long, snaking Western Union line with dozens of Cubans for hours, I became intimately familiar with some of the country's people.
I asked them questions about life in Cuba while we stood there, both of us desperate for money from the States.
They invited us into their homes, where they fed us and told us stories of unimaginable hardship.
One was related to a powerful but corrupt politician.
Another was a doctor who drove a taxi to make ends meet.
By the end of the week, I had enough for a story about how the bitter U.S.-Cuba relationship played out in the island's streets.
The trip taught me about the importance of preparation, contingency plans and talking to people.
And trying to experience every bad situation as an opportunity to learn something about the world -- including me.
I'd convinced the editor-in-chief of VICE to send me to Cuba, which thanks to the Obama administration was now open to American tourists for the first time in decades.
After collecting clips as a freelance writer, I landed my dream assignment: bumble around Cuba and interview people using my broken Spanish in the hopes of stumbling upon a story that might appeal to jaded millennials like me.
Still, once I lost my money and connection to the outside world, I realized the idea was half-baked.
Before I dropped out of journalism school, I was a disorganized and unprepared student -- and not-so-secretly proud of it.
I was also a cliche.
I devoured books by Hunter Thompson, Tom Wolfe, Joan Didion and the rest of the New Journalists.
Compared to shoe-leather reporting, their writing seemed like poetry.
Unfortunately, it made me think I could play fast and loose with supposedly boring things, like accuracy.
After dropping out of J-School, I managed to write for places like the Mercury News, Santa Cruz Sentinel, Interview Magazine and GQ -- and received an education from editors with no tolerance for arrogant, lazy freelancers.
Their words came rushing back to me while I sat on the bed at my hotel room in Havana.
"Most people go through life believing that how they experience it is how it really is," said Michelle Garcia, a journalist and former editor of mine.
"Your job is to disabuse of them at that notion."
Here in Havana, without Wi-Fi or money, I was getting a taste of what life was like every single day for average Cubans.
While some Americans might know that, how many of them know what it feels like?
What felt like a crisis was now a teachable moment.
Eventually, I borrowed a stranger's cell phone and called my dad, who wired me money.
After standing in a long, snaking Western Union line with dozens of Cubans for hours, I became intimately familiar with some of the country's people.
I asked them questions about life in Cuba while we stood there, both of us desperate for money from the States.
They invited us into their homes, where they fed us and told us stories of unimaginable hardship.
One was related to a powerful but corrupt politician.
Another was a doctor who drove a taxi to make ends meet.
By the end of the week, I had enough for a story about how the bitter U.S.-Cuba relationship played out in the island's streets.
The trip taught me about the importance of preparation, contingency plans and talking to people.
And trying to experience every bad situation as an opportunity to learn something about the world -- including me.
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