Why I Went to Cuba

I remember that day clearly. It was Thursday, December 18, 2014 when I stepped out to a brisk Dallas morning and into a Black Audi waiting to take me to Deep Ellum.

I was in town from L.A. on one of those uneventful business trips that dragged on longer than necessary. The night before, I had been shacked up in The Joule’s bar with a good friend/former coworker, drinking, talking and geeking out on ideas to making positive and progressive changes at the startup I was working for at that time.

As we drove off en route to Deep Ellum, I was recounting some of those initiatives to bring us forward, when I noticed a fresh copy of The New York Times conveniently placed in the pocket in front of me. When I pulled it out, the rest — as they say — is history.

The headline read:


I couldn’t believe it. I wasn’t even able to fully process what I was reading until a minute later. This was HISTORY. This was real positive change, real positive impact, and one that has been far from overdue.

After letting the awesomeness sink in, it dawned on me: That one dream I’ve been romanticizing and obsessing over for years is coming to fruition.

I’ve researched the interwebs high and low, read all types of literature and resources that only bestowed contradicting information; never providing one streamlined, accurate answer of how to get to Cuba as an American without involving too much risk.

For the longest time, I’ve dreamt about going to Cuba. Why? Because…Cuba! Is there really another answer? I was so excited, I Instagrammed the occasion.

Immediately realizing what this news meant and what it represented, I stopped caring about risk. I was going to get to Cuba. I had to. Because now, the real risk wasn’t the possible implications of having a stamp from Jose Marti airport — The real risk was missing out on discovering and immersing myself in a world left at a standstill and experiencing all of what that wondrous country had to offer, before the floodgates eventually open and changes everything forever.

It was a race against time and 33-weeks after Instagramming the front page of the New York Times with the accompanying caption, “The only news I like. See you in Havana!” — I did just that.

I was landing at Jose Marti Aeropuerto for what was the beginning of the most spectacular aventura I’ve had thus far.

I made it to Cuba.

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