The Story of Why I Write So Much About Puerto Rico

I just got back from my fourth working trip to Puerto Rico. The first was in June 2015, when I went down to write a story about chef Paxx Caraballo Moll for Munchies. My editor there asked if I’d want to also explore piña coladas, and why would I say no to that? Both pieces required me to do my own photography. Each paid a measly $150. But I wanted to start travel writing, and I wanted to tell Paxx’s story after becoming obsessed with their food via Instagram, so down I went.

I paid for the flight with accrued JetBlue points—thus, it was free outside about $12 in taxes—and booked two nights at the Dreamcatcher Hotel, which cost $177. I also rented a bike for about $60, had to pay for taxis in order to do the piña colada research, and also spent money on taxis to and from the airport as well as incidental food. In the best-case scenario here, I broke even.

That was fine, because I had a full-time job at the time and was trying to establish myself as a writer. The stories were pretty successful once they were published, so I went on to use that leverage to do more writing—for Munchies and for other outlets—and I quit my full-time job to take a $30 per hour contract editing gig at Food & Wine to get deeper into the world I wanted to be in. From the contacts I made while in Puerto Rico, I ended up writing about 5 or 6 more stories (like this one and this one and this one), which allowed me to actually make a tiny profit on the trip—that took months and a lot of work, though, and wasn’t even much (Eater paid $225 after months of back-and-forth; the F&W Q&A paid nothing because I was working there at the time).

One day, an email drops into my inbox asking if I’m ok working with brands. I’m curious and still itching to move into full-time freelancing, so I say I want to hear more. It turns out that [famous rental car company] has hired this marketing agency to create a magazine for them filled with travel content, and this marketing agency guy has found my writing on Puerto Rico and would love to send me back to write more. They reimburse all my expenses and, on top of that, pay me $4K for what ends up being 3 pieces and a lot of original photography.

Thus, the first trip earned its worth back and then some. On the trip for [ famous rental car company], I get to talk to way more people and establish further connections. I sell some more stories about the island. In the meantime, I quit the contract editing gig and take a part-time editorial job with a food magazine that allows me a lot more freedom to do what I want. [Famous rental car company] sends me to Detroit to do the same thing I did in Puerto Rico. It’s dope.

For my next working trip, I am flown down to speak at a conference of publicists about how to better work with journalists on sponsored content, where I get insane stage fright and forget literally everything I meant to say and was rehearsing in my hotel bathroom, and feel terrible. But, I did have a very good time getting extremely drunk on my first night and sell a story about a bartender who moved to the island from the mainland for $150.

This brings us to this week, which kind of brings me back to the first trip: I really wanted to write a meatier story for an outlet I hadn’t been able to break into thus far, so I used JetBlue points again. This time, though, I finagled two free nights at very fancy hotels where chefs made me extremely extensive vegan tasting menus because I now have connections to work. I paid $100 for a third night at a very not fancy hotel after all AirBnB options were already gone (and frankly, the fun of AirBnB is gone and I don’t want to have to follow anyone’s treasure map to get keys just so I can sleep ever again).

Because I have so many friends and acquaintances down there now from all these trips, I am able to have an excellent time when not researching my piece and spend a lot of money getting a tattoo and drinking at new-to-me bars and buying the trinkets of local artisans, so in the end I will not make much money if any on this piece, which is paying $300 for the writing and photos. I’ll also do a “where to eat and stay” in San Juan roundup, and maybe I’ll come up with some other stories I can try to send out, but at this point, the trip is its own reward—to the place that allowed me to build the life I wanted for myself by being so kind and generous to me, to the place that fixes the fuck outta my soul once I step out into its air.

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