Heaven and Hell…Aka Grand Cayman

Okay, I’m finally going to write about the Grand Cayman trip. Here we go.


I found on New Year’s Eve that I’d been chosen to attend my company’s CEO Summit. Essentially, I had two good sales years where I made my goal, which, by some measurement of performance over time, placed me in the top 10% of sales professionals company-wide. I’m not quite sure how that happened, but if the result is a free trip to Grand Cayman, I don’t really care.


Everyone could bring a guest, so, since I don’t get to see her nearly enough, I asked Christina. She was going to be in Boston the preceding weekend anyway for her sister’s graduation, so she stayed in Boston a night longer. This was during the two weeks post-fire when I wasn’t in the sublet yet, so we got a hotel room near the airport. I figured out how to stream the Mad Men finale online (even though we had to be up super early for our 6 AM flight the next day, there was no way I was missing it), and the next morning we were off.


I knew the trip was going to go well when we got to the hotel and, within about five minutes, someone handed us a free rum punch.


There were, I think, a total of eighty-eight people from sales there, plus a bunch of higher-ups and everybody’s guests. There were a handful of people I’d met in passing before, but no one I knew well. They were from all over the place—all over the country but also foreign countries. I met people from Australia, England, and Tunisia, among other places. I met a lot of people from LA. Other than some managers who work in the Boston office, I was the only person from Boston there. I was also one of the youngest people, which was weird—in the office in Boston, I work with people who were born in the 90s and don’t have the same pop culture touchpoints as me. And I’m almost positive I was the only person there who was both single and childless. The vast majority of people brought their significant others and most of those who didn’t either brought one of their kids or at least had a significant other back at home. I’m pretty sure everyone thought Christina was my girlfriend until we explained that we were friends who lived on opposite coasts.





But most of the colleagues and guests that I met were really nice and interesting. On Monday, Tuesday, and Wednesday there were mandatory dinners that we attended with everyone at the summit, one of which culminated on releasing these lanterns over the ocean. We also had went on a couple of sponsored activities with colleagues. One was a sunset boat cruise on our last night there. The other was a trip that included snorkeling and a visit to Stingray City, where you can swim with stingrays!


Christina and I also rented a cabana and spent a whole day there, lounging on the beach and having food and drinks brought to us.


On another day, we went to Hell. Literally.


Yep, Hell is a rock formation in Grand Cayman. There’s even a post office so you can send post cards from hell. Christina sent one to her dad’s church.


Also, free booze. SO MUCH free booze.


It was an awesome trip that came at the perfect time—and it was all free since it was a work trip!

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