Would you do this?

Later tonight I’m heading to the Caribbean for a weeklong sailing trip around the British Virgin Islands. I’ve sailed before, but only in the Bay Area, and never on an overnight trip, so suffice it to say I’m pretty excited for the adventure.

“How’d you get invited on this trip?” Friends inevitably asked whenever I mentioned the trip.

“An ex-coworker invited me,” I explained. “I’d see him post these amazing sailing vacations on Instagram and I would always like or comment on his stories…I think that’s how I got invited.”

“Who else is going with you?”

“I don’t know,” I admitted. “It’s my friend, his partner, and a group of their friends. Honestly, I didn’t care much about the details — it’s a once-in-a-lifetime opportunity, and I’m just going with it.”

“I can’t believe you agreed to something like that without knowing the details,” Charlene said.

“Seriously only extroverts do that,” Karen chimed in.

I shrugged. “I’ve seen enough of his Instagram posts,” I said. “I’m sure it’ll be fun.”

Charlene wasn’t convinced. “Getting trapped in a boat with people you don’t like isn’t fun.”

Her reaction surprised me, and I started wondering: what was wrong with them? Was this an extrovert vs. introvert thing (even though I’m a slight introvert and Karen/Charlene were the opposite)? Or maybe a guy vs. girl thing? Or even a Perceiver vs. Judger thing for all your Myers-Briggs fans out there? 

Later, I ran it by Jason, another good friend who I’ve traveled with many times. “I think it’s because you’re accommodating when you travel,” he said. “Some people aren’t.”

That sounded right to me. Over the years I’ve planned less and less for my trips, and I’m usually fine adapting to whatever comes my way. These days I rely on my stomach and camera to guide the way, since in the end it’s all about the vibes and the ‘gram. So even if this trip turns out to be a disaster (which I doubt), at least my Instagram will be fire and I’ll be soaking in the Caribbean sunshine. And honestly, that’s good enough for me.

The only details I knew about the trip (along with the dates/cost) when I enthusiastically agreed to go.
The last time I got to hang out with Jeremy was also on a boat (NYC in September 2022).

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