Choosing a Late Night Adventure

My very favorite aspect of working for myself is that I mostly set my own priorities about what to do with my time. And once any must-dos are completed, I try to opt for what will bring the most joy.

But I also really love me a good night’s sleep. Which is why, a few weeks ago, I faced a difficult choice: should I get up in the very wee hours to go congratulate Hound on finishing the Caribbean 600, even though it would inevitably degrade my next day’s writing and wingfoiling? Or should I skip it, since my presence was actually not required?

Hound’s crew enjoys their official Caribs after finishing the 2024 Caribbean 600

When I woke up at 130am and checked the race tracker, it predicted a 2am finish—the perfect kick of adrenaline to get us out of bed and dressed. After driving across a dark island dodging tire-popping potholes, we rolled into the slumbering Catamaran Club just in time to spot Hound’s distinctive lights steaming across the harbor. Minutes later she was backing into the dock, moon illuminating those classic lines and gleaming varnish—as well as the smiles of a tired but satisfied crew. 

We were soon joined by the official race greeters, who meet every finisher for a “banner photo” (and also swap a case of cold beer for the boat’s tracker). I haven’t seen any official pictures, but it was their photographer’s flash that enabled Paul (who didn’t have one) to successfully capture the moment.

On the drive home, he told me that “I didn’t know what to say.” But we didn’t need to say anything, because we had made the right choice: to be present for an occasion that we’ll reminisce about for many years to come. They say we only regret what we don’t do, and I’m very glad that I chose special occasion over slumber that night. As the cruise ship wife told her husband in a memorable Jimmy Buffett song, “Morris! You can sleep when you get home!” 

The next day was indeed a bit fuzzy, but my adrenaline kept me going right through work, wingfoiling, and that evening’s prizegiving—when we got to cheer the boat’s second Caribbean 600 podium finish. Thanks to the Hound family for letting us share their joy, even if my photo of the prize giving wasn’t up to standard. 

(Aren’t you glad there were official photographers to better capture this moment?)

Got a special moment when you made the right choice about where to be, or a regret about staying in bed? Share it in the comments below, or send me an email. And for more about choices and the many joys of self-employment, make sure to subscribe so you never miss a Thursday blog. Thanks!

2 Replies to “Choosing a Late Night Adventure”

  1. Fully agree it was great to be there at the dock. All the smiles, such a fantastic team to be around.

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