utf9k/vacations:
+1 due
         
or pay $5
I'm bad at taking time off

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This goal has the following fine print specified by utf9k:

I have to book at least 5 consecutive days off to qualify as a "vacation"

The point can be marked as soon as it's booked, rather than necessarily when I'm embarked.

Intent is what matters most here.

Goal is set to 3 but understandably, vacations may be shorter or longer so this may be more or less reasonable depending on the length of the breaks.