catch 22 must be the gold standard here.

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far less prominently: i'm still proud of the points i scored with a lawyer by saying this one apparently-trivial lawsuit from a vexatious nutball could easily turn into bleak house. he thought i was catastrophizing, but it did get his interest enough taht he asked what i did for a living as we were wrapping things up. it was fun to give him an answer that people normally associate with the 'fiction is a waste of time' crowd ;-)

[i didn't hire him; and i turned out to be right).