Career conundrum: how to weigh that gut feeling?

The other night as I was falling asleep, a situation occurred to me that struck me as something of a conundrum. (Remarkably, I still remembered the situation when I woke up.) I’ve been working out my own take on this situation — what’s at stake in responding to it one way or another — but I wanted to canvass the commentariat for responses before I put my own analysis out there.
Here’s the situation:

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