It’s a choice to defend a position, the hill, which makes no sense to expend all your effort on. It’s a generic reference to the idea that some territory would be worth dying over. If it’s a strategic important place then sure, defend it to the last man. Say if it’s your insistence that democracy or communism or something impactful is the right choice and the argument impacts whether or not it happens, it’s a sensible hill to die on. A weird hill to die on is something like getting into a heated argument over Star Trek vs Star Wars to the point it hurts your friendship with the other person.
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