jamesf comments on Self-Congratulatory Rationalism - Less Wrong
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What does brevity offer you that makes it worthwhile, even when it impedes communication?
Predicting how communication will fail is generally Really Hard, but it's a good opportunity to refine your models of specific people and groups of people.
improving signal to noise, holding the signal constant, is brevity
when brevity impedes communication, but only with a subset of people, then the reduced signal is because they're not good at understanding brief things, so it is worth not being brief with them, but it's not fun