wedrifid comments on Rationality Quotes December 2012 - Less Wrong
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Unless, say, you're going to overwhelm a critical position with superior numbers and superior technology at a tactically convenient time.
In some such cases being utterly predictable even has benefits. People who know they are going to lose and die if they fight are more inclined to surrender or flee. (This has obvious advantages if you are a pirate with a fearsome who doesn't want casualties.)
That actually sounds like solid advice in most situations. (Assuming 'fail' excludes 'weakened them significantly but did not quite defeat them'. Obviously a second attack then should be evaluated as a different approach.)
Yes. The whole thing should be read as elaboration of one piece of advice - the individual sentences are not meant to stand on their own. If you're overwhelming the enemy with multiple attacks, then none of them should be counted as failure.
And FWIW, Musashi was primarily writing about swordsmanship, not command.