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KPier comments on Rationality Quotes September 2014 - Less Wrong
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This is not the whole story. In the quote
you're paying too much heed to the final clause and not enough to the clause that precedes it. The shipowner had doubts that, we are to understand, were reasonable on the available information. The key to the shipowner's... I prefer not to use the word "guilt", with its connotations of legal or celestial judgment -- let us say, blameworthiness, is that he allowed the way he desired the world to be to influence his assessment of the actual state of the world.
In your "optimistic fellow" scenario, the shipowner would be as blameworthy, but in that case, the blame would attach to his failure to give serious consideration to the doubts that had been expressed to him.
And going beyond what is in the passage, in my view, he would be equally blameworthy if the ship had survived the voyage! Shitty decision-making is shitty-decision-making, regardless of outcome. (This is part of why I avoided the word "guilt" -- too outcome-dependent.)
The next passage confirms that this is the author's interpretation as well:
And clearly what he is guilty of (or if you prefer, blameworthy) is rationalizing away doubts that he was obligated to act on. Given the evidence available to him, he should have believed the ship might sink, and he should have acted on that belief (either to collect more information which might change it, or to fix the ship). Even if he'd gotten lucky, he would have acted in a way that, had he been updating on evidence reasonably, he would have believed would lead to the deaths of innocents.
The Ethics of Belief is an argument that it is a moral obligation to seek accuracy in beliefs, to be uncertain when the evidence does not justify certainty, to avoid rationalization, and to help other people in the same endeavor. One of his key points is that 'real' beliefs are necessarily entangled with reality. I am actually surprised he isn't quoted here more.