Given how well both of them have done, at least up to today, it actually seems like evidence he was underconfident if anything. If they were independent events, the one in 10 for each of them might be like a one in 100 that each of them would do this well. And that's given the low odds he assigned, I think that suggests maybe he was under Confidence. But in this particular sense, I think yes, he was.
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What are "scout" and "soldier" mindsets? How can we have productive disagreements even when one person isn't in scout mindset? Is knowing about good rationality habits sufficient to reason well? When do we naturally tend to be in scout mindset or soldier mindset? When is each mindset beneficial or harmful? Are humans "rationally irrational"? What are the two different types of confidence? What are some practical strategies for shifting our mindset in the moment from soldier to scout?
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