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Douglas_Knight comments on The Sin of Underconfidence - Less Wrong
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Overconfidence is usually costlier than underconfidence. The cost to become completely accurate is often greater than the benefit of being slightly-inaccurate-but-close-enough.
When these two principles are taken into account, underconfidence becomes an excellent strategy. It also leaves potential in reserve in case of emergencies. As being accurately-confident tends to let others know what you can do, it's often desirable to create a false appearance.
The cost of underconfidence is an opportunity cost. This is easy to miss, so it will be underweighted--salience bias. This is not a rebuttal, but it is a reason to expect people will falsely conclude that overconfidence is costlier.
I approve of your response, Douglas_Knight, but think that it is both incomplete and somewhat inaccurate.
The cost of underconfidence isn't necessarily or always an opportunity cost. It can be so, yes. But it can also be not so. You are making a subtle and mostly implicit claim of universality regarding an assertion that is not universally the case.
A strategy doesn't need to work in every possible contingency to be useful or valid.