Mark Friedenbach's post Leaving LessWrong for a more rational life makes a few criticisms of the way LW approaches rationality. It's not focused enough on empiricism. While he grants that there's lip service payed to empiricism Mark argues that LW isn't empiric enough.
Part of empiricism is learning from errors. How do you deal with learning from your own errors? What was the last substantial errors you made that made you learn and think differently about the issue in question?
Do you have a framework for thinking about the issue of learning through errors? Do you have additional questions regarding the issue of learning through errors that are worth exploring?
I agree that LW tends to be heavily skewed toward reasoning over modeling, looking for counterexamples and other forms of testing. In fact, it's not uncommon to see "explaining away" as a reaction to counterarguments. "Clever arguer" is a common pitfall among people used to thinking of themselves as smart.