Several weeks ago I wrote a heavily upvoted post called Don't Be Afraid of Asking Personally Important Questions on LessWrong. I thought it would only be due diligence if I tried to track users on LessWrong who have received advice on this site and it's backfired. In other words, to avoid bias in the record, we might notice what LessWrong as a community is bad at giving advice about. So, I'm seeking feedback. If you have anecdotes or data of how a plan or advice directly from LessWrong backfired, failed, or didn't lead to satisfaction, please share below.
Using terms that I picked up here which are not well known, or mean different things in different contexts
Also, I sometimes over pattern match arguments and concepts I've picked up on Lesswrong to other situations, which can result in trying to condescendingly explain something irrelevant.
I do something similar. I consistently massively underestimate the inferential gaps when I'm talking about these things, and end up spending half an hour talking about tangential stuff the Sequences explain better and faster.