I've personally struggled with this; as a young teenager, I tried to learn C++ without any access to the internet, any mentor; just a few old books. I struggled with it for years and ultimately failed because certain technical obstacles couldn't be overcome without "in-group" knowledge that didn't exist in the meager documentation I could find. Either you were part of the social group that could help you out of your problem, or you effectively were not privileged to use the technology.
IRC is symbolic to me of this sort of old-school "it works fine for us" mentality that poisoned the early tech enclaves - their myopic failure to include anyone who didn't win the social lottery of knowing the right people, or growing up in the right place. It's not that it worked for them that I begrudge - it's their assumption that things must also be working for the rest of humanity, since they themselves were doing just fine. It's the same sentiment that made people hate the classic "let them eat cake" line.
(As a corollary, this is why Stack Exchange is maybe the best thing to happen to tech since the internet - a system specifically designed to incentivize people to document all of those "undocumented secrets" that are necessary to actually get any work done in a given field.)