I have found the hardest part of self-learning to be finding peers and mentors, but I live in a technological wasteland.
The internet has made it easier, but it's not the same. When I socialize with friends, they don't care to talk about programming. In fact, they make fun of me.
I've found StackOverflow to be extremely helpful when learning about programming. It fills in the gaps and complements textbooks, API documentation, and building stuff on your own nicely. Many times I've even answered my own question before pressing "Post Your Question".
I have found the hardest part of self-learning to be finding peers and mentors, and I work in a software mecca. When I have lunch with colleagues, they don't care to talk about programming. In fact, they make fun of me.
I think there may be a selection effect where many of those who are really hardcore are too busy doing to socialize. Besides that, it can be hard to communicate with others about programming because there is so much disagreement about how to do it "right". (Not that there isn't also agreement.)
#haskell. I go there to ask math and compsci questions as well as stuff on Haskell itself. Sorry for not being the actual person you addressed the question to but #haskell is a really great channel, I didn't want you to miss out.
Most user groups that I know of are purely for "networking" or to push for a sale of the latest book. But sure- a meetup like the one for clojure in bay area/NY might be enlightening.
This one is deceptively important. I spent several years self-learning actuarial science. I had a solid statistics and math background, but incorrectly marginalized the business aspects as being simple. I'm also introverted and stubbornly independent and didn't recognize what I didn't know. If I had more aggressively sought out peers earlier, I would have gotten further.
I'm going against my nature and meeting with a friend weekly to review queries for a SQL class we're both taking. Just talking with him and catching each other's mistakes has been worth as much as my O'Reilly book.
The internet has made it easier, but it's not the same. When I socialize with friends, they don't care to talk about programming. In fact, they make fun of me.