Like many people, I'm self taught in IT. This does mean I have large wholes in my knowledge base. I do my best reading books, Google is my friend, and most recently I persuaded work to actually send me on an actual training course.
My biggest problems are finding out what tool I need for a given job, and how to use a new tool. Assuming I've found the right tool, making it work can sometimes be quite a challenge. It's not that the documentation is awful, though it can be sometimes, rather that it assumes I know more than I do. Often all I need is an example, and then the documentation makes perfect sense.