A happy coincidence of The Praggies and O'Reilly both doing bookamajigs focused on general, programmery, learning. O'Reilly's is an interesting take in that it is a collaborative, wiki-based venture. Andy Hunt's is triply interesting to me as I did my graduate work on the stuff he is writing about, if in a very different context (formal education).
Refactoring Your Wetware starts out with a nice review of the Dreyfus model (I grabbed the beta book) but is still mostly not-yet-written, so Andy's approach to progressing through the stages isn't clear, yet. I'm very much looking forward to seeing how he approaches and presents the long view of learning.
The O'Reilly approach hits close to home for me as I spent a lot of time experimenting with material from the Portland Pattern Repository when I transitioned back into programmering from teaching and realized I didn't actually remember much! Anything that helps self-taught folks get better is teh win.