My most interesting goal right now is to try to make the time to start moving off of Microsoft development technology. I like C#, but ASP.NET annoys me and the whole platform feels like a massive dead end unless I want to work on boring corporate stuff.

My primary roadblock there is trying to decide what tech I want to pick up. Ruby and Rails are appealing, Python looks interesting, and I wonder if I shouldn't be looking at some new stuff like Clojure or node.js as well. I also wonder if I shouldn't get into some of the evented frameworks like Tornado or EventMachine. This has always been my problem -- I'm interested in too many aspects of technology and there's just no time to pursue them all.

My secondary roadblock, once I decide on a tech, is getting some good documentation and perhaps some mentoring on it. Some of those frameworks seem to be pretty lacking in good documentation and examples.