My path so far with javascript (with examples!):
Desire to make neat web pages. Learn enough jQuery so that you can make something move and change colors with maybe two lines of javascript instead of 20. Keep trying to one up yourself in what kinds of cool shit you can make (I use the term shit because you won't be making anything useful persay, but it will be something that will make friends say "Shit, that is cool. How did you do that?")
Start to learn more and more jQuery until you think in callbacks and events.
Use the canvas to make weird patterns (treeowls.com).
Make something using Ajax (try the hnsearch api: pretty fun http://zacharymaril.com/HNSearch/Topics/testing-api.html).
Try to solve a hard problem with JS that requires lots of computing (some work with Ramsey theory: http://zacharymaril.com/thoughts/constructionGraph.html) .
Mess around with Three.js (http://mrdoob.com/blog/post/693) and Processing (http://zacharymaril.com/).
Use chrome or firefox with the debugger.
Then get bored with frontend stuff and jump into node on heroku or whatever hosting service is popular but has good documentation. Make a chatroom with a lazy bot(zackbot.com) and a static file server. Look into the database bindings. Look at the stuff DailyJS puts out on node(http://dailyjs.com/tags.html#lmawa old with bugs, but very in depth for the time). Make something neat (still working on that part).
Read a bunch of Javascript/jQuery blogs. If you learn that way, pick up JS The Good Parts. Read anything/everything by Steve Yegge, John Resig, and Ryan Dahl. Use the jquery documentation from the website, then get frustrated with it and use jqapi.com
But that is all based on one approach. It sounds like you are interested in more backend stuff. Starting out with node would probably be what you looking for, but without much know how of how to make things work, you might not get thrilling enough results to actually stick with it. I would say stick with the frontend to learn how javascript works and where it came from and then when you get really really bored go mess around with node.