Caveat: I don't know Rails. I've only recently started teaching myself to code/program/develop. So I guess now is a good time to start with Rails as any, eh?
8 months ago I jumped straight into working with Django/Python - one fine day, I made a list of project ideas that I've had in my head for a while and started chalking out the corresponding algos & coding them without a care about how 'bad' my code was going to look. (Yeah, I belong to the 'learn first, refine later' school of thought.)
8 months since I first started, the score is two ideas done, six more to go. Wait, scratch that, seven more to go. Wish me luck!