Warning, link dump ahead.
Start with:
http://tryruby.org/
Then try:
http://railsforzombies.org/
Other people have asked the same thing and received helpful answers:
http://www.reddit.com/r/rails/comments/dchql/what_is_a_great...
http://ask.metafilter.com/165590/Rapid-Ruby-on-Rails-indoctr...
http://stackoverflow.com/questions/55574/learning-ruby-on-ra...
Free programming books here, there are some RoR examples:
http://stackoverflow.com/questions/194812/list-of-freely-ava...
Rails tips:
http://railstips.org/blog/archives/2010/10/14/stop-googling/
(I liked this article but the whole site might have good resources.)
There is a community specifically for mentoring:
http://www.railsmentors.org/
And here's a general Rails community link:
http://www.workingwithrails.com/
Not my favorite site but here's a good article on freelancing:
http://www.smashingmagazine.com/2010/10/26/successful-freela...
Rails Rumble, get some app ideas from here once you build your skills:
http://railsrumble.com/
Of course, Google "_why". Read about "why the lucky stiff". Read lots about him and see where it leads you.