Ruby on Rails Roadmap

I respectfully disagree. For someone without development experience, I
wouldn't recommend learning yet another language on top of Ruby and
Rails. In fact, I would say that a better starting point would be
Sinatra (and erb templates). This allows someone familiar with HTML and
CSS to ease into learning Ruby but at the same time getting the instant
gratification of seeing dynamic content in their pages. For those of us
who have been immersed in software development for a while, it's easy to
forget how steep the learning curve is.