Ruby on Rails Roadmap

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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.