People don't realize that the hardest part of being a Rails programmer is being humble.
When I decided to learn Rails, I said to myself, OK. Here's this thing somebody younger than me made, which is much more successful than anything I've ever done. (And already at that time it was.) So this guy must know some things I don't, and more than that - this guy's way of thinking about the Web works better than my way of thinking about the Web. So what I really have to do is stop thinking about the Web the way I used to, and instead learn to think about the Web in the way that DHH thinks about the Web. So how can I figure it out?
I think most people wouldn't be able to do that. I had to re-examine all my assumptions about how to build a Web app, and that's a lot to do. To really re-learn what you already know? It takes incredible humility, and most people just aren't as humble as I am.