I could write a thousand lines about what why the lucky stiff did that was right. There’s no need, though; I need only point you to endeavors like teaching Ruby to high school girls using his Shoes framework and, more importantly, his attitude of learning, grappling with complexity and exploring concepts through play.
Every once in a while the rest of the world turns to the question of why there’s so few women in programming. Besides the obvious nit-picky answer (there isn’t few women, there’s just fewer women, i.e. non-parity), the answer is that learning how to program is a goal far behind the entrance points a young mind might see (how do I make a game?) with dusty, academic, uptight paths connecting the two. A certain kind of people are over-represented in programming today, and that’s the kind that can form this connection early on and persevere. (I don’t know about the gender balance in this group and it doesn’t interest me; I just think that this monoculture is getting a bit frustrating.)
The way to get more people into programming, and the way to get people who can infuse programming with new ideas and approaches, is to short-circuit this. Young people may not see the computer as unfriendly, but that doesn’t mean they see it as malleable or controllable. Make the connection fun and obvious, turn on the lightbulb with regards to the connection between a written script and the computer’s actions. People who make this connection early are excited and electrified and passionate because they still think it’s awesome magic that they now know even more about. Every issue in their way becomes a challenge to overcome and master; they are far less likely to give up and ask around blindly.
This isn’t rocket science; it’s already the way we all learn human language. So certainly, a bit more Ruby and several tons less Java, C++ and linked lists, please, but first and foremost, a little less Ruby and a bit more “radical” thinking.