Rochelle left a comment on one of my entries that I think is important enough to bring up and highlight:

[P]eople are scared to try things. They’re always afraid of breaking something by clicking the wrong thing. I think it’s part embarrassment and part shame. That lack of playfulness hurts people too.

This is totally spot on.  We need to change people’s mindsets to make them comfortable fooling around, making things, breaking things, and playing on the web.