This is one reason I'm joining Dev Boot Camp for the summer session. I think all the people and support will help push through all the blocking points of learning programming

also see: apple, twilio, ikea

Nice thought but how do you engineer such a thing?

I think Zynga does it pretty well, and they do it in the same most web apps do it (that get it). You walk people through your web app exactly how they should use it.

You make them pass every ideal step before you allow them to move on to the next one (unobtrusively).