Classic! I always thought that there should be a course (ideally starting from middle school but definitely in college), perhaps called Life Engineering, where kids/young adults are taught tools to help them shape their lives. Alongside this, pg's essay "What You Wish You'd Known" (http://www.paulgraham.com/hs.html) and Randy Pausch's "Last Lecture" (http://www.paulgraham.com/hs.html) would be included in class materials.
This class should would also teach you important little life skills like how to tie your shoes better using the Ian knot (http://lifehacker.com/5451765/ditch-the-granny-knot-to-tie-y...), how to match clothing items so that you don't look like a total clown (unless intentional), how to write legibly with proper handwriting, etc.
I don't know about the shoe-tying, but yes, this would have been great.
How to talk to people you don't know, how to consider what other people are thinking, how to nourish healthy relationships (and the many possible options for not-so-healthy relationships). Practice semi-public speaking. How to become an "expert" on something.
I think many of "how to your life" type classes might run afoul of parents' preferences, though, for younger students (how to talk about religion?), and run into the limitations of the professors for older students -- professors aren't necessarily good representatives for interesting and unusual life choices, especially if they're never really left academia since they were students themselves.
Of course we're going to reinvent the wheel using tech-industry terms here on HN. :)
One of the points that DFW is getting at in this speech is that this is exactly what a classic liberal arts education is supposed to do for you (ideally). But both the ideal and the practical reality of that education have suffered terribly at the hands of social institutions that see education primarily as an industrial input and higher education as a credentialing tool. And it's a bit of an uphill fight against some of the less-enlightened sides of human nature to begin with.
I wish I had that kind of class growing up. Even a basic life skills class would be helpful. It would be much better than all those "teachers aide" classes I took in high school.
This class should would also teach you important little life skills like how to tie your shoes better using the Ian knot (http://lifehacker.com/5451765/ditch-the-granny-knot-to-tie-y...), how to match clothing items so that you don't look like a total clown (unless intentional), how to write legibly with proper handwriting, etc.