I've "shared" a post by Jim Manzi at the American Scene, extensively criticizing Obama's graduation address at Wesleyan. I don't necessarily share his criticism, but I am ambivalent. But it seems to me that JFK's "ask not" line was criticized at the time by some on much the same grounds.
Note: I comment on Manzi's post, challenging the $14,000 figure for college graduates. Briefly, Obama had 2 years work experience and could easily have qualified as a GS-7 at about $17,800 if he had wanted to work for the government.