What do we define as "The American Dream"? The house, the yard, the picket fence, the 2.5 kids, and the dog? Or just the ability to find your niche and run with it? I think that makes a difference in this discussion. I believe society changes in relation to The Dream whether or not they want to. The Dream of working at one career anymore is, I think, dead. The Dream of working to live (rather than living to work) is dying. And I think we've been creating a chasm of social mobility that soon will be difficult or impossible to cross. America already offers less social mobility than many other countries.
Entitlement -- the belief that you did deserve something -- is a change that started with our parents, who expected Social Security and Medicare to pay out well beyond anything they had paid in. It's an expectation brought on by a long tail of prosperity fueled by cheap resources that led workers to believe they would always be paid more next year.
I agree that anyone who thinks they don't deserve anything probably will do fine. But when people attend Tea Party rallies and carry signs telling the government to keep its grubby hands off their Medicare, or when farmers can't even tell you how much they get in federal crop supports but keep electing know-nothings like Michelle Bachmann, entitlement has set in to a level that people consider structural. Removing such supports will not be a popular endeavor.