I feel really lucky that my 11th grade American literature teacher devised a curriculum that relentlessly attacked the American success myth.
We read Christopher Lasch, Ben Franklin's autobiography, The Great Gatsby, "Paul's Case" by Willa Cather, a bunch of other stuff ....
And at the same time, I was volunteering with the local hippies, and my mentor was a guy who'd burned out on working as a philosophy professor, and now did carpentry to support his peace activism.