[anotheruser092]

Great film, but right after that, Sean (Robin Williams's character) says:

"It's not about the job. I don't care if you work for the government. But you can do anything you want, you are bound by nothing. What are you passionate about. What do you want? I mean there are guys who work their entire lives laying brick so that their kids have a chance at the opportunities you have here."

So, instead of praising Will, Sean questions why Will seems determined to keep drifting while seeming clever. I always thought the implication was that it's better to define yourself as "for" something than "against" something, even if you sound smart in a wicked way by doing so.