Dreams from my son

I'm too embarrassed to say what I considered being when I was a child my son's age, but I can safely say that such thoughts have made me feel it necessary to instill more worldly thoughts into my son's mindset.
Freakonomics would have me believe that my parenting methods will have very little influence over the man my son shall be. Regardless, I want my son to be better prepared for the things I never considered until having to make crucial decisions when the matters come up without warning. I was from a small town, so I had small town thoughts. I had a lot of weaknesses, and I took the road of least resistance more times than I'd like to admit. I was a kid. I was willfully ignorant by avoiding books and by being born before the internet existed in the everyday sense.
My son currently has First in Math as his homepage only because he completed all of the reading assignments from Raz-Kids. I take it for granted that he's gifted in math and reading, but I shouldn't given that he is a clean slate that needs to be steered towards being well rounded. He could be getting by on his great memory like I did, so I want to develop his critical thinking skills to ensure he doesn't simply "plug and chug" or "parrot" correct answers to coast through school into college.
Sure, my son can dream of being a pitcher, a writer or a physicist, but I don't want him to ever think he's limited in his options.