My mom and dad both did their undergrad at big state schools (different states) and went on to do cool but completely academically unrelated things. My aunt and uncle, with whom I'm quite close, are both humanities PhDs who have worked as professors and my aunt moved into administration as a dean, president, and then chancellor. They're the ones in my family who have the post-undergrad experience and have been my best source of information, despite coming from a different field. I didn't grow up around academia, though, so I have a little of both worlds, I guess.
I guess all of OUR kids will be of the "parents have PhD" type, though, huh?