I find characters who are at cross-purposes with society, or opposed to society in some way, interesting because they are by definition the underdogs. They have to be clever, cunning, imaginative, dogged, and wily--whereas society merely has to lean its weight a little.
F. Scott Fitzgerald was both a perfect and terrible fit for Hollywood. His youthful fame gave him a shrewd perspective on that shallow, tinselly world. Yet while working there in the last three years of his life, he was a sad case: a debt-ridden genius, alcoholic, selling himself to collaborate on second-rate screenplays.
I think aspiring writers need as much discouragement as we can muster. Nobody should undertake the life of a fiction writer--so unrenumerative, so maddeningly beset by career vagaries--who has any other choice in the matter. Learn a trade! Flannery O'Conner said it best: "People are always asking me if the university stifles writers. I reply that it hasn't stifled enough of them."