Eeek, trinaward - eek. My headcanon for Dean is HUGE - uhmmm...

Dean isn't entirely sure what he wants out of life. As much as hunting has ruined any chance of a 'normal' existence, even given the option/AU life, he's the kinda person who would make a success out of just about anything. But like most folk who are smart and good at a lot of things, he struggles to focus. But give him direction, and watch him fly :)