Dons a sort of sisyphean character, happier trying to get somewhere than he is once he has it. He wanted the the perfect American family, house in the suburbs, white picket fence, etc He got it and ruined it because he wasn't happy. He wanted to be a big wig ad man, he became a partner in a company he founded, won awards, had a great reputation within the industry then he ruined all that through his drinking because he wasn't happy. Ads sell people dreams, Don is the best at selling those dreams, not just to the public but to himself. Much like his target consumers the reality never lives up to the dream they are selling. Thats my general thesis on Mad Man so far. I suspect it'll also end this way, with Dons current dream of just being a creative, doing great like he was when he was young. But isn't desperately wanting to be where you were in your youth a midlife crisis? I'm expecting a massive breakdown next (half) season.
Wonder will Dick Whitman catch up with him.