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BIFF: Well, I spent six or seven years after high school trying to work myself up. Shipping clerk, salesman, business of one kind or another. And it’s a measly manner of existence. To get on that subway on the hot mornings in summer. To devote your whole life to keeping stock, or making phone calls, or selling or buying. To suffer fifty weeks of the year for the sake of a two week vacation, when all you really desire is to be outdoors with your shirt off. And always to have to get ahead of the next fella. And still—that’s how you build a future. (Act 1)
Biff struggles with the competition inherent in the American way, but still holds it as a truth that he must take a path unpleasant for him in order to succeed. It seems that he longs for a life that's more simple – a working class lifestyle that his father sees as beneath him. Interestingly, though, throughout the play Willy seems to long for simpler things as well, like growing things.
WILLY: That is a one million dollar idea.
BIFF: I’m in great shape as far as that’s concerned!
HAPPY: And the beauty of it is, Biff, it wouldn’t be like a business. We’d be out playin’ ball again…
BIFF [enthused]: Yeah, that’s…
WILLY: Million-dollar! (Act 1)
While Biff and Happy are interested in finding work that is tolerable, Willy is fixated on ensuring that the boys find a lucrative profession likely to lead them down the path to success and greatness. Is Willy so bad for wanting this? Are Biff and Happy so bad for wanting to be… happy?
BIFF: He walked away. I saw him for one minute. I got so mad I could’ve torn the walls down! How the hell did I ever get the idea I was a salesman there? I even believed myself that I’d been a salesman for him! And then he gave me one look and—I realized what a ridiculous lie my whole life has been. We’ve been talking in a dream for fifteen years. I was a shipping clerk. (Act 2)
Biff points out that because of excessive dreaming and fantasizing about a better future, he had lost his grounding in reality. When he forces his father to face this reality, it leads to Willy's destruction.