“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.” 

When Biff returns home from Texas, he shares his woes about the capitalist work ethic required by the American Dream. The endless number of workweeks grants no more than two weeks of vacation, which doesn’t suit his desire to be in the outdoors. He expresses his true inclination towards working with his hands in the outdoors, contrary to Willy’s expectations of him. 

“I’ve always made a point of not wasting my life, and everytime I come back here I know that all I’ve done is to waste my life.” 

Normally, Biff believes that his choice to work in the outdoors gives his life meaning. However, he is always reminded of his failures in the eyes of his father and in respect to the American Dream upon returning home. Willy’s expectations of Biff leave him in an impossible position, forced to concoct ways to start a successful business from scratch despite having no capital or viable partners.

“I don’t know what the hell I’m workin’ for. Sometimes I sit in my apartment—all alone. And I think of the rent I’m paying. But then, it’s what I always wanted. My own apartment, a car, and plenty of women. And still, goddammit, I’m lonely.” 

Conversing with his elder brother Biff, Happy admits that though he has everything he has ever dreamed of and is well on the path to the American Dream, he is unbearably lonely. Though he is working hard for what he always wanted, he doesn’t see a purpose in his struggle. This highlights the emotional hollowness at the center of the American Dream.