While Willy and Linda are talking downstairs, Biff and his brother Happy listen from the loft where they sleep. The two grown men discuss their past failures. Biff says that he can't find a job that both pays well and is satisfying, while Happy similarly admits that he doesn't like his job as a business clerk. Both brothers day-dream for a time about going out west and making a living together on a cattle ranch. "Men built like we are should be working out in the open," Biff asserts.
Happy too, but Biff especially, feels guilty that he's not lived up to his father's expectations. "I'm thirty-four years old, I oughta be makin' my future. That's when I come running home. And now, I get here, and I don't know what to do with myself. I've always made a point of not wasting my life, and every time I come back here I know that all I've done is to waste my life," the older brother admits.
Though Happy initially seems to agree with Biff's sentiments that money-grubbing isn't what life is all about, the younger brother later contradicts himself when he reveals his desire to emulate his rich boss. He asserts, "when he walks into the store the waves part in front of him." Happy goes on to brag about his sexual encounters with various women, including his bosses' fiances. Yet even this doesn't satisfy him. Later, the reader will learn that Happy takes after his father in this regard. The conversation ends with a reference to Bill Oliver, an employer of Biff in the past. Biff hopes that this businessman will lend him a few thousand dollars to buy his ranch out west.
Soon they hear Willy from downstairs, talking to himself as usual. He's actually speaking to Biff-the Biff of ten or more years ago. This is one of the first signs that Willy is living in the past.