Willy depends on influence, personality, and people liking him. The trouble is, old age has robbed him of these -- if he ever had them -- so he's living in a dream world. He idealizes the death of an 84-year-old salesman who died alone in a hotel room. He ignores the loneliness of such a death and exaggerates the importance of the man's funeral. He likes to think his own funeral will be a big one and lots of important people will come to it. The old man's death underlines the question, "What's it all for?" Why are we so concerned with material success and so unconcerned with the spiritual -- that is, happiness, meaning, and fulfillment?
Willy wants desperately for his son Biff to be a star. Success to Willy is the overnight kind, not the kind you build day-to-day, and he believes Biff can be a professional football player. He wants it so much and is so enamored with the possibility of a son who is a star that he ignores Biff's character flaws as he's growing up. He doesn't correct Biff when he steals a football, for example, and doesn't urge him to study so he can graduate from high school. Instead, he encourages Biff to rely on Charlie's son (Bernard) who studies hard and can give Biff the answers most of the time. At the same time he tells Biff not to be like Bernard because people who study hard are not well liked by others.
When Biff fails math and doesn't graduate, Willy blames the teacher. Charlie, by contrast, is not so wrapped up in what career his son will pursue. He lets Bernard find himself and what he wants to do with his life, and the result is that Bernard becomes a lawyer.
When Willy says to him, "And you never told him what to do, did you? You never took any interest in him," Charlie answers, "My salvation is that I never took any interest in anything." Here, Willy understates his obsession with Biff's success. He took more than an interest. He wanted to live his life through his son. Biff's stardom would bolster the self-image Willy longs for -- of a man who has made it, a big shot.
Willy's idea of success is based on money. Towards the end Willy says to Charlie, "Funny, y'know? After all the highways, and the trains, and the appointments, and the years, you end up worth more dead than alive." He's thinking of his $20,000 life insurance policy that would give Biff a new chance to make good. Charlie answers, "Willy, nobody's worth nothin' dead." Charlie values life more than money. Charlie's identity isn't all tied up in his son's accomplishments and doesn't require hitting the big time. Willy says to him (about Biff's career as a football player), "When this game is over, Charley, you'll be laughing out of the other side of your face. They'll be calling him another Red Grange. Twenty-five thousand a year." Charlie, unimpressed with money and fame, kids, "Who is Red Grange?"
It is significant that Willy, who believes so completely and aims so high, fails while Charlie, more realistic, succeeds. The American Dream encourages people to aim high. But there is actually only room for a very small percentage at the top. Willy lives in a dream world where anyone can become rich, while Charlie lives in the real world where it's more important to be happy and fulfilled. Willy loses everything because he can't give up his illusions. When Willy asks Charlie how his son "did it," Charlie gives the essence of his outlook. "He prepared himself." In other words, Bernard studied and day by day did the things he needed to do to obtain gainful and meaningful employment and in the end did well. The story makes the point that success is not a one time lucky event, but one must build on small successes over time. Although there are a few celebrities who do make it "overnight," they are not always happy and fulfilled by fame and fortune. Arthur Miller's wife Marilyn Monroe is an example of the American Dream gone wrong. So is Willy Loman.