Willy's greatest fear is his fear of failure. This is supported by the way Miller depicts Willy's worldview, as well as his relationship with Biff.
In Death of a Salesman, success and failure are closely linked together. Success is the lens through which Willy views the world. This is depicted through the story of his brother Ben, a man who is "success incarnate". Ben is who Willy could have been had he chose to follow his brother instead of becoming a salesman. Ben "started with the clothes on his back and ended up with diamond mines" because he dared to walk "into the jungle". For Willy, what matters is the end result (success), not the journey. His superficial understanding of the world brings light to Miller's criticism of the American Dream. After all, even Ben admits that instead of going to Alaska, he ended up in Africa, which Willy does not question. Blinded by his desire for success, Willy never plans ahead. He is a prisoner of his delusions.
However, failure in the play is never far from the dream of becoming successful. Willy's relationship with Biff highlights the contrast between both characters' life perspectives. As Biff realizes and comes to terms that he is, according to his father's criteria, a failure and will never live up to his expectations, Willy slips more and more into insanity.The most significant quote that summarizes their chaotic connection is from Act II, when Biff tells his father that he is "a dime a dozen, and so are you!" Interestingly, Willy answers that he is not a dime a dozen, but Willy Loman.
The use of the idiom is very meaningful. Of course, by "dime a dozen", Biff means that neither he nor Willy are special. But it also relates to money, which, in the play, defines success. Willy's answer shows that behind his fear of failure, of being a nobody just like everybody else, hides a lack of identity. Who is really Willy Loman? Instead of describing what makes him special and not a "dime a dozen" like Biff asserts, he defines himself by his name, which is meaningless.
As the play moves forward, the barriers between past and present, reality and dream become more and more blurred. Characters from the past invite themselves into the present and the walls of the house the story is taking place in disappear. Willy's sanity hinges on the life he created for himself, which turns out to be based on lies. When it becomes clear that, far from being well-liked, when his belongings keep breaking down, Willy decides to kill himself because he is unable to cope with the truth.
Willy Loman seems to have three primary fears in the play. He fears failure; he fears that Biff will reveal Willy's affair to Linda; and he fears that he will have nothing to leave his sons, especially Biff.
Willy defines success as being liked. Although he wants financial success, he is convinced that the way to become a top salesman is to be well liked, and he believes that he can become as wealthy as a salesman as Ben did in exploring the continent of Africa. At the beginning of the play, Willy's insecurities are very apparent as he confides in Linda that people don't laugh at his jokes and think he's fat. Charley asks Willy why he's so obsessed with being liked. The best explanation of that obsession is the story Willy tells of the eighty-four-year-old salesman who was able to rake in orders by phone in his old age—the man who died the death of a salesman, attended by adoring customers from several states.
The reason there is so much tension when Biff comes home is that Willy fears that Biff will reveal Willy's affair to Linda. Willy misses Biff when he's away, but when Biff writes and says he's coming home, Willy becomes increasingly disturbed. Linda begs Biff to reveal what the tension between him and his father is, but Biff won't say anything about the "other woman" he met when he surprised Willy in his hotel room on a business trip. Near the end of act 2, Biff speaks with Willy while he is planting seeds and tries to get him to go into the house to speak to Linda. Biff just wants to tell Linda and Willy the truth about his meeting with Bill Oliver and to say that he's leaving for good, but Willy must assume Biff intends to tell Linda about Willy's infidelity. When Biff tries to pull Willy inside, Willy "becomes frozen, immobile" and speaks "with guilt in his voice," saying, "No, I don't want to see her."
Finally, it's clear that Willy fears dying without leaving a proper legacy for his sons. He states in a relived (or possibly imaginary) conversation with Ben, his brother, "Sometimes I'm afraid that I'm not teaching them the right kind of—Ben, how should I teach them?" This shows his fear that he's not raising his sons properly. Since his own father abandoned him, he has no role model for how to raise a family, so he fears he's doing it wrong. Later, again in an imaginary conversation with Ben, as Willy shares his plans to kill himself for the life insurance proceeds, he asks, "Why can't I give him something and not have him hate me?" He has previously worried that he'll leave nothing to his family.
Of these three fears—failure, having Linda learn of his affair, and not leaving his sons a legacy—the last one is probably Willy's biggest fear. It is the one that drives him to commit suicide.
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