Willy Loman is an adult and so to a very large extent responsible for the failure of his dreams. He bought into the wrong dream—the American dream—of sitting back and reaping the harvest of easy money as a salesman in the land of opportunity. He believed too wholly and uncritically in such ideas as the following: it is not what you know but who you know that counts, personality matters more than knowledge or character (Willy has an affair that devastates Biff when he finds out about it) and you get can ahead without working hard. None of this works out for Willy, and yet the dream has been a part of his life for so long that he can't abandon it, no matter how many times it fails him. It has become an addiction for him; like a gambling addict, for a long time he believes that the next roll of the dice will put him on easy street.

Willy would have been better off to follow his heart and pursue his true talent at gardening. It might not have had the allure of a big money career, but he would likely have been more successful at it and more fulfilled.

Willie Loman has no one but himself to blame for his failure to achieve his dreams. Although he has had difficulties in his life that make it hard for him to get ahead, his own character flaws ultimately cause his dreams to disappear. One of the major factors that worked against him was his lack of a father's direction. Willie's father left when he was a baby, and because of the he still feels "kind of temporary about myself." That is a difficult obstacle to overcome, yet many people have grown up fatherless and have been able to achieve their dreams. Another obstacle to Willie's success was the prevalence of enablers in his life. His wife, Linda, never confronts him on his inappropriate behaviors or his lies. She always tries to encourage him, but she doesn't respect him enough to present the truth to him about himself. Even Biff, who becomes furious at his father because of his adultery, never confronts him about it but handles it by becoming passive aggressive towards Willy. And Charley, while seeming to speak frankly to Willy, continues to pass money to him without demanding that Willy look at life realistically. While these people enable Willy's bad behavior, they cannot be held responsible for it. 

Willy's personal character flaws are what prevent him from achieving his dream. First, he has a desire to get by on personality without providing value by making meaningful contributions to the world. The reason he chooses to stay working as a salesman is that he has the picture of the 84-year-old salesman who was able to make a living just by calling people on the phone--a life of ease, as Willy sees it. His whole goal was to succeed in life without paying his dues. This is consistent with his habit of stealing, such as stealing from the construction site next door to build his steps. That example passed on to his sons in that neither wants to work hard, and Biff, in particular, steals. His dishonesty with himself and others is the biggest obstacle to his success. He lies to his wife constantly, even cheats on her, and continually lies to himself about his abilities and earnings. A salesman who is perceived as dishonest is unlikely to do well with customers. Because Willy never confronts the reality of his life and his own shortcomings, "he never trained himself for anything," which Bernard suggests is the reason for Biff's failures, but also applies to Willy.

Although Willy's lack of a father and his many enablers complicate his road to success, the real factor that prevents him from achieving his dreams is his own flawed character.