Willy's need to be well liked most likely stems from his abandonment issues with his father and brother. Ben describes his father as a masculine man who was skilled with his hands and had an entrepreneurial spirit. According to Ben, Willy's father was a successful salesman who produced what he sold. We see Willy's fear of abandonment in his memory of Ben's visit. When Ben says he must leave to catch a train, Willy frantically searches for ways to delay his departure. He shows off his children to Ben in a desperate plea for approval. With his father and Ben gone, Willy is unable to develop a normal concept of self worth. Therefore, he models that self worth after the American dream which is highly unrealistic. He ends up downplaying more important measures such as family love and support, and the freedom to choose what to do with your life. It becomes fairly clear that Willy made a poor choice in becoming a salesman after we see his dream of living in the Alaskan woods which related to the American dream of living life on the frontier. The image of the American pioneer who searched for riches began to change in the late 1940s as people realized that the real place to strike it rich was through capitalism and consumerism. Business entrepreneurs replaced the explorers of the old west. Ben represents a character that was actually able to get rich by literally searching for riches in the wilderness of an African Jungle. In the end of the book, Willy may be alluding to the fact that he regrets becoming a salesman when he uses gardening as a metaphor for his legacy. Just as Biff had enjoyed his time working on a ranch, it seems that Willy preferred working in a more natural environment.
Willy's thought processing ability is marred by a lifetime of him creating his own realities to conceal his own failures in achieving his dreams. His delusions are often revealed in the contradictions that arise from his multiple mindsets. For example, he refers to his car as a piece of trash at one point and then claims that it is "the finest car ever built." He says that Biff is a lazy bum in one instance, and later says that he is anything but lazy. Willy acts as an enabler to Biff's compulsive thievery which later becomes a crippling habit. He never reprimands Biff for his bad grades or the stealing and even laughs when Biff first steals the football and is impressed with his ability to get away with theft. It is possible that Willy doesn't reprimand Biff because he fears damaging Biff's ego or that he fears that Biff will no longer like him.
At the beginning of the play, Biff and Happy have come back home and are currently sharing their old room. Biff is the oldest son who was a football star in high school with several scholarships, but for the last fourteen years he has been unable to find himself and he has lost a great deal of his confidence. He is a war veteran and has had six or seven jobs since his time in the war (including one job as a worker on a ranch which he enjoyed). He taught his younger brother about women although he has no idea how to act around them. Biff is in a cycle of going home every time that he gets fed up with a job and then leaving home because of a fight with his father. He recently returned from somewhere in the West because his mother asked him to see his father. Biff and Happy went to school with Charlie's son, Bernard, who is now a prominent, successful lawyer. Happy works in a department store and has his own apartment in different part of New York. Willy has clearly favored Biff over Happy during their childhood because Biff represented a potential for the American dream with his reputation as a football star and his various scholarship offers. Happy began to emulate the high school Biff in an attempt to get his father's approval. Willy would praise Biff's success with women and his ability to get away with theft. As a result, Happy competed with more successful men by sleeping with their women as a form of theft that also established his sexual dominance.