Willy Loman's dream was to become a well-liked, wealthy salesman like Dave Singleman, who was conducting business from his hotel room at the age of eighty-four and died a popular man. Willy was inspired by Dave Singleman to pursue a career as a salesman and naively believed that he could attain popularity and wealth with relative ease. Willy also has a warped perception of the American Dream and believes that being well-liked is the key to success. He completely neglects the importance of hard work, dedication, patience, and opportunity in order to attain wealth and ascend the social ladder. Willy's dream of living a fulfilled, content life as a salesman is wrong for him on many levels. Willy is depicted as an excellent handyman, who is talented and creative with tools in his hands. In addition to being a natural builder, Willy also has an affinity for the outdoors and enjoys being outside. He feels cramped and stifled in the city and desires to travel to Alaska, where he can enjoy the outdoors. Willy would have been better suited to enter the field of construction or choose an outdoor occupation instead of becoming a traveling salesman. Tragically, Willy fails to become a successful salesman, experiences auditory and visual hallucinations, and ends up committing suicide.

The dream that would have made Willy happy is to have followed his inner love for building and creating things. It would have been a gift that kept on giving, since it would have given him both the pleasure and the benefit of being productive in society, and to be there for his children.

Instead, Willy's dream was to follow the steps of another man. When  he was little, a man named Dave Singleman. This man was the inspiration behind Willy's career choice. He saw how this man supposedly made lots of money out of a hotel room. He figured he could do the same, and have a good lifestyle just on the basis of "being liked" and achieve financial success.

However, when Biff talks about a "wrong dream" he is mostly referring to the fact that his father was following another man's dream. He never once stopped to figure his own destiny and, instead, went following a journey already walked by another person.