The significance of Duddy’s recurring dream lies in the fact that Duddy is solely focused on his conscious dreams of achieving land, land that he believes will make him somebody. Duddy continually skirts the line between right and wrong in his pursuit of “fame and fortune,” and his recurring dreams focus on his subconscious fears, fears which indicate both a subconscious idea that he is using the wrong methods in his quest for monetary gain and fears that either he will either never be able to achieve his goals, or they will be snatched out of his hands once he finally does achieve them.
Duddy is also haunted by guilt for the various things he has done wrong in his life, such as the prank calls he made that inadvertently led to the death of John Macpherson’s wife. In his chaotic world where his father continually dances around moral boundaries, such as being a pimp on the side, Duddy turns to his grandfather, Simcha, for a role model. It is Simcha’s advice that “a man without land is nobody” that stirs up the overwhelming desire in Duddy to acquire land. Thus, he believes that it is solely through the achievement of certain material goals that he can gain the respect and love of his family, including his grandfather. He does not seem to understand the old adage about “ill-gotten gains” and carelessly walks over the people in his life who attempt to help him in his pursuits, ultimately committing more acts for which he feels guilty, such as stealing from his disabled friend, Virgil.
His inward guilt continues to grow, and despite the fact that he seems to have achieved the respect of his father, who does not seem to care what morals have been cast aside, he has ultimately lost any chance of respect for the one whose opinion meant the most to him—Simcha, his grandfather. And though he can manage to push aside his deeds during the day, he continues to be haunted at night by the wrongs he has done to achieve his ambitious dreams and by the fears that the consequences of those wrongs will cause his dreams to be taken away from him.