Many of Holden Caulfield's issues directly stem from the tragic death of his younger brother Allie, who passed away when Holden was thirteen years old. Holden has never properly coped with Allie's death and seems to suffer from post-traumatic stress disorder connected to the tragic incident.

One of Holden's main struggles in the story concerns his inability to move on with his life by making peace with his past. Holden desperately fears becoming an adult, believes that the competitive world of grown-ups is full of "phonies," and desires to remain an adolescent. His fear of the future causes him to stagnate, and he naively wishes to save children from entering adulthood by becoming a "catcher in the rye."

Holden also has identity issues and lacks self-awareness. Holden desires to be a suave, charming individual but does not possess any of the desirable traits that he resents in his charismatic roommate, Stradlater. Holden also struggles with his sexuality and social skills. His immaturity, lack of impulse control, and narrow perspective negatively influence his personal relationships with others, and he is unable to engage in meaningful, engaging social interactions. Despite his desire to connect, he comes across as annoying, offensive, and ignorant in many conversations, and he can't interact with the people who genuinely care about him the most. Instead of meeting up with Jane Gallagher, for instance, Holden seeks comfort from people like Sally Hayes or Carl Luce.

Holden struggles to deal with survivor's guilt after his brother Allie dies. This crisis of a sibling death leads him to become profoundly alienated from the life of his school, his studies, and his peers.

Holden struggles with a preoccupying urge to protect those whom he perceives as young and innocent, such as his sister, Phoebe, as well as children in the world in general. He wants to protect them as he couldn't protect Allie. He dreams of becoming the catcher in the rye, a fairy-tale type figure who catches children who are ready to fall over the edge of a cliff.

Holden struggles to come to terms with who he is and with the fact that he can't save the world. He struggles, like many teenagers, to find authenticity among people who often seem phony and caught up in false values.

Holden is a sensitive person: he worries about his friend Jane, about Phoebe, and about the nuns he meets while breakfasting in a diner, noting that they eat far less than he does. He hires a prostitute but only to talk to her. While he has to deal with a world filled with much egotism and unkindness, he manages not to lose his basic decency, and in the end, he realizes that he has to trust that Phoebe will be OK. We are left hoping that despite a mental breakdown, he will find his path through life.

Throughout The Catcher in the Rye, Holden Caulfield seems to struggle with many aspects of his life. At the beginning of the novel, he is temporarily suspended for his poor academic efforts. As he appears before Mr. Spencer, he is embarrassed at his tremendous lack of effort on a particular essay on the Ancient Egyptians. Due to his own cynicism and inability to get along with others, Holden finds himself having a tremendously difficult time applying himself to school.

As the novel continues, Holden wanders around New York, looking for some meaning. Needless to say, he has great difficulty finding it, for most of the people he encounters he considers to be phony. Whether its the older women he encounters in the hotel, the young prostitute (and her pimp), Jane Gallagher, or his old English teacher Mr. Antolini, Holden can't quite seem to connect to others. He mourns the death of his brother Allie, and it's not until he spends time with his younger sister Phoebe that he begins to feel any sense of happiness and optimism.

Holden struggles in several different areas throughout the novel. Externally, Holden struggles with his school work. He is failing every class except English at Pency, which is why he is not allowed back for the next term. Holden also has a litany of social problems. He struggles to maintain genuine friendships with other boys his age and is often highly critical of those around him. Holden portrays his hypocritical nature by continually insulting and criticizing his acquaintances while refusing to analyze his own behavior. Holden also struggles to develop relationships with women throughout the novel. He lacks the ability to communicate with Jane Gallagher and does not express empathy towards Sally Hayes. Holden's struggles can be attributed to the loss of his younger brother Allie. Since Allie's death, Holden has struggled to move on with his life. He cannot come to terms with his future and instead lives in the idyllic past when Allie was alive. Holden's fear of becoming an adult comes from his inability to move on after Allie's death. His phycological issues negatively affect his relationships, perspective, and attitude throughout the novel.

Holden struggles are with relationships, both with people and with himself. When we look at other people, the struggle with relationships is evident through his interactions with his roommate when he says he is going on a date with Jane Gallagher. 

"Jane Gallagher. Jesus. I couldn’t get her off my mind. I really couldn’t. I oughta go down and say hello to her, at least.”

Holden has a clear interest in Jane, but he cannot bring himself to go down and say hello to her. Throughout the rest of the story his interest in Jane is clear, yet he cannot bring himself to ever call her.

He also struggles with family and class expectations. Growing up in an upper-middle class family, both his family and his economic class expect him to succeed at a prestigious prep school and then go on to attend an ivy league college. This scares Holden so he plans spontaneous fantasies that will not work, like running away with Sally (which scares her) and running west to live with a deaf mute.