What are the hurdles or obstacles in Holden's way?

Holden Caulfield encounters numerous hurdles and obstacles as he transitions into becoming an adult. Holden's traumatic experiences as a child have left him jaded, insecure, and anxious about entering the world of adults. Holden has not excelled academically and has flunked out of several prep schools as a teenager. His failing grades will negatively impact his ability to find a fulfilling job that aligns with his interests. His lack of enthusiasm for education has resulted in his expulsion, which will adversely affect his relationship with his parents. Holden's immaturity and awkwardness also present various hurdles and obstacles. Holden's inability to appropriately communicate with others results in his isolation. Holden confides in the wrong people and fails to make genuine friends with the other boys at school. He also struggles to express his emotions appropriately and has intimacy issues. Holden fails to have a genuine encounter with Jane Gallagher and instead takes Sally Hayes on a date. Holden's negative view of society, in general, will present numerous obstacles. Holden cannot stand superficial individuals and does not take advice very well. His bad attitude will not help him in the future, and Holden is doomed to repeat the same mistakes if he does not take advice from those trying to help him. Holden's skewed perception of the world presents the biggest hurdle and obstacle in his life. He is in desperate need of therapy and counseling in order to deal with his traumatic past and move forward in life with a positive outlook.