I think that much regarding the issue of failure is seen in Holden. A strong argument can be made that Holden's entire being is one predicated upon failure. There is little that Holden does which isn't failure. His time at formal schooling can be seen as one mammoth exercise in failure. He has talent, as Mr. Antolini indicates. Yet, Holden does not exercise it. Whether his refusal to do so is grounded in solid reality can be debated, but Holden's consistent and pervasive sense of academic failure is a part of his characterization and permeates the narrative.
Holden's interpersonal failure is another domain in which futility results. Throughout the narrative, Holden is unable to sustain much in way of personal relationships. Outside of his connection with Phoebe, there is much failure in how Holden interacts with people. He has few alliances, seen in his contempt and pity for Ackley and his oppositional relationship with Stradlater. The fact that Stradlater is perceived to be able to do what Holden cannot is another example of how failure is intrinsic to Holden. Sexual failure is another dimension to this, as seen with Holden's inability to sustain anything of note with Sally. Holden's failure in this domain is continued with Faith's rebuffing him, and his experience with the prostitute. The "fizzling out" with the Seattle girls is another instance of where failure is evident in the realm of sexual interaction. For Holden, there is a sense of failure in his interpersonal relationships. Whether this is his fault or the condition of the world around him is secondary to the failure that is present in his being with others.