Losing his mother at a young age is a pivotal event for Jimmy Herf, and he also loses his youth, his direction, and his passion. He grows up to spend his life in New York feeling lost and aimless. His close relationship with Lily before she dies borders on co-dependency, especially once she becomes ill. After Lily dies, Jimmy loses the purpose he had when she was alive. He has not had a typical childhood, so when he lives with his aunt, uncle, and cousins, but has no real connection with them. He is not used to being with other children and has formed a lively imagination as a result of spending so much time alone. While embarking on adulthood, he rejects the path he is expected to take and opts to get as far away from his past as possible, and this is exemplified by his choice to become a newspaper reporter. in doing so, Jimmy forsakes true financial success, which is the only type of success which his family values.  

Jimmy’s circle of friends, his work as a reporter, and the coming war all turn Jimmy further away from the bourgeois, capitalist lifestyle indicative of his family. He becomes more hardened against the rampant capitalism and empty materialism that he sees everywhere in the city and also more sympathetic to the working man. Still, even as he works at being a reporter, he never finds real success as a journalist and constantly dreams of leaving New York. Jimmy’s brief brush with happiness comes when he is away from New York and he and Ellen marry in Europe. Notably in Europe, Jimmy’s happiness results from the fact that he and Ellen are on equal footing. There is no financial or social discrepancy between the two as there would be while living in New York. But reality gets in when they return to the harsh city, and Jimmy can never hope to provide the kind of economic or social life to which Ellen is accustomed. He talks about leaving New York during his entire adult life, but it is the demise of his marriage to Ellen that pushes him to take the final steps to leave. Throughout the book, Jimmy’s happiness is dependent on his removal from New York, so when he leaves in the last pages there is a rare hope that Jimmy will finally be content with his life.