Wolff’s memoir frequently explores class mobility and social status from the perspective of an outsider looking in, which ties into the theme of institutional and social norms and conventions. He is expelled from a prestigious prep school that he was only able to afford on scholarship (in part because he forged his credentials). After joining the military, he finagles his way into a role in the Special Forces and as an officer by presenting a firm disposition, despite struggling in his duties. While in language school, he dates Vera, the upper-class descendent of Russian aristocracy, and meets Pete Landon, a well-to-do, highly educated Foreign Service Officer. Ultimately, Wolff ends up at Oxford, yet another bastion of the well-off. It is worth mentioning that the nature of a con man like his father is to attempt to con their way into a richer lifestyle, one they cannot truly afford and one to which they do not truly belong.

However, the memoir deals with status largely from a perspective of disillusionment. For example, while Vera is from an aristocratic family, it is a deeply troubled one between her own outbursts and her brother’s refusal to leave his room over a minor incident.