The great postwar buildout comprises the most dramatic chapter in the longer history of suburbanization in the US. No other moment compares in terms of scale, speed, or social significance: the period saw a broader white middle-class identity coalesce around suburban homeownership. The literature that attends to these physical and social transformations – narrative material that continues to shape perceptions of suburban life today, and that provides this chapter with its principal focus – is characterized by hyperbolic tensions about money. Concerns about not having quite enough of it repeatedly become matters of life and death in these stories; the very real advantages of suburban living are thus typically obscured or disavowed. This chapter argues, however, that some of the period’s literature possesses a further, instructional role: texts such as Sloan Wilson’s 1955 novel The Man in the Gray Flannel Suit offer guidance, in a manner not unlike contemporary self-help literature, about how to make money matter to just the right degree to maximize the advantages of suburban settlement. This fine balancing, which is always executed in the absence of any consideration of the precarity of others, is a precise measure of the privilege of these fictional white middle-class subjects.