In an apartment building on Chicago's Southside, fifty of the seventy-five residents are sex workers. Our study uses in-depth interviews and participant observation of Chicago's sex work economy to argue that sex work is one constituent part of an overall low-wage, off-the-books economy of resource exchange among individuals in a bounded geographic setting. To an outsider, the decision to be a sex worker seems irrational; in this article we argue that specific localized conditions invert this decision and render it entirely rational. For the men and women in our study, sex work acts as a short-term solution that “satisfices” the demands of persistent poverty and instability, and it provides a meaningful option in the quest for a job that provides autonomy and personal fulfillment.