This dissertation investigates patterns of action and decision-making patterns by artists with cultural production industries. In particular, it explores how individuals navigate these uncertain, project-based fields, which are characterized by network forms of organization. Drawing from of five years of ethnographic research into stand-up comedians in Los Angeles, I crafted three chapters that examine participants’ decision-making and social organization. The first chapter covers the underlying processes and mechanisms for career development among artists. It introduces and defines the model of a layered career. In the case of stand-up comedy, individuals progressively move through three layers. Each exhibits its own distinctive organizational bases, challenges, interactional processes, relationship types, and rewards. While development involves one matriculating through layers, it also requires artists to maintain their participation in prior layers, because each is ideally suited for different aspects of practice, creativity, and social support. Careers in these contexts involve building a durable infrastructure rather than a simple passage through discrete statuses. The second chapter explores the informal enforcement of intellectual property rights in stand-up comedy. In particular, it focuses on inconsistent sanctioning of joke theft. I illustrate that enforcement is loosely coupled to the severity of a transgression and is more dependent to a comedian’s disharmonious status, especially the incompatibility between high commercial success and low peer esteem. Sanctions frequently emerge as a response to one’s history of boorish and disrespectful behavior or aloofness. The success of these claims, which heavily resemble scandal processes, depends on the reputations and statuses of relevant actors—particularly the accused transgressor, the moral entrepreneur behind them, and relevant third parties. The final chapter explains comedians’ high rates of persistence during middle and late-career stages, despite low and diminishing odds for stardom or optimal outcomes. I attribute this to this labor market assuming the form of a commitment trap. While most entrants have early exits, ambiguous feedback surrounding outcomes or prospects and the specificity of their investments lead aspirants to persist. Taken together, this dissertation illuminates core processes and mechanisms that apply to careers in cultural production industries and, in a larger sense, other forms of contingent employment.