This dissertation investigates the role of class and culture in the transformation of the labor process, employment relations, and labor markets of the trucking industry after deregulation. In recent years, trucking companies, who prefer to employ owner-operators because they are cheaper to use than company drivers, have increased truckers‘ opportunities to own their trucks and work as independent contractors. Using more than 120 interviews with truck drivers, managers, and owners of small and large companies, and secondary quantitative sources, this dissertation explains why some truckers choose to buy their own trucks while others reject such a decision as foolhardy and risky. I demonstrate that organization of the labor process and explicit conceptual framing by companies creates a worldview that determines how new truckers understand trucking leads inexperienced truckers to buy their own truck. The dissertation addresses several fundamental questions about economic transformations and class relations. Most importantly, the dissertation argues that accounts of class identity have misrepresented the stability of class identification by emphasizing how it is rooted in life-long processes of socialization. This dissertation demonstrates that class identification and beliefs about employment and market relations are remarkably malleable and can be rooted primarily in immediate workplace experience. In doing so it highlights the important but underappreciated cultural influence of class relations in the workplace on labor market decisions and the ability of class actors to shape economic systems more generally (e.g. employer-labor relations in a deregulated trucking industry).