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This paper examines “doubling up,” a phenomenon in which individuals involved in income-generating crime also hold legal employment. Through life-history interviews with 100 formerly incarcerated men, we identified 44 individuals who engaged in doubling up. We explore three patterns: “breaking bad” (transitioning from legal work to doubling up), “breaking good” (transitioning from crime-only to doubling up en route to desistance), and “career doubling” (long-term engagement in both legal work and crime). Our findings contribute to the literature on work and crime by bridging rational choice and life course perspectives. We demonstrate that “breaking bad” decisions, while influenced by risk-reward calculations, are embedded in negative moral judgments of crime and affective attachments to work. Analysis of “breaking good” experiences supports Paternoster and Bushway’s (2009) desistance theory, while highlighting a new distinction between the initial decision to change and the decision to stop offending. The discovery of “career doubling” challenges existing assumptions about the relationship between work and crime. These individuals maintain long-term commitments to both legal and illegal activities, driven by “survival” motivations (managing the risks of crime) and “growth” motivations (enjoyment of work, pride in skills, and desire for legitimacy). This finding suggests that criminological theories need to incorporate a deeper understanding of the sociology of work and the complexities of managing multiple identities. Career doubling also highlights potential confounding effects in work-crime research, where a subset of individuals may not experience a deterrent effect of employment on crime.