Research shows that certain work roles constrain labor market success when individuals transition to new work roles, as they are viewed as discrediting by potential role partners. However, workers increasingly hold multiple roles simultaneously, which may alter the inferences drawn from roles that are discrediting in isolation. Building on role accumulation theory, we theorize that work roles that are net liabilities in isolation, such as the entrepreneur role, can become net assets as part of a compensatory role set, and we identify a new theoretical mechanism of role rectification through which this effect occurs. Mobilizing verbal protocol, experimental, and archival data sources, we find evidence for role rectification using the case of hybrid entrepreneurs, but we also find that the benefits of role rectification are attenuated in contexts where role accumulation magnifies role nonconformity risks.