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The examination of employment as a pivotal factor in shaping criminal trajectories has been the subject of extensive scholarly attention. However, despite significant inquiry, several questions remain underexplored, particularly questions about when and for whom employment works as a turning point toward conventionality. Specifically, this study seeks to advance existing scholarship by contributing to increasing efforts to capture the nuanced heterogeneity underlying the binary classification of employment status. It aims to incorporate a more comprehensive spectrum of employment characteristics—such as job quality, satisfaction, and income—and to investigate the differential impacts of employment on crime, with particular attention to variations across gender dimensions. In order to address these questions, I use the National Longitudinal Survey of Youth 1997 (NLSY97). The results can illuminate pathways for future inquiry into the mechanisms and factors that underpin variations in the influence of employment on distinct groups.