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A negative spiral of joblessness and crime/incarceration suggests that employment states between pre- and post-incarceration mutually constitute one unit of trajectory, including incarceration periods in between the two phases. Previous research is often divided into two separate phases of the life course, either the pre-incarceration or the post-incarceration phase, with little attention to how the two phases are related each other. Furthermore, previous research focusing on the negative spiral between unsuccessful employment states and incarceration hides potential heterogeneity of labor market trajectories of the ever-incarcerated population. Using the holistic approach of Sequence Analysis, I explore the employment trajectories of the ever-incarcerated population from the National Longitudinal Survey of Youth 1997 cohort sample. I find that there is significant heterogeneity resulting in five distinct trajectory patterns: unstable employment, early exit from the survey, prisoner career, withdrawn from the labor force, and stable employment, and that the patterns are stratified by race.