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Employment anchors many post-conviction experiences, offering practical benefits vital to long-term success and also plays an integral role in contributing to individuals’ sense of self. The current study examines post-conviction employment experiences, particularly as they relate to pre-conviction circumstances. Drawing upon semi-structured interviews with individuals following a felony conviction, experiences within employment, the meaning or impact perceived, and reflections on future pursuits are explored. Findings indicate a tremendous amount of variation in employment type, shifts, and value, with many hoping for more personally fulfilling employment opportunities in the future. This did not diminish the practical value or import of current employment but instead reconsiders the quality or value of employment as a potential avenue for intervention and building toward the future.