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While agency is increasingly recognized as critical to the desistance process, the manner in which individuals elect to exercise their agency and the barriers they face may influence desistance outcomes. Following up on a cross-sectional analysis of actions undertaken by individuals under community supervision to improve their lives, the objective of the present study was to evaluate the status of these life betterment projects six months later. Gender and race comparisons of interviews from 233 people supervised on parole or probation revealed that the success of life betterment projects was dependent on the nature of the project, as well as the presence or absence of structural barriers. Theoretical and practical implications relating to desistance are discussed.