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While life-course criminology has shown the importance of marriage, work, and military service for changing the patterns and trajectories of individual lives (Laub and Sampson, 2003), this paper focuses on education as a catalyst and turning point for individuals who are living within the confines of a maximum-security prison and who are willing to work to improve their life chances. Education, broadly defined, is an important avenue for redirecting life trajectories during imprisonment; this analysis shows how men serving lengthy sentences “make good” in prison (Maruna, 2001) by investing energy and sustained effort in the educational opportunities that exist within state correctional facilities. Participation in college classes, particularly, is analyzed as a turning point in the thinking and motivation of imprisoned men. While their life trajectories may be redirected yet again when faced with the myriad of challenges associated with reentry, prison education is an important addition to the toolkit of skills and assets that formerly incarcerated individuals carry with them back into the community.