In this article, the author explores the significance of “exits” for juvenile maleo ffenders who are preparing to leave correctional institutions. The analysis focuses on practical and cognitive exit strategies, anticipated challenges, and future visions based on qualitative interviews with 20 juvenile males (ages 15-17 years) from two correctional facilities in the upper Midwest region of the United States. At the juncture of exit, all of the youth were involved in practical preparation for reentry and shared an emphasis on the theme of “individual responsibility” for their futures. However, the cognitive strategies they used to prepare for exit were strongly differentiated by level of motivation or expressed “openness” to change. Youth who had little motivation to change tended to deny the potential challenges associated with their return to the community, whereas those who expressed a greater openness to change were contemplating how to achieve an alternative, law-abiding future while realistically considering the potential pitfalls of crime temptations. Ambivalence about change was the most common pattern, expressed as a desire to move toward desistance but lacking the internal confidence or sense of social support to achieve such change. From these findings, implications for theory and practice are proposed.