The current article explores the possible selves, or future expectations, of 543 incarcerated juvenile offenders in four Western states in the United States. We argue that juveniles who are able to articulate future expectations and fears and generate concrete strategies for achieving their goals have higher levels of motivational capital (i.e., resources which provide momentum for behavior) and thus greater readiness for transitioning back into society. We found that a majority of juveniles were able to articulate simple expectations about the future; however, less than a quarter recognized the relationship between hopes and fears and connected them to concrete strategies. Findings did not differ significantly according to race or gender. We point to a need for juvenile corrections to work with all youth to construct plausible reentry plans. Furthermore, we suggest that research is needed to compare postincarceration success of youth with varying levels of motivational capital. (Contains 3 tables.)