In this study, regression analyses were conducted to ascertain predictors of employment-specific confidence and motivation of youth participating in a summer employment program. The study’s findings indicated that participants’ perceptions of several programmatic features, including their level of preparedness emanating from the program’s pre-employment session, were associated with greater confidence and motivation. Furthermore, male participants reported higher levels of employment-specific confidence than did the female participants, thus suggesting the need for programmatic changes. The implications of the study are considered in light of a new policy paradigm that emphasizes investing in education and skills training, particularly for youth.