Not completing the equivalent of a high school education has significant economic and social implications in the U.S. and globally. When opportunity and information gaps between students are allowed to continue, the impact on dropout rates is considerable. School building leaders and school counselors can collaborate to encourage students' connection to their school community and education; lessening their likelihood of dropping out. This article explores evidence-based interventions delivered within a comprehensive school counseling program focused on engaging students in developing a career plan. A particular emphasis is on collaborative, proactive actions towards enhancing career development and reinforcing the message that "dropping out is not an option."