The school dropout rate in America is too high, especially for low-income students and those from nondominant racial or ethnic groups. For many students, the social-psychological and behavioral disengagement from school that leads to dropping out often begins in middle school. Research on early adolescents confirms that increasing the perceived future career relevance of schooling is associated with higher levels of student engagement. This article describes the value of promoting future career relevance in middle school education and the CareerStart program, which can be implemented in schools to promote this type of learning. CareerStart is a whole school engagement program that responds to current education reform initiatives and supports more comprehensive efforts to promote school-based professional collaborations that benefit at-risk students.