The disengagement that leads to school dropout may start as early as middle school, but may be interrupted by motivational interventions. One approach is to promote the relevance of content through explanations and demonstrations of the value of this content to students' futures. CareerStart is an intervention that provides teachers prepackaged lessons for middle school math, English language arts, science, and social studies, which connects content in these courses to jobs and careers. In this study, we use data from a randomized control trial to report on the impact of CareerStart and career relevant lessons on preventing later drop-out. Event history analysis shows that CareerStart reduced the hazard of drop-out by 23%, and that at the school level, 10 CareerStart lessons was associated with a reduction of 1%. Students who did not change schools experienced the greatest benefit. We discuss implications for practice and research and suggest next steps.