Student engagement in education is key to ensuring successful learning. Engagement becomes crucial as students progress through high school and transition into young adulthood; however, engaging them in high school can be an arduous task. A career/education plan can help students make strong connections between their work in high school and their later lives. Through two-level propensity score matching analyses using data from the High School Longitudinal Study of 2009, this study explores the direct relationship of completing such a plan and student engagement late in high school. I found that completion of a plan had a positive significant relationship with student engagement. These results held true for the entire sample and for the public school sample. This information adds to the growing research on career and college readiness and to more limited literature on the role of education planning in high schools.