A synopsis of students course taking and the type of diploma chosen by high school students, also known as their Individualized Learning Plans (ILP), provides a holistic view of student's preparation in high school, and serves as a reliable indicator of their college and career readiness. While ILPs are mandated in over 30 states, limited work has been done on measuring their effectiveness in ensuring that students are better prepared for college and career. We thus propose to use propensity score matching to measure the effectiveness of using ILPs by comparing the number of college applications and likelihood of entry into college for students who use ILPs, when compared to students with similar characteristics who do not use this tool. We use data from the High School Longitudinal Study (HSLS) of 2009.