In this report, the Rennie Center for Education Policy & Research focuses on Individualized Learning Plans (ILPs) as a key tool that districts and schools can use to prepare students for college and career success, as well as the costs districts incur to implement ILPs. In Massachusetts some public school districts have utilized ILPs to pursue a holistic approach to college- and career-readiness that aligns with students' academic, career-based, and personal and social growth. Based on a scan of recent literature, the Rennie Center identifies effective practices in developing ILPs to support college- and career-readiness. Then, the team highlights districts and schools that have been using differentiated approaches and strategies to implement ILPs and are at varied stages of implementation. Finally, the research team compiled cost estimates for replicating ILP strategies across Massachusetts public school districts. The research team selected districts for participation in the study to reflect different stages of ILP implementation, focusing on: planning and piloting, the first year of roll-out, and sustaining progress and scaling. By documenting ILP practices in various stages of implementation, the Rennie Center team hopes to highlight the use of an innovative college- and career-readiness strategy that can instill in students a critical set of 21st century skills that support long-term life success. Included in this research study are programmatic profiles of: (1) Monson High School; (2) Minnechaug Regional High School; (3) Leominster Center for Excellence; and (4) New Bedford High School. [This report was co-produced by the Massachusetts Budget and Policy Center.]