Student engagement is an essential part of the many transitions adolescents must make on their way to self-sufficient adulthood. Motivating students to learn at pivotal points in their school careers, especially as they transition into high school, is sometimes difficult. The Freshman Transition Initiative (FTI) at The George Washington University is doing just that with the blending of a freshman transition course and a 10-year plan with service-learning. The FTI's Course Standards for Freshman Transition Classes are meant to be integrated into all courses, including math, English, and career and technical education. This article discusses how engaging in relevant learning can be a key to successful transitions and highlights the positive outcomes that participants gain from service-learning experience in the areas of personal/social development, academic achievement, citizenship, and career awareness. (Contains 4 online resources.)