As instructional coach at Spring Grove Area High School in Pennsylvania, the author realized that too many of the school's freshmen were becoming what one might call lost in transition; they never made it to their sophomore year. He joined with concerned teachers and counselors from the school and its feeder middle schools to create a freshman advocacy group and eventually a successful peer mentoring program. The program trains upperclassmen to serve as one-on-one mentors to freshmen identified as at risk for academic failure. Mentors also raise money to buy school supplies for all their at-risk peers, and mentors and mentees have come together to raise money for groups like Habitat for Humanity. After several false starts, the program is helping a majority of students it serves succeed in classes and transition successfully to their sophomore year.