The Self-Directed IEP has been found effective in increasing student participation in the first Individualized Education Plan (IEP) meeting following Self-Directed IEP instruction. To date, no published reports have examined the extent students are involved during their second IEP meeting following Self-Directed IEP instruction. This study presents an exploratory mixed method case study analysis of a student with a learning disability in sophomore and junior year IEP meetings to illustrate the difference a year can make in IEP meeting participation, the development of postschool goals, confidence, maturity, and self-advocacy. Results indicate a marked increase from year one to year two in the student’s word count and speaking rate, a more focused postschool employment vision, and an increase in meeting leadership. Discussion of these results and suggestions for additional research are offered.