Students have dreams and goals outside of school. School psychologists can play a vital role in helping students with disabilities reach their dreams, particularly when the dreams ask the question “What do I want to do after high school?” Often, the answer lies in postsecondary goals, which require transition planning while the student is still in school. This paper explores how families, teachers, and school psychologists can all play supportive and distinct roles in helping a student with disabilities reach their postsecondary goals. There have been several transition models proposed to help students with disabilities shift from PK-12 to postsecondary settings; however, there are gaps in application for the most important team members: student, family, teacher, and school psychologist. Lastly, this paper proposes a new transition framework, Creating a Roadmap: Providing Opportunities for Optimal Living (CAR:POOL), that focuses specifically on the concrete steps a transition team needs to complete postsecondary goals.