Research with middle school students has indicated that they are ready to talk about college and careers. However, these students need and desire direct instruction to understand how to prepare for these goals. Future Quest Island (FQI), an online accessible tool and curriculum, was designed to jump-start middle school students’ thinking about college and careers and facilitate teacher engagement in college and career conversations for students in grades 6–8. In the final year of the five-year project, 15 schools participated; findings from a research study that focused on the 6 classrooms with the strongest fidelity are discussed in this publication.