This presentation summarizes how an assessment project designed to understand the transition to college and workload in STEM general education courses also served as a just-in-time intervention strategy to enable first and second year students to discuss what it means to transition to -- and be successful in-- college.  Emphasis will be on the impact on students of falling short—either of their own goals or the goals they perceived others held for them—and to set the stage for appropriate coping mechanisms they could exercise to address the disconnect. The project addresses how undergraduate STEM majors conceive of their college transition, general education courses, and failure but is easily extended to a broader array of disciplines.