This qualitative study examined the role and determinants of motivational beliefs and self-perceptions among six academically successful undergraduates with learning disabilities at private 4-year colleges who serve as mentors for middle-school students with similar learning challenges. Drawing on the expectancy-value theory of achievement-related decisions as a framework for understanding academic trajectories, themes focus on a) participants' social and cultural milieus, b) socializers' beliefs and behaviors, c) disability-related experiences, and d) individual goals and self-schemata. Findings countered expectations that sociocultural influences would hinder students' expectations for success and the importance they place on college education. Instead, protective factors including participation in rigorous high school coursework, high parental expectations, and membership in a learning disability community supported the decision to pursue and persist in post-secondary education.