Self-advocacy is the ability to communicate one's needs and wants and to make decisions about the supports needed to achieve them (Stodden, Conway, & Chang, 2003). Research shows self-advocacy skills are related to academic performance and successful adaptation to college (Adams & Proctor, 2010; Getzel & Thoma, 2008; Hadley, 2006; Murray, Lombardi, & Kosty, 2014; Thoma & Wehmeyer, 2005). Yet, few studies have documented how youth learn to self-advocate and even fewer have delved deeply into how or when students use self-advocacy skills in college. Narratives gleaned from eight students with disabilities in a qualitative grounded theory study begin to fill this gap. Participants reported learning self-advocacy skills from family members and educators early in life. Findings from this study also demonstrate that college students utilized self-advocacy skills in three different ways: proactively, reactively, and retrospectively. Recommendations to enhance the self-advocacy skills of students with disabilities are provided for family members, K-12 personnel, and postsecondary educators.