This qualitative study examines the transition to life after high school of three young men with learning disabilities (LD). The research focuses on their individual journeys from the end of grade 12 in June until to the end of May the following year and provides overarching themes as to their lived experiences during this year of transition. Using a longitudinal multiple instrumental case design, a series of four in-depth interviews were conducted with each of the three participants. The findings showed that although the students had unique experiences over the year, there were several commonalities in their stories including readiness, emotions, the importance of social connections, coping skills, changes over time, accessing supports, and learning online. We discuss the stories of the participants based on these overarching themes. Although the study only examined the experiences of three men with LD from one high school, their stories provide valuable information and highlight several recommendations for supports and services, such as types of support offered to students and the timing of these supports. Moreover, their stories highlight the need to develop a positive sense of self during the high school years, and social integration once on postsecondary campuses.