This study aimed to investigate the difficulties and coping strategies of youths with learning disability from school to workplace. To do the in-depth, phenomenologically-based interviewing, this study invited five participants who were qualified with learning disability during their time of schooling. These five participants who have been employed and maintained the state of working stably were interviewed to share their life stories about learning disability. The result of this study presented different manifestations from which each participant displayed, including the progresses of learning and working, strategies to cope with difficulties at each environment, and how they regard their learning disability. The study also analyzed factors that improving youths with learning disability to accommodate the environment. Based on the result, the study proposed some suggestions for further researchers, educators, associations of learning disability, individuals with learning disability, and works in vocational rehabilitation.