The completion of high school is often seen as an exciting time for young adults. For students with disabilities, however, this can be a difficult time filled with uncertainty if they have not had sufficient planning and preparation for adult life. Transition refers to the process of preparing individuals for changes as they move from one stage of life to another, such as the shift from school to adulthood. However, this process often presents new challenges and responsibilities for youth and young adults with disabilities and their families. This study employed a qualitative approach using semi-structured interviews to gain insights from adults with severe disabilities regarding their experiences in pursuing independence, including the challenges they encountered and the strategies they used to navigate life after leaving school. Ten participants from Taiwan, all with severe to profound disabilities, were interviewed. The findings revealed various strategies that supported their pursuit of independence, such as family support, self-advocacy, and the use of societal or public long-term care services. Participants also identified barriers and challenges, including a shortage of caregivers and limited access to services. Furthermore, the findings highlighted how policies, societal values, and attitudes in Taiwan influence their journey toward independence. By exploring the experiences of older individuals with severe disabilities, this study underscores equity issues and individual-centered perspectives, offering implications for youth and young adults with disabilities and their families as they navigate the transition to adulthood.