Youth with disabilities, compared with their typical peers, have a higher likelihood of dropping out of school and experience poorer transition outcomes. Evidence supports programs and interventions focusing on inclusive education and leadership skills results in successful transition to college and career. This article describes the experiences of six youth with and without disabilities as they participate in the Youth Empowerment Series, a project helping students navigate the path to postsecondary education and/or employment. A phenomenological approach and photoelicitation was used to gather information about participant’s transition experiences. Findings suggest participants valued forming personal connections and friendships as they entered adulthood. Themes included acceptance, leadership, self-advocacy, inclusion, and planning for future goals. Participants were aware of transition needs and goals and had an understanding of the support systems needed to reach their goals. Future research on the role of friendship networks in transition planning as a natural support is warranted.