Students who do not graduate from high school in four years can choose to attend alternative high school programs. Students attending alternative schools have risk factors preventing them from being successful in traditional schools. Examples of risk factors include being over-age under-credit, parenting as teens, living in poverty, and managing emotional concerns. The problem addressed by this study was that 50% of the students attending alternative high schools fail to graduate, and at times, this failure was attributed to self-sabotaging behaviors. The purpose was to examine experiences of alternative high school students aged 18-25 relating to self-identified self-sabotaging behaviors. The conceptual framework was Schlossberg's theory of transition, a process, and model designed to understand the feelings surrounding transitions to positively navigate normal life transitions, of which graduation is one. The participants were 14 individuals, who dropped out of high school, graduated, or earned a high school equivalency from an alternative high school program within 2016-2019. The research questions were designed to understand the participants' experiences and identify strategies to help eliminate self-sabotage. The findings suggested a successful transition to graduation relied on understanding feelings associated with changes relating to the transition. Anxiety surrounding the transition of graduation can create a sense of lost control or judgment of self-worth, which can lead to self-sabotaging behaviors. Recommendations for practice included focusing on the climate and culture of a school while providing meaningful feedback, creating an atmosphere for successful transitions. Recommendations for future research included expanding the current sample population to comprise students with risk factors attending traditional schools. Additionally, collecting quantitative data to isolate variables could offer insight for a deeper understanding of students' motivations who display self-sabotaging behaviors. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]