This study addressed the problem of identifying challenges and expectations when a school transitions from traditional education to personalized learning. The single case study used semi-structured interviews to discover the experiences and thoughts of ten teachers and staff members from a rural high school that transitioned. The school was in its sixth year of implementation at the time of the study and was functioning as a personalized learning school. The study results showed that this transition required the teachers and staff to be flexible with both an open and growth mindset. Teachers and staff required time to complete the extensive work needed to ensure curriculum, scheduling, relationships, student agency, environment, teaching philosophy, and pedagogy aligned to support student-centered learning. Implications learned in the process of doing the study suggested that school leaders work with teachers, staff members, community members, parents, and students to define personalized learning and its essential elements prior to implementation to create a clear vision and plan for their school. Teachers having an understanding of their standards, student agency, and project-based learning was helpful, along with teachers recognizing that students may have needed to be taught how to use all of those elements. One important element that contributed to a solid understanding of personalized learning was teachers' development of their online, personalized curriculum. Future research could examine the student perspective of transitioning and functioning in a personalized learning school. This study could benefit school leaders and schools planning or considering transitioning from traditional education to personalized learning. [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.]