Although student-centered learning and the components it promotes are increasingly accepted and found extensively nationwide, there still exists minimal academic research that explores the perceptions and lived experiences of educators in transitioning to this educational philosophy. Therefore, the purpose of this study was to explore in specific detail the perceptions and lived experiences of secondary teachers and building principals in transitioning to student-centered learning and thereby assist in filling in the literature gaps surrounding this topic. The participants for this hermeneutical, qualitative phenomenological study consisted of six secondary teachers and four principals and used a constructivist theoretical framework to assist the researcher in identifying and conveying each participant’s deep, rich experience. In-depth interviews were used to gather responses and the data was transcribed and eventually grouped into three major themes, with key words and terms from the participants supporting each theme. The three themes that emerged when identifying and describing the perceptions and lived experiences of the participants in transitioning to student-centered learning were a shift in philosophy of education, changes in methods and pedagogy, and the importance of relationships among teachers, principals, and students. Although teacher and principal participant responses demonstrated some differences in the categories or terms that were identified, each response was still supportive of the same three major themes. Key findings from the study suggest that in order to effectively transition from teacher-centered to student-centered education, cognitive changes in an educator’s philosophy and mindset, along with social adjustments addressing relationships, connections, and experiences, must be recognized and even embraced.