In this article, I detail my journey through which I have experienced phenomenology. The article includes theoretical connections, personal aspirations, methodology, data collection, and themes that I have identified as I analyzed the data. I have deep personal connections to the phenomenon in the study, the journey to becoming a school principal, and I explain how those connections influenced the research design for my study. The stories that were shared with me by the participants, school principals from the elementary and secondary level in Massachusetts, are central to my experiences as a researcher in this project. I have included my reactions to stories from participants to develop perspective into my experience that aligns with my personal aspirations of becoming a school principal. The article contains quotes from the participants and takeaways that have emerged through the course of revisiting and analyzing the array of responses provided. As pressures mount and problems become increasingly complex in education, principals shared the responsibility of remaining responsive to these challenges. Though demands of time, energy, politics, and resources have placed complex issues onto school principals, the positive influences that effective principals have on their students, staff, and community cannot be overstated. As one participant recounted, "As a leader, you have the ability to really make a difference in such a profound, broad way." My hope is that their stories can become part of my story and the stories of other future principals.