This study utilizes an autoethnographic qualitative methodological approach in which I explore the ways in which my personal and professional experiences across my lifetime shaped my responses to COVID-19 as a Black principal in an urban school district in southwest Texas, during the 14-month period between March 16, 2020, and May 28, 2021. I focused specifically on my responses to the educational and social-emotional needs of my staff members, teachers, students, and their families during the four distinct transition phases my school district implemented as we educated students during the period of study. I not only described my experiences as a principal during a specific period during the COVID-19 pandemic, but I also analyzed data about myself -- critical events both personally and professionally that influenced my responses as principal during the time of study. Using autoethnography allowed me to be the primary participant of the investigation while a purposeful selection of secondary participants and other data sources enabled me to utilize triangulation to ensure trustworthiness. Bronfenbrenner's Socio-Ecological Systems Theory was useful in analyzing my interaction with various entities within the different systems during the COVID-19 pandemic. However, it was more useful for explaining the context of my study than it is for interpreting the question my study explored - How did my personal and professional experiences influence my responses as principal to the different challenges presented by COVID-19? To effectively explore the question that guided my study, I had to consider myself as the main interpretive tool. I identified the consistent themes across each experience and interpreted how the themes influenced my behaviors as principal during COVID-19.The findings reveal that the personal and professional experiences across my lifetime forced me to live in space that existed at the intersection of courage and fear. My experiences provided the training ground that enabled me to successfully navigate this space throughout my life. The skillset I acquired were the very same ones that allowed me to successfully navigate the challenges presented by the unprecedented COVID-19 pandemic during the period of study. [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.]