In March 2020, schools along with businesses across the United States began to shut down as a result of COVID-19. In addition, the slayings of George Floyd and Breonna Taylor would spark civil unrest during the polarizing election year with President Donald Trump and former Vice President Joe Biden on a crash course to be elected as the commander in chief of a divided nation. The following memoir centers my experience as a Black man in my first official year as a vice principal during this arduous period. In addition, I connect my time as a teacher-leader in 2016, highlighting the overall difficulty of leading while navigating individual and collective trauma as a member of a larger Black community.