As a medical student finishing my preclinical education in April 2020, the medical community’s response to the COVID-19 broadened my understanding of the skills required to be a physician. The pandemic forced me to confront my discomfort with unpredictable circumstances, including those surrounding USMLE Step 1. Reflecting on my discomfort and the role uncertainty plays in the lives of those in the medical community, however, inspired me to develop the skills I need to better face uncertainty in my career. I found that personal engagement with concepts introduced during my psychiatry curriculum promoted resilience. In particular, I relied on selflessness and trust to connect with the medical community. Selflessness and trust are direct products of the mature defensive mechanisms of altruism and suppression, which I studied extensively but never engaged with on a personal level. I now believe that teaching psychiatric topics through self-reflection can help medical students identify ways to manage their own discomfort and cultivate resilience and personal growth. In this paper, I discuss how my preclinical education both encouraged and complicated my own development of trust and selflessness, how witnessing examples of trust and selflessness reconnected me with the medical community, and how personal engagement with the study of mature defense mechanisms promoted comfort with uncertainty.