Medical students, residents, physicians, and caregivers have struggled during the pandemic. The times in which we live will transform medicine. These essays, drawn from the Kern Institute's Transformational Times newsletter, offer glimpses into what we have experienced and what might yet come. In these pages, readers engage with unsettling realities unmasked by COVID-19, including workplace biases, inattention to wellness, residency-related stress, the loneliness of military responsibility, the inequity of the world around us, reproductive healthcare uncertainty, new educational realities, and the imperative for flourishing and practical wisdom in physicians. Each essay reveals remarkable insights and reflects the interplay of the world we inhabit with the present and future of medicine and healthcare.