In 2020, the COVID-19 pandemic, the murder of George Floyd as well as other Black Americans, waves of violence against Asian American communities, and the 2020 presidential election created a national climate in the United States that almost defies description with regard to historical significance, collective emotional pain, and the urgency of the resulting calls for justice-focused action. This article explores the experience of three White psychologists/psychologists-in-training within this national context, and specifically, the impact on psychology training and supervision in the wake of the Executive Order on Combatting Race and Sex Stereotyping released in September 2020. Consistent with the extant literature in our field, we understand supervision to be an essential space for in-depth attention to trainee development around cultural humility and critical consciousness wherein we as supervisors also grow and deepen our own practice (Falender et al., 2013; Hook et al., 2016). As we navigated 2020, we found several key supervision processes particularly salient, including antiracism in supervision as mindful practice, facilitating learning while doing our own learning, supervisor consultation, and recognizing the impact of privilege on these processes. (PsycInfo Database Record (c) 2023 APA, all rights reserved).