Training physicians to care for diverse and sometimes marginalized patients requires residency programs to create diverse and inclusive learning environments that address inequity and oppression. Pursuing Diversity, Equity, Inclusion, and Anti-oppression (DEIA) is not about quick fixes but ongoing commitment, humility, and responsiveness to one’s community. In this chapter, we describe one residency program’s imperfect efforts towards DEIA, highlighting key lessons: commitment to DEIA does not prevent mistakes; fostering a culture of loving accountability moves DEIA forward; faculty must embrace feedback and enact change; DEIA work must be integrated into all aspects of the working environment; race-based caucusing is one tool for improving inclusion, equity, and anti-oppression; and an anti-oppressive approach requires creativity and power-sharing with patients, communities, and trainees.