Phenomenon: Trainees from racial/ethnic backgrounds underrepresented in medicine (RE URiM) in the United States face challenges of racism and micro- and macro-aggressions during residency. Many have learned to navigate these challenges through successes and failures, but there is insufficient literature providing these lessons to graduating URiM medical students. Our study among medical school alumni explores strategies to help graduating URiM students prepare for success in residency. Approach: We conducted an online cross-sectional survey (Qualtrics) from February to March 2022. Graduates from a Northeast U.S. medical school identifying as URiM were invited to participate. With emphasis on “thriving” in residency training, we solicited rating-scale responses on preparedness for residency and open-text responses on strategies for success. Standard statistical and text content analysis were used to determine findings and themes. We used Word Cloud technology to further explore word frequency and patterns. Findings: Of the 43 alumni contacted, 23 (53%) completed the survey. Participants were trained in various specialties. We identified three themes with regard to strategies for thriving in residency: (1) importance of identifying and seeking early mentorship; (2) importance of identifying and having diverse forms of support; and (3) need for more education on navigating macro/microaggressions. Insight: While advocating for systems-level interventions to create inclusive learning environments, we highlight the gap in trainee awareness of the importance of seeking early mentorship. Our study provides strategies for graduating URiM medical students to succeed in residency based on respondent experiences. These recommendations should inform medical school curricula.