This session engages Program Directors on topics submitted by attendees with what they struggle with. This year's selected topics are (1) How best to support underrepresented in medicine (URM) fellows, (2) Improving trainee morale and promoting wellness/resilience, and (3) Advancing on a clinician educator track in academia. Moderated by Retreat Chair Nishin Bhadkamkar, MD, Immediate Past Chair of ASCO's Oncology Training Programs (OTP) Committee and Program Director at The University of Texas MD Anderson Cancer Center, and Retreat Co-chair Annie Im, MD, Chair of ASCO's Oncology Training Programs (OTP) Committee and Program Director at University of Pittsburgh.