Addressing the unequal impact of health disparities on historically marginalized communities is a top public health priority. Diversifying the work force has been lauded as key to addressing this challenge. Contributing to diversity in the workforce is the recruitment and retention of health professionals previously excluded and underrepresented in medicine. A major obstacle to retention, however, is the unequal way in which health professionals experience the learning environment. Through this perspective of 4 generations of physicians and medical students, the authors seek to highlight the similarities that have persisted over 40 years in the experiences of being underrepresented in medicine. Through a series of conversations and reflective writing, the authors reveal themes that spanned generations. Two common themes among the authors are the feeling of not belonging and feeling invisible. This is experienced in various aspects of medical education and academic careers. The lack of representation, unequal expectations, and over taxation contributes to the feeling of not belonging, leading to emotional, physical, and academic fatigue. Feeling invisible, yet paradoxically being hyper-visible, is also common. Despite the challenges, the authors conclude with a sense of hope for the future, if not for them, for the generations to come.