Experiences in medical education have changed significantly in the last two decades. This evolution is apparent in the teaching/ learning environment, types of education resources and learners. In this article two students provide a reflective account of their individual journeys in medical education spanning across 20 years. While some things remain unchanged, significant differences emerge that stress upon the educators and institutions to stay mindful of these transitions in order to develop learning environments that nurture the growth of future physicians.Experiences in medical education have changed significantly in the last two decades. This evolution is apparent in the teaching/ learning environment, types of education resources and learners. In this article two students provide a reflective account of their individual journeys in medical education spanning across 20 years. While some things remain unchanged, significant differences emerge that stress upon the educators and institutions to stay mindful of these transitions in order to develop learning environments that nurture the growth of future physicians