Podcast host, Ann Hui, is the first NUS Medicine student to have taken a gap year with the Yale-Visiting International Students Program before returning for her clinical years. Two juniors, Caitlin and Ying Ying embark on the same journey a year later. Amongst the three of them, they took a diverse set of classes which include medical anthropology, documentary film-making, engineering, and architecture. Now that they are back in Singapore, they share about their lessons at Yale and how they are applying or adapting what they have learned to Singapore’s context to be better informed medical students and future doctors. They also reflect on their initial motivations for taking a year off medical school and offer some advice to fellow students who aspire to go beyond their calling in medicine.