This study explored the motivation of underperforming students at three points of time: applying the programme, studying in Year 1 and during their repeating year due to academic failure. Six underperforming Year 1 students were interviewed on their initial motivations for choosing the medical programme. Triangulation of analysts was applied in the narrative analysis. Later, these students completed the Academic Motivation Scale (AMS) questionnaire twice to reflect on their learning experience in Year 1 and their repeating year. Results showed that these students initially had a mix of amotivation, intrinsic motivation and extrinsic motivation upon applying the medical programme where the worst case scenario was that students genuinely “did not know why”. It was further shown that their motivation for studying medicine was unchanged, increased or decreased over a period of time. Although this study fails to support the notion that initial motivation matters in influencing academic success, the AMS results proved that student motivation could also change over time. Hence, more effort is needed to nurture intrinsic motivation after enrolling into medical schools.