Objectives: To determine the motivation and incentives in education, learning experience and teaching techniques, and expectations about future careers among medical students from a multi-ethnic Asian country. Methods: Pre-validated questionnaire-based survey with stratified random sampling among medical students. The questionnaire combined qualitative responses with semi-quantitative measures of available alternatives. Results: The response rate was 83.1%. The most important factor for pursuing university study was 'prospect of finding an interesting challenging job' (rank 1-75%). Family made a significant contribution in decision making. Given the chance, a majority (67.2%) of respondents would prefer to study overseas. The main deterring factors were cost (67.7%), distance from home (28%), and local opportunity for post-graduation (23.4%). Despite their inclination of study overseas, the majority (73.9%) of the respondents indicated they were either very satisfied or satisfied with their current choice of university study. Only 20% of students were comfortable in asking questions in classroom as asking questions was deemed 'too risky' and 'unnecessary to get better grades'. Students adopted strategies related to assessment and competition to monitor their study. Senior students reported university education as less relevant to their future careers as compared to junior students (p = 0.002). Conclusions: Students' learning behaviour is determined by complex factors such as educational incentives, learning support, assessment and competition. Among several external factors, family, job prospects and expectations about the future play a critical role in education.