Purpose: Singapore's education system is known for its robust curriculum and excellent results. It is also a system of keen competitiveness and high pressure. This article addresses how such an education system responds to the issue of student well-being. Design/Approach/Methods: This article analyses the recent initiatives and shift in education philosophy in Singapore's education system, which have a bearing on the issue of student well-being. Findings: This article argues that while there are direct efforts to address student well-being, the direction Singapore is taking is to pursue a holistic education paradigm, in which education is engaging, joyful, meaningful, and values-based. This article also argues that such a paradigm goes beyond the current well-being agenda and is aligned with a view that education should be about wholeness and purpose. While there are challenges associated with these changes, the Singapore experience suggests that the more we focus on holistic education, rather than interpret student well-being narrowly, the more wellness the students may actually and eventually experience. Originality/Value: This article brings to readers learning points from Singapore regarding student well-being, as the country grapples with change to develop a generation of young people, whose "beings" are and will continue to be "well."