This paper attempts to discuss how the Singapore Education System is shifting towards student-centred designs and pedagogies, yet retaining a unique Singaporean orientation. It complements the McKinsey report by analysing directives and efforts to understand trade-offs, consequences, and insights for moving forward. The paper uses an ecological view to acknowledge that education systems are complex--historical, contextual, and cultural dimensions shape Singapore's trajectory. Building on understandings of high-performing systems, Singapore's trajectory, and informed by education research, the paper distils three shifts (from a systems level of analyses) which are currently on course: (1) hybridising pedagogies; (2) levelling up the base of lower achieving students; and (3) recognising diverse talents. The paper postulates a gradual, evolutionary stance and for continuing dialogue and alignments in the change process. The paper draws implications by proposing mitigating approaches in Singapore's continuing journey of balancing high academic achievements and twenty first century, inquiry-oriented learning.