This paper analyses reflections upon the nature of recent educational policymaking in Singapore. Drawing upon the authors' individual and collective autoethnographic analyses of a series of reflective notes jotted down after discussions with educators from private and public schools in Singapore, the Academy of Singapore Teachers, and FutureSkills Singapore, we argue that what we learned from this Singaporean experience is considerably different from how the 'success' of the Singapore model is construed in much national and international policy about educational reform. While the research confirms various key paradoxes [after Ng, Pak Tee. 2017. "Learning from Singapore: The Power of Paradoxes." New York: Routledge] that exist in relation to how schooling is construed within the Singapore context, there is also evidence of a form of pragmatism existing alongside a yearning/striving for perfection that is perhaps reflective of more active and directive practices and processes. Through identifying what we describe as 'pragmatic perfectionism' in the Singaporean context, we not only substantiate but also seek to extend existing understandings of educational policy learning/borrowing in comparative education literature, identifying the intensity of such processes as one of the 'real' lessons that national and international policymakers and researchers should and can learn from the Singaporean case.