Singapore’s education system has remained consistently near the top of most education ranking systems over the past decade. OECD (2010) attributes the success to a systemic focus on curriculum innovation by Singapore schools. However, the challenges that emerge from the various initiatives are complex and multifaceted. Using the lens of Schwab’s (1973) four commonplaces- milieu, learner, subject matter and teacher, the experienced curriculum is unpacked to reveal the discourse of the challenges of curriculum translation. While I examine the similarities and differences in curriculum translation under two different educational philosophies- curriculum vs didatik, I attend to the educational outcomes of teaching practices using the Appreciative Inquiry approach. The challenges than unmask the inherent tensions between socio-economical ideologies with the curriculum implementation at the programmatic and institutional level. Exploring from Engestrom's Activity Theory, I will examine the issues of ideology and control surrounding what gets eventually translated in the classroom curriculum.