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Singapore’s education system achieves exceptional international assessment results but operates on consequentialist pragmatism that values outcomes over intrinsic goods. Using Finnis’s Natural Law Theory, this paper examines how the system instrumentalizes knowledge, marginalizes aesthetic experience, and devalues play—three basic human goods essential for eudaemonia. Despite recent reforms, high-stakes examinations and shadow curriculum practices perpetuate strategic learning behaviors that undermine genuine human flourishing. The analysis reveals how even “successful” students and schools may lose in terms of authentic development. The paper proposes specific reforms to promote knowledge as intrinsic good, enhance aesthetic education, and revalue play, creating a more ethical education system that fosters holistic human development beyond mere examination excellence.