<p>According to virtue jurisprudence, good laws can be conducive to virtuous living; poor laws can contribute to character vices and entrench prejudices. This article focuses on what lies beyond the strict categorization of virtue and vice simpliciter—the ethos and mindset of a people. Using a case study of Singapore, this article examines how law, conceived of in the broadest sense as including policies chosen in a legal regime that leaves the concretization of policies to government bodies, can diminish the capacity and desire of individuals to live examined lives in pursuit of <i>eudaimonia</i> or flourishing. Insofar as living examined lives in pursuit of flourishing is good according to virtue jurisprudence, such laws deteriorate the ethos of a society and, by and by, the character of individuals. Living unthinkingly in pursuit of a narrow conception of success because others do so is the counterfeit of living an examined and flourishing life. I examine how the ethos of pursuing the narrow conception of success emerged in Singapore’s phase of rapid nation-building. I consider how the government of the developed nation now regards such ethos as lacking and suggest how the nation can be purposefully redirected towards flourishing.</p>