The Singapore government has long relied on the inherent public pedagogical qualities of culture in the forms of official cultural and media policies and in the unscripted signifiers of cultural conduct, such as in the public's attitude towards the arts. The prime objective is to instrumentalise citizens on how they should become both economically productive and creative whilst adhering to prescribed sociopolitical norms. The paper begins with a discussion of a 2012 debate surrounding a Singapore street artist, dubbed the "Sticker Lady", who was arrested for vandalising public property with political incorrect stickers and provocative phrases. The saga sparked questions of whether Singapore is ready to embrace the increasingly open, technologically advanced and creativity-led twenty-first century. This paper argues that while the authorities are cognisant of the need to open-up society, it is finding it difficult to cede some aspects of control. Instead of making the case for a fundamental change, it argues that public pedagogical imperatives need to be better applied to realign the direction of cultural policy in Singapore. In essence, the perception of what creativity is and how it might engender sociopolitical openness is needed to "inculate" a culture of creativity in Singapore.