Existing anthropological accounts have tended to portray the normative ideal of the modern subject as predicated on the demand that the materiality of semiotic forms such as the body and words be subordinate to the subject's interiority as a condition of possibility for his or her freedom and moral autonomy. In this article, I seek to contribute to the ongoing and fruitful conversation in anthropology over the idea of the modern subject by highlighting the distinguishing features of a specifically modern normative ideal of creative agency in which the materiality of semiotic forms is fully incorporated into the architecture of the self and is seen as a condition of possibility for its articulation. This norm is epitomized in the notion of self-expression that has emerged from Sentimentalism and Romanticism. In doing so, I draw on fieldwork I conducted in creative writing workshops in Israel and U.S. postsecondary jazz education, as well as on U.S. self-help literature. I argue that this normative ideal of modern creative agency qualifies the assumption that modernity has been predicated mostly on the desire to keep nature and culture ontologically distinct. I conclude the article by exploring this normative ideal as it resurfaces in the present historical moment in modern subjects’ attempts to orient themselves under conditions of neoliberal uncertainty, open-endedness, and potential creativity.