In philosophical discourse, vagueness is commonly regarded as an undesirable and problematic aspect of human experience. Such standpoints are not unfounded. However, in this article, I argue that vagueness may in certain instances also possess an instrumental role that supports specific modes of human aspiration, including the artistic and the mathematical. In particular, I investigate the ways in which vagueness not only hinders but also fosters the emergence of an aesthetic quality of experience during the imaginative endeavours of fine art (...) and mathematics. The manner in which the benefit from felt vagueness ties into the formation of artistic and mathematical scenarios helps to illuminate deep and often unnoticed relations between these two domains of human ingenuity. In this article, the overall concept of experience and the particular features of human experience, such as the aesthetic and the vague, are examined in the context of John Dewey’s philosophical pragmatism. In Dewey’s philosophical framework, the human mind and culture are understood as natural phenomena. As such, the Deweyan approach fits the paradigm of a twenty-first century scientific understanding of the inherent ontological unity of all modes of human existence and activity. (shrink)