This paper speculates on motivational connections between art making and its reception, the alchemical process, and notions of the spiritual in the art of the outsider. Using Jungian psychology as a theoretical framework, the paper attempts to address the perceived oppositional conditions pertaining to art made from both within and outside the cultural mainstream. Parallels are drawn between the artist and the alchemist as outsiders and how visionary states of mind might be seen as fundamental to aspects of spiritual experience. The paper had evolved out of theoretical issues developed from within my studio and the practice of painting. The idea of the possibility of ‘trans-cultural’ expression emerged from this practice and this was developed theoretically using Jungian and Post Jungian perspectives. In the process, it became apparent that any symbolic meaning appeared to be embedded within aesthetic values and that these ‘values’ as such suggested deep connections to the notion of ‘otherness’ in art and the spiritual. These ideas remain central to my ongoing attempt to invest painting with a level of ‘depth experience’ and to establish the primacy of imagination as the key faculty underscoring perceptual and emotional intelligence