This paper describes the findings of an exploratory study for a pilot program in teacher education that employs contemporary Indigenous art as a forum for increasing and enriching teacher confidence and agency in the meaningful inclusion of Indigenous content across K-12 curriculum. Building on a model of transformative education through dialogue, the phenomenological process for engaging with art presented in the pilot workshop asked participants to question not only their own assumptions about Indigenous art and artists, but also to examine assumptions about themselves within education. As such, the phenomenological depth of art explorations provides a mechanism for developing decolonial literacy, a pedagogy for antiracist and transformative education (Bacon, 2015; Curry-Stevens, 2007), and a means of creating ethical space (Ermine, 2007). Our question as researchers explores how the approach of looking at contemporary identity-based Indigenous art in the context of a larger dialogue around the colonial construction of Indigenous identity supports and encourages the sensitive inclusion of Indigenous content in school curricula. Our findings suggest that looking at the self-representations of contemporary Indigenous people can open up a dialogic space between settlers and Indigenous people in ways that encourage student teachers to think more deeply about their relationship with Indigenous peoples and how they might engage in a more inclusive curriculum with their own students.