This paper outlines an ongoing qualitative review of themes that have emerged across the various session of the "Paint Your Life" program which was developed over the last 15 years. The author discusses the potential for "Paint Your Life" to disrupt hegemonic discourse about art, artists, and community development. Based on the qualitative collected from across different international sessions the author suggests that "Paint Your Life" offers a radical means for re-imagining international education policies and art discourse, including the ways in which the arts, in the hands of various community groups can create "border crossing" between artists and non-artists, between school and community, between cultural distances, and between self and "Other." The early research into this program anticipates how "Paint Your Life" might contribute to anti-oppressive aesthetic community projects.