Most of us know that, despite the counsel of the current Supreme Court, colorblindness does not comport with our cognitive experience of the real world. Thus legal scholars, backed by cognitive scientists, have called for a move from colorblindness to color insight -- defined as an understanding of race and its pervasive operation in our lives and in the law. This Article is the first to explore the role of research-grounded mindfulness-based contemplative practices in enhancing what may be called Colorinsight, and to suggest specific practices that assist in its development not only of personal capacity to deal more effectively with race, but, more importantly, of the tools necessary for effective collaborative social change in the 21st century. The Article breaks new ground in at least three important ways: (1) it furthers efforts to push beyond the important but limited cognitive turn in understanding racism and discrimination and deepens understanding not only their emotional but relational and systemic aspects; (2) it mines a rich body of research on mindfulness as a means of supporting cross-racial interactions and systemic change that has gone unnoticed in the legal domain, and uncovers the ways that the law school classrooms and other organized spaces currently tend to keep emotional-awareness and interactional-awareness out of legal education practice and discourse, and fail to create space for developing positive racial interactions and skill-building in the classroom; and (3) it offers more than two dozen specific, original or adapted practices for individual, interpersonal and systemic support in opening up space for conversation, learning, and development of positive interactions across race-based and other identity differences.