Anzaldúa’s liberatory social theorizing and praxis are centrally inspired by the notion of the simultaneity of self and global transformations. In this article, I explore how Anzaldúa develops and applies her approach through the writing of Borderlands/La Frontera: The New Mestiza (1987). I will begin by noting that for Anzaldúa, the transformation of self/world essentially involves the task of healing/transcending/bridging a vast array of habituated dualisms deeply ingrained in our personal and global landscapes. I will use C. Wright Mills’s notion of the sociological imagination, and Gurdjieff’s view of the human “individual” as a “three-brained being” and site of multiple selves, to frame and provide a preliminary answer to this question of what is so transformative and energizing in Anzaldúa’s work. I will close with the relevance of the foregoing to the new agenda advanced in my work in the frameworks of human architecture, sociology of self-knowledge, and utopystics, as methodological, theoretical, and historical-practical exercises in imaginative applied sociology-one that dialectically engages both micro and macro, quantal and Newtonian, sociological imaginations in favor of simultaneous self and global transformations. The creative/poetic exercise of self-knowledge and transformation in an increasingly global and world-historical context is a human right, and awareness of and training in it must be a fundamental “Gen Ed” requirement comprising any serious liberal arts education in our colleges and universities.