As the world contends with a global pandemic, climate catastrophes, white supremacy, coloniality, and concurrent genocides my attention splinters. In an act of futurity, or future making, I ask myself: "What is needed to move from this place toward softer, more liberatory futures?" This body of work finds its answer in exploring two interrelated concepts: "Decentering Whiteness" and "Holding Complexity. Decentering Whiteness" is the process of working toward a future where all the personal, spiritual, educational, epistemological, social, structural, psychological, financial, and systemic ties to white supremacy are unraveled. "Holding Complexity" weaves together knowledges of care, accountability, intersectionality, and assemblage. It illuminates a potential path toward that imagined future of "Decentering Whiteness." It is defined here as the practice of continuously working to challenge and expand one's knowledge, language, and lifestyle for the purposes of more deeply understanding and caring for those we engage with. Weaving together Critical Social Theory, Black Feminisms, Decolonial Theory, and art this dissertation highlights three projects that reflect on the concepts of "Decentering Whiteness" and "Holding Complexity" from different vantage points in differing contexts. The first project is a critical thematic analysis exploring how white LGBTQ+ youth engage with whiteness and white privilege. The second project is a comparative case study that examines the similarities and differences between two cohorts of the Decentering Whiteness Workshop series. The third is an autoethnography that explores the complexities of incorporating these concepts into pedagogical frameworks and teaching. The three projects highlight uses of these two concepts, the importance of context, as well as the necessity for change in how we create educational spaces here in the United States. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]