This dissertation research chronicles my experiences with emotions and learning as a student conduct administrator throughout the arduous process of investigating, becoming, and transforming by engaging sociocultural theory. Grounded in Authentic Inquiry (Tobin, 2006), this research centers my lived-experience and nuances the role of emotions in student affairs and especially student conduct practices. Throughout this dissertation I address themes surrounding reflexivity (Bourdieu, 1992), emotions (Turner, 2002) (Collins, 2004), and self-care. Each chapter is interpretive and impressionistic and represents my thinking as a researcher and conduct administrator. Throughout the chapters I narrate salient events and experiences in my student conduct practice as I interpret what is happening and why it is happening. This is a manuscript-style dissertation with four distinct chapters that can be read alone or in conjunction with each other. Two bookend chapters, chapters one and six, summarize where I have been as a researcher and scholar and where I am going in in regard to future research respectively. The final chapter, chapter seven, I wrote as a postscript after my oral defense. Chapter two was previously published in "The Business of Education." It establishes the foundation of student financial aid and the macro-level structures in place the prohibit students from accessing higher education equitably. The work in this section represents the beginning of my trajectory where I focused on examining macro-level educational structures. It also signifies my departure from traditional research that aligns with post-positivism and frames my thinking after a tumultuous first-year experience in the doctoral program. Chapter three explores the use of heuristics as shapeshifting tools for building awareness and ameliorating emotions in student conduct work and is a forthcoming section in "Transforming Learning and Teaching: Heuristics for Educative and Responsible Practices." Chapter four is an impressionistic tale that explores issues of trauma, emotions and boundary-setting through event-oriented inquiry to explore a "spike" in the curve during a student conduct interaction. Chapter five delves deeper into ameliorating emotions and wellness challenges that I experienced during the COVID19 pandemic. Also, in chapter five, I explore the impacts of self-care and wellness regarding food as a coping mechanism. In chapter six, I close the dissertation with a review of changes in practice I am making going forward and insight into the systems of support that made this research possible. In the final section, chapter seven, I respond to feedback I received during my oral defense that clarifies my stance on teaching and learning. [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.]