This bricolage of critical personal history self-study considers how one school administrator has come to understand his roles, responsibilities, and the formation of identity within the context of a school system while envisioning the divergent possibilities of a yet-to-be-known future through the lens of love. During the self-study process, affective experiences were reflexively interrogated to draw out and unpack themes regarding one lived teaching life. Personal positionings, over time, have emerged as a crucial part of the self-study process of studying “one’s self, one’s actions, one’s ideas, as well as the ‘not self’” (Hamilton & Pinnegar, 1998, p. 238) as a means to address and explicate previously misunderstood privileges. The criticality of the study can be found in the ways in which the relationships between power, authority, knowledge production, and contextual social relations, are illuminated and mediated. School as place situates many considerations of the study, whereby Alcoff (1991) suggests, place may be a “social location, or a social identity” (p. 7)—the place of unfolding and enfolding of memories, encounters, and history within the confluence of past, present, and a possible future. The primary research question that has been considered throughout this study is, “How can I use self-study to better understand Albertan education in this current moment, and how and in what ways can my current pedagogical understandings allow for divergent future educational possibilities?” Throughout the process of the study, evidence in the form of non-linear (re)collections of stories bring to light the evolution of metaphorical understandings of past experiences of schools and schooling, and teachers and teaching. Considering these moments reflexively through personal history self-study has allowed for the critical illumination of some ways in which the current iteration of Albertan, positivist, assurance-focused education could afford for future iterative possibilities. The shifts in leadership responsibilities as outlined by Bedard and Mombourquette (2015) have served as implicit groundings of the current context of education in Alberta. Through the consideration of pedagogical metaphors (Gereluk et al., 2016) and associated entailments (Davis & Renert, 2013a, 2013b) within the evidence of the self-study, schema and paradigms, and the affordances allowed were considered. Ultimately, my self-study has emerged as a story of impact and possibility—perceptions of the subtle perturbative impacts on primary and secondary teaching practices, pedagogies, and paradigms, and the possibilities for the evolution of teaching pedagogies from reductionist and positivist towards enmeshed, relational, ecological-sensibilities and pedagogical possibilities of love.