In this autoethnography, I examine the challenges I faced as a private-to-public-sector novice CFO entering a resource-constrained 41-thousand-student K-12 urban school district in Colorado. This study chronicles how I deliberately slowed down my interactions within a complex adaptive system (CAS) through ethnographic interviewing to identify the relationships, processes, and tools; and create the conditions necessary to align and optimize resources at the district level to improve student outcomes. There is scant research on how a new K-12 education CFO transitions from a traditional budget-manager approach toward one that promotes inquiry and cost-effectiveness. Unlike CFOs in the private sector, oftentimes I was estranged from strategic and capital-allocation decisions, particularly around instruction. I lacked the time, skilled staff, and resources to perform fundamental cost-benefit analyses. I had come to work in a school system after obtaining an MBA from the Stanford Graduate School of Business and working in Wall Street for 20 years. Having no experience working in the public sector more generally or education more specifically, I came with a particular mindset and approach not altogether suited for this environment. Consequently, my transition to this new milieu was quite chaotic. I intentionally embraced entry planning as a way to make sense of a CAS that oftentimes defied comprehensive analysis. I learned, slowly, that successful entry required intellectual rigor and emotional sensitivity. I repeatedly found that interventions based on adaptive change that fundamentally shifts how works gets done increased employees' anxiety. I assumed the roles of researcher, learner, and knower in evolving an induction approach that recognized entry never stopped because the CAS never rested. I explore entry through three case studies. The first of these pertains to my participation in Teachers' Master Agreement Negotiations; the second centers on my engagement with Nutrition Services, a low-status but high-value allocator of resources; and the third analyzes how I merged the roles of CFO and educator to increase my district's understanding of municipal-bond finance in preparation for a general-obligation bond offering. [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/en-US/products/dissertations/individuals.shtml.]