The goal of this research is to examine how implementing a new pedagogical structure, Academic Choice, informs my understanding of my students as learners and individuals. Using a self-study methodology over the course of eight working sessions in my Kindergarten classroom, I collected multiple forms of qualitative data, including student work samples, focal student observations, structured interviews, and research journal entries containing my own reflections as well as notes on consultations with critical friends. These data were analyzed inductively by connecting observations and patterns from across these sources. Findings indicated that providing a choice in content allowed struggling students to self-differentiate, that one-on-one interactions were essential to understanding a student's choice and work process, and that advanced students needed support to challenge themselves. Furthermore, I found that developmental stage, time allotted for working, and social construction of knowledge were important factors to consider in structuring these working sessions.