Critical reflection and transformative action in a cyclical rhythm are the fundamental features of the process of praxis (Freire, P. [1970]. Pedagogy of the oppressed. Continuum). A self-study methodology was used to explore the lead researcher's pedagogical experiences teaching at a youth development center (YDC) while utilizing praxis as critical reflection. Those pedagogical experiences included both teaching physical education to the students at the center, and instructing a cohort of Physical Education Teacher Education (PETE) students as they participated in a field experience there. The research question that guided this study was: how have the lead researcher's pedagogical experiences at a YDC prompted praxis? Data were expanded upon in recorded interviews with an experienced colleague who probed and interviewed the lead researcher. Interview data were interpreted using qualitative methods. The findings of this study are derived from the lead researcher's critical reflections and are organized into two major themes: (a) unexpected success prompting praxis: a vignette … and (b) praxis prompting pedagogy as an early teacher educator. The first theme describes the lead researcher's initial experiences while teaching physical education at the YDC. The second theme outlines the lead researcher's critical reflection and pedagogical experiences while teaching preservice teachers using the YDC as a context for a field experience. Lastly, the implications of his pedagogical experiences at the YDC are discussed.