Purpose: This study examined the pedagogical experiences of former graduate teaching assistants following their teaching experiences at a youth development center. Method: A case study approach was utilized to investigate each participant case while a phenomenological approach was employed to analyze each case. The participants, Malik, Dante, and Ray, previously taught physical education at a youth development center as graduate teaching assistants. Results: The results of this study are presented as three cases centered on the participants and their experiences. The first case, "developing people from where they are, not where you want them to be . . ." (Malik) highlights the participants' appreciation of their students' culture and context. The second case, "resiliency to teach well regardless of circumstance or situation . . ." (Dante) features the participants' ability to teach diverse learners. The third case, "uphill battles . . . you cannot learn this in a textbook . . ." (Ray) features the challenges faced while teaching at the youth development center. Discussion: Consistencies across participants' experiences, the impact on their current careers, and implications for introducing culturally relevant and sustaining pedagogies via nontraditional settings are discussed.