Teacher development does not stop when a degree is earned--at that point, it has barely taken flight. Real teacher growth happens when meaningful time and safe and authentic space are given to discussing and refining practice under the guidance of a pedagogically and contextually experienced mentor. Here, one teacher leader recounts her purposeful transition from the classroom to a nearly full-time mentoring role at an urban charter high school. Through a review of, and reflection on, field notes from these first few years of mentoring, she sheds light on the challenges and victories of not just those she mentored but of learning to push for a more practical and personal vision of teaching and learning.