Charmaine is an engineer, business consultant, and—most recently—a teacher. Placed at her sons’ high school, she experienced education through many different lenses: as both parent and teacher, she taught her kids’ friends, and she taught her friends’ kids. She discovered what it was like to be responsible for more than 100 other students each day. She learned that feedback doesn’t have to be judgment; if used properly, it helps people to expand their worlds. But, most importantly, she saw how blaming strategies—while meant with the best of intentions—risk enabling helplessness by giving students reasons not to try. That experience transformed how she viewed her role as a parent. Rather than being the consumer (e.g., being critical of how schools met the needs of her own family), she became more of a long-term investor (e.g., seeing the value in giving everyone in the parent-teacher-environment triad support). With a sense of humility, she listened more, asked questions before judging, focused on empathy and problem-solving, and, most of all, encouraged interactions to support her children in building relationships that mattered. Over time, she began to question the general narrative surrounding schools. Problems framed as permanent and pervasive (e.g., schools kill creativity) were more likely to erode the psychological safety required to support learning compared to framing that was more temporary and specific (e.g., when schools do X, some students with Y may experience Z). Charmaine has come to believe there is a need to bring a sense of humanity and accountability back into the classroom where the norm is that everyone (students, teachers, and parents) makes mistakes, and everyone can feel vulnerable enough to learn. Through the development of dialogues that use processes for improvement rather than categories for judgment, Charmaine is committed to writing a book and a curriculum that will teach people the broader perspective of how their individual roles fit into the integrated whole of our learning communities, where all of us do matter and all of our messages count.