Drawing inspiration from Parker Palmer and John Dewey, this essay explores the author's journey of learning to connect with his ninth-grade students in a summer study skills class. Using the metaphor of an "undercarriage," the author reflects on how he strengthened his capacity to endure classroom challenges. Through experimentation with new approaches, the author discovers a "third way" between rigid control and passive acceptance, ultimately reframing his teaching identity. The author concludes that such identity work cannot be achieved in isolation but requires the support of colleagues, particularly in times of struggle. The author's experience offers insights into the challenges educators may face when striving to create more authentic and effective learning environments.