This work is a self-study examining my positioning as a Grade 10 Essentials math teacher during one school semester. Using a framework that draws on Bandura’s (1995) notion of self-efficacy, Dweck’s (2000) ideas of growth mindset, and Costa and Kallick’s (2008) and Cuoco, Goldenberg, and Mark’s (1996) work on habits of mind and mathematical habits of mind, I sought to position myself and my teaching in a way that would increase my students’ sense of confidence and capability in mathematics. I used narrative inquiry (Clandinin and Connelly, 2000) and autobiographical narrative (Bullough & Pinnegar, 2001) as interpretive frames to re-tell the story of the semester. What I came to understand is that I need to operate with a positioning that is dynamic, open-minded, and rooted in the notions of care (Noddings, 2013) and expectation if I hope to nurture students who are not only confident and capable, but who also accept the key role they must play in growing as effective and responsible learners. Despite being rooted in a particular time and place, and with particular students, this story seeks to acknowledge the realities teachers face in an honest and hopeful manner.