Exponents of critical thinking emphasize the teaching of skills and dispositions for scrutinizing the assumptions, reasoning, and evidence brought to bear on an issue by others and by oneself. In short, they promote thinking about thinking. But how do students come to see where there are issues to be opened up and identify them without relying on some authority? The current form of my evolving "answer" is that people need support to grapple with inevitable tensions in personal and intellectual development—support to undertake journeys that involve risk, open up questions, create more experiences than can be integrated at first sight, require support, and yield personal change. In this essay I present five passages in a pedagogical journey that has led from teaching undergraduate science-in-society courses to running a graduate program in critical thinking and reflective practice for teachers and other mid-career professionals. I have shaped these passages to expose some of my conceptual and practical struggles in learning to decenter pedagogy and to provide space and support for students to develop as critical thinkers. The key challenge I highlight is of helping people make knowledge and practice from insights and experience that they are not prepared, at first, to acknowledge. In a self-exemplifying style, each passage raises some questions for further inquiry or discussion. My hope is that the essay as a whole stimulates readers to grapple with issues they were not aware they faced and to generate questions beyond those I present.