Abstract This article elaborates on different modes of reflecting and on the significance of these differences for educational and educational-psychological practice. It contrasts exemplary materials from two research projects at schools where students share experiences of social exclusion, poor performance in mainstream educational settings, economic challenges, and family-related problems. These materials stem from my own ethnographic research that took place at an experimental vocational school in Germany in 2004 and 2005, and an a posteriori analysis of a school project that took place at the Woodrow Wilson High School in Long Beach, California from 1994 to 1998. Echoing Foucault as well as Vygotsky, the article demonstrates how diaries and narrations by young women written in different educational contexts promoted different forms of communication between teachers and students as well as qualitatively distinct modes of reflection. The analysis advances received scholarship by differentiating between introspection about oneself and reflection on the societal relations within which one is positioned. The focus on marginalized populations strengthens the argument by virtue of addressing challenging cases where this second kind of reflection is even more critical to one's development.