In this paper, I am concerned with the ways in which one is habituated into looking at students through Descriptive Inquiry as meditation. In exploring this question, I trace my own journey from student to teacher educator--marking the ways in which Patricia Carini's (2000) means of attending with care influenced and marked my journey at every turn. In sharing my journey in narrative form, I first showcase an alternative habituation to looking at students--rare in the current educational context--and then articulate how I seek to influence the habitus in which new teachers are educated.