This chapter is a historical analysis of the notion that good teaching is an inherent quality that draws on natural attributes of the indi­ vidual. In particular, I am interested in the effect that the popular meaning of the “naturally born teacher” had on nineteenth-and early twentieth-century women teachers as they first entered the oc­ cupation. By studying the journals of three nineteenth-century women teachers in New England and the student-teacher journal of a kindergarten teacher in Boston in 1904,1 analyze the way in which these women experienced an interior regulation of their work: in the privacy of their own home after class, they wrestled with their own personalities and perceived character flaws, struggling to re-create their own thoughts and feelings to fit the popular image of what they had been taught a good teacher should be. According to these women, a good teacher was not only one who acted in certain ways, but one who veritably was a certain kind of person.