This article explores details of research that examined how the personal backgrounds of educators connected with organizational contexts to inform teacher practice within the area of adult English language teaching. Using life history as a research methodology and basing research on a framework of teacher authenticity, the primary goal of this study was to examine the influence of individual teacher backgrounds and organizational contexts on the formation of individual teacher practices. This study revealed how a lack of job security and professional definition contributed to a sense of instability that permeated workplace situations, forming barriers to establishing teacher practices based on ideals of transformative learning and authenticity. Additionally, working conditions that favored organizational hierarchy over professional understanding and support in the way of unions or professional organizations led to further inquiry as to where this type of marginal teacher practice sits in the overall spectrum of educational professionalism and practice.