This article presents the findings of a historically-informed comparative study that juxtaposes the lives of three missionary educators in China in the early 20th century with three Christian educators in China today. Data sources included hundreds of letters from the women written in China to their families and friends over several decades and transcripts of over a dozen interviews. Wenger’s social theory of identity formation was used to analyze the data and address the questions of why they went to China, the intended and actual results, and the impact it had on the women and their identity construction. The findings show that although there were major differences across the two centuries, as was expected, there were surprisingly many similarities among the individual teachers, as are noted in the common communities of practice that emerged: “educator,” “missionary,” “gender advocate,” “Chinese advocate,” “leader,” and “learner.”