Autoethnography is adopted as the procedure and orientation for this PhD study which aims to explore the cultural identity of the Chinese families and its influences on their children's mathematics learning. The purpose of this paper is two-fold. First, readers are invited to travel with the researcher a journey in which she explores her diasporic identity by engaging in the stories of others. This will be done by examining how her understanding of her own Chinese identity was challenged by those of the participants in the interviews. Second, through her experience and reflections, readers are provided with an insider's lens to understand some of the data collected in the interviews. Data are collected through interviews, journals, observations and fieldwork memos. As an autoethnographic study, it is not the aim of this thesis to provide a generalization of data. Rather, rich data sets which are partially contrastive and partially congruent to one another challenged the homogeneity of Chineseness. This paper discusses how the researcher uses her dual positionality to explore blurred boundaries between the observer and the observed, insider and outsider. It highlights how self is an important instrument in both the collection and analysis of data.