Self-study takes various forms, one of which is autobiographical narrative inquiry. It offers insights into understanding the private worlds of human beings and provides insider perspectives about phenomena. This chapter reports on a comparative self-study based on the autobiographical narratives of the two authors, who both played multiple roles in shadow education (i.e., private tutoring) as tutee, tutor, entrepreneur, and researcher in different contexts (Hong Kong and Mainland China) and at different stages. In this chapter, we present our own autobiographical narratives, mapping dynamic features of shadow education along with our lived experiences. Then we juxtapose our voices and alternate between our stories to compare critically our learning, tutoring, and researching experiences in this industry. Finally, we reflect on the significance of this comparative self-study.