South Korean society in the late 1990s was confronted with socio-economic setbacks and discursive turbulence concerning the quality of education being provided. It was at such a particular historical juncture of South Korean society that I conducted ethnographic research on homeschooling families. Based on field data collected from four homeschooling families, this article examines how lower middle-class families at first manifested their education fever in an unprecedented adoption of homeschooling, and then returned their children to school within the same socio-cultural context. Central to this article's analysis is what members of these middle-class families, especially children, experienced during the homeschooling period, and how parents negotiated their rationale for homeschooling and returning their children to school within contesting discourses (e.g., deschooling and neo-liberalism). As will be shown, despite experiencing difficulties in pursuing a self-fashioned education in a school-centered society, the families benefited from homeschooling in terms of acquiring "neo-liberal" mentalities for survival without risking their established socio-cultural status. As such, this article reconfirms the ambivalent characteristics of the alternative education movement in South Korea and its inevitable connection with the middle-class "habitus" embedded in the South Korean socio-cultural context.