Form the perspective of life history, this paper aims to explore how individuals face education and career choices presented at each stage since elementary schools in their lives, factors and conditions that influence such choices, as well as how and why the influence of these factors waxes or wanes. Thirty-seven samples were drawn from over 20,000 students who had previously participated in the ”Taiwan Education Panel Survey” (TEPS). Twenty-six were interviewed in 2008, while 13 follow-up and the other 11 new interviews were conducted in 2009. By employing the concepts of socialization, family capital, and stratification in education, this paper analyzes how the youth who were born in the mid-1980s in Taiwan engage in educational and career choices.