Zhang Shigu was a school-teacher in an public elementary school in Xinzhu prefecture during the 1910s. This article explores Zhang Shigu's biography and his career development as a case study to examine the institutional channels of upward social mobility offered by the Japanese colonial government. Zhang's career development also provides a model for understanding the ”ladder of success” of Taiwanese local elites within the colonial system. Zhang was in school when Japan began its colonial rule, and thus belonged to the first generation of local elites who were educated in the new curriculum. Other than becoming a doctor, a good option for the new educated local elites before 1910s was to attend teacher's college and return home to become a school teacher after graduation. But by the 1910s, there emerged new opportunities in many social sectors as Taiwan developed. Many young school-teachers left their teaching jobs, followed these new opportunities, and changed their careers. Zhang followed this track and left his teaching position in 1920. He then joined the local administration and was in charge of village affairs. Later on he invested in business and developed a successful career in commerce, benefitting from monopoly rights granted by the colonial government. The Japanese colonial government granted such benefits to those who had influence to gain their cooperation. Looking into the different choices Zhang made on his path of upward social mobility, it is clear that the ladder of success he was able to climb was provided by the changing colonial policies at various moments, even while it was also limited to local society under the restrictions established by colonial rule.