Like many of the Taiwanese gentry in the Japanese era, Kuo's father hoped his son would study medicine. To that end, he shipped Chih-yuan off to Japan, where he tested into Tokyo's Kinjo Gakuen High School as a second-year student.
和一般日治時的台灣仕紳一樣，一心希望他學醫的父親，15 歲時就將他送到日本，通過轉學考試進入東京錦城學園中學二年級就讀。