A good student and ambitious, Si Tiau-hui, like most promising young men of his day, aspired to become a medical doctor- the pinnacle profession of Taiwan's society at the time. Later he began to realize that perhaps this was not the way he wanted to serve society. His mother had expected him become a medical doctor, but he yearned to learn more outside of the limited higher education opportunities available in Taiwan. Fortunately his family had the means to send him to Waseda University (in Tokyo, Japan) where he obtained a degree in political science and economics. This was against his family's expectations; they expected him to study something practical, that would lead to a stable career, perhaps in the field of business since he could not be persuaded to become a medical doctor. Once Si Tiau-hui was at Waseda, the worlds of literature, arts, music, world history, and political theory opened up for him in a way that wouldn't have been possible in Taiwan.
He saw Japan as a rampant imperialist force that needed to be reigned in. Communism was an ideal form of socialism which led him to go to China in the pursuit of understanding. With high ideals he set off for China upon graduating from Waseda in 1942- to work with the Chinese Communists in the resistance against Japanese imperialism.
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