This study aims to discuss the writing of dilemma in Chun-Ming Huang’s works and the ways the characters handle the difficulties. Hung showed his cares for90 people, society and nature in every one of his works, from The Child of an Ashman (1956) to A Pocket Watch (2008). The present study will focus on the writing of dilemma. Based on sociology, psychology and novel theories, the research will explore the purpose and meaning of the writing of dilemma. After a brief introduction, Chapter Two, Three and Four analyze three major dilemmas. The characteristics struggling because of insufficiency of materials, lack of value of life and absence of family members are under discussion in the first part, “Personal Difficulties”. Second, “Social Difficulties” describes how traditional culture was forced to fade away because of the changes in industrial structure led by economic colonization. Third, in terms of nature predicament, Huang thought it was the people that caused a lot of damage to ecological environment. He suggested people should respect the mother earth. In Chapter Five, the researcher talked about the ways Huang organized the dilemma and the rhetoric he employed in the novels. He stressed the impacts on the characters by reversing the conflict. He also showed the way the characters felt with their monologue. In terms of the rhetoric, both the dilemma and the affliction were intensified by symbols and contrasts. In Chapter Six, the researcher addressed how characters faced the difficulties and how they dealt with the problems. Because of poverty and innocence, the characters were used to blaming the disasters on the fate. However, no matter they gave up on fate or not, they kept walking with persistence. Their characteristics changed with time. Three common ways they fought with fate are as follow: to make a breakthrough, to bear up under affliction and to struggle for living. In the process of dealing with problems, they showed admiring attitudes towards lives despite being despised. Huang’s purpose of dilemma of writing is to solve the problems. “Children” are the keys to the questions. The rebirth of land is only possible when we make the next generation strong-minded. The only way to turn a dark night into the bright future is to consolidate the strength of people to guard our home, our land. This is the ultimate goal expressed in each of Huang’s works. The conclusion of the study was summarized in Chapter Seven. So were the suggestions for future research.