This study attempts to discuss the history of Master Cheng Yen’s exposure to Buddhism and the journey of becoming a nun, by which to illustrate the Bodhisattva’s image of Master half a century ago and leave behind a cultivation paradigm for the future generations. The paper focuses on the combing of the historical context by the methods of documents collection and analysis, supplemented by oral interviews. The main subjects include "the transition from grief to mercy", "the dilemma of filial piety and monasticism", "the choice between self-interest and altruism" and "the fusion of personal and long-lasting love". In order to explore Master Cheng Yen’s early years of cultivation, one must look back at his early life story, get a glimpse of the whole process of his enlightenment, and outline his personal asceticism and religious practice, and how to overcome all the difficulties to establish Tzu Chi Foundation eventually. When Master faced pains and accidents, what was the significance of religious belief in his life? How did he turn personal love to great love, transforming the "sorrow" of the sudden death of his father to the "mercy vows" of saving all the people in need? Why did he stop pursuing self-liberation and choose to take the responsibility to purify all the people’s hearts? How did these changes appear in his heart? Between reality and ideals, he resolutely chose to become a nun, how did he deal with the family affection and persuade himself? Along the way, what was the key points of determining his way to Bodhisattva? All these questions are worthy of discussion to analyze Master Cheng Yen's transition process from self-cultivation to public preaching. As stated in the conclusion in the final chapter, the four keywords summarized in the paper: suffering, Dharma, benevolence and emotion, can be used as annotations on Master Cheng Yen's early spiritual cultivation. His comprehension of "suffering" reinforces his pursuit of the value of life and the truth; his belief in "Dharma" supports him practicing the vows along the way; his inner benevolence affects massive love of the public to relief the suffering; his broad "emotion" and unselfish mind teaches people to be compassionate and wise. In short, Master Cheng Yen, with his compassionate heart, corresponds to the deep wisdom of the Bodhisattva, and leads everyone to practice Bodhisattva’s deeds to accumulate wisdom and blessings. Hope the study results of this paper to provide references for domestic and foreign academic circles, and stimulate more researchers to pay attention to related topics.