Looking back on the celebrated literati throughout Chinese history, quite a few are frustrated on their journeys into government offices or blighted in their lives. Among them, Su Shi is the only one, who undergoes failures most of his life, repeatedly suffering distress; however, he sees them as credits, taking easy the adversity in life by mocking and making fun of himself. Equipped with resilience, he comes to realize wise life lessons: staying bighearted, liberal, and optimistic towards things. Nonetheless, his way of thinking is not attained by overnight inspiration, but by years of frustrations at the Song court before he is exiled to Huangzhou, all of which contribute to his character and philosophy of life when agony and hardships confront him. Being fearless, and living out the true meaning of life, Su Shi undoubtedly is a mentor to those modern people who, succumb to frustrations and lose themselves at the crossroads of life. Hence, this thesis is mainly to study what has happened to Su Shi in the government office before sent into banishment, from which the budding of his character and philosophy of life is thus inferred.