Su Shih, one of China's most significant scholars, lived his life under the shadow of two mutually opposing unfulfilled ambitions: to serve actively in the highest levels of central government, and to lead a life of quiet spiritual and physical cultivation with his brother, Su Ch'e. This tension is a major component in most of Su Shih's greatest literary writings, and is central to our understanding of the person and his works, and by extension, of the mid-Northern Sung political world. This paper follows the development of Su Shih's awareness, interpretation, and public expression of the details and implications of a dream he had in the last few month s of 1091, and the great impact it had on him in his later years. By observing the poet as he eventually works through this particular dream, it is possible to follow the development of an idea, along with its outward expression, of which at first even the poet himself may not have been aware. Such analysis can provide glimpses into hitherto unrevealed intimated levels of his mind. We are then able to observe firsthand the process of one of China's foremost thinkers as he resolves the pivotal, paradoxical problem of his life, which manifested itself in some of the greatest pieces of Chinese traditional literature. We see Su Shih gradually accept his inability to fulfill his political ambition, and finally embrace his goal of leading a secluded life of idyllic simplicity, and spiritual and physical cultivation.