This article first reveals the comparability of the classical Western idea of leisure and Chuang Tzu's idea of hsiao-yao. Next, both the metaphysical origin and the etymological origin of hsiao-yao are traced. Then, Chuang Tzu's ideal of hsiao-yao and some relevant ideas are discussed. This article elaborates much on Chuang Tzu's philosophy of how to attain hsiao-yao, an ideal of reaching the ultimate state of being, the absolute freedom and true happiness.