I explore conceptions of happiness in classical Chinese philosophers Mengzi and Zhuangzi. In choosing to frame my question with the word ‘happiness’, I am guided by the desire to draw some comparative lessons for Western philosophy. ‘Happiness’ has been a central concept in Western ethics, and especially in Aristotelian and utilitarian ethics. The early Chinese concept most relevant to discussion of Mengzi and Zhuangzi concerns a specific form of happiness designated by the word le, which is best rendered as ‘contentment’. For both Mengzi and Zhuangzi, there is a reflective dimension of happiness that consists in acceptance of the inevitable transformations of life and death, though these two thinkers chart very different paths to such acceptance. Mengzi holds that it lies in identification with a moral cause much larger than the self. Zhuangzi is profoundly skeptical about the viability of such a path to contentment. He instead offers identification with a world that transcends human good and evil, and a way to live in the present that can be deeply satisfying. One interesting outcome of both their discussions of achieving happiness is that both come to question the importance of happiness as a personal goal.