The Zhuangzi, a 4th century BCE Chinese text, is optimistic about life unrestrained by entrenched values. This paper contributes to existing debates on Zhuangzian freedom in three ways. First, it reflects on how it is possible to enjoy the freedom envisaged in the Zhuangzi. Many discussions welcome the Zhuangzi’s picture of release from life shaped by canonical visions, without also giving thought to life without these driving visions. Consider this scenario: in a world with limitless possibilities, would it not be (...) fraught, not knowing how to interpret situations? I suggest that freedom in the Zhuangzi is possible only if one succeeds in reorienting herself to the new ‘normal’. Second, I introduce and develop the idea of working with constraints. This focuses on an agent's maximizing the fit between relevant conditions, on the one hand, and their capabilities, on the other. Finally, I propose that self-directed practice, an important expression of agency, is required for building capabilities that enable such freedom. I examine the idea of risk involved in these firsthand experiences, articulating an account of agency that sits at the heart of hard-won Zhuangzian freedom. (shrink)