This paper challenges the view that contentment leads to personal freedom and autonomy and argues for a relational and exercise concept of de facto freedom in the Zhuangzi 莊子. I first review influential interpretations of freedom in the Zhuangzi that equate freedom with contentment and nonfrustration, starting with Guo Xiang's 郭象 (d. 312 CE). By putting these interpretations in dialog with contemporary social philosophy (Christman, Meyers, Pettit, Elster, and Khader), I reflect on the two seminal problems of the psychologizing causal (...) and procedural approaches that allow the interpretation of freedom as contentment: the “happy slave” problem and the “sour grapes” problem. Proving this account of freedom inadequate, I argue for a different interpretation of freedom in the Zhuangzi that resembles a weakly substantive and constitutive account of freedom and autonomy in modern‐day social philosophy terms, such as Marina Oshana's. The theory of freedom that I analyze in the Zhuangzi, however, helps us correct the risk of material determinism of the constitutive account, offering a description of relational freedom and autonomy as constituted by socio‐material conditions but not determined by them. (shrink)