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 <SIC>offspring. I first review influential interpretations of freedom in the Zhuangzi that equate freedom with contentment and nonfrustration, starting with Guo Xiang's &(sic) (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.