We evaluate how features of the digital environment free or constrain the self. Based on the current empirical literature, we argue that modern technological features, such as predictive algorithms and tracking tools, pose four potential obstacles to the freedom of the self: lack of privacy and anonymity, (dis)embodiment and entrenchment of social hierarchy, changes to memory and cognition, and behavioral reinforcement coupled with reduced randomness. Comparing these constraints on the self to the freedom promised by earlier digital environments suggests that digital reality can be designed in more freeing ways. We describe how people reassert personal agency in the face of the digital environment’s constraints and provide avenues for future research regarding technology’s influence on the self.