This article investigates the dynamics of socio-ecological systems (SESs) unsustainability. By adopting a theoretical standpoint grounded in systems’ theory, the analysis shows how SESs’ teleology (or final cause) is of the utmost relevance for understanding unsustainability and how it is pivotal for envisioning possible evolutionary trajectories towards sustainability. Building on the contributions of both system and social scientists, the study argues that SES’s teleology is determined by dominant social ontologies that require a dialectical lens to be properly dealt with. The article therefore proposes the adoption of the adaptive cycle heuristic complemented by an historical-geographical approach based on world-ecology theory as a means to dynamically model of SESs’ behaviour. Such a perspective allows for the direct comparison between the four stages of the panarchy cycle (reorganization, exploitation, conservation, and release) and the four stages theorized by the world-ecology dialectics (expansion, appropriation, capitalization, crisis). In conclusion, the article claims that both system and social scientists would benefit from including in their analysis concepts and definitions from the other field, since both provide valuable insights about SESs' processes of change and both are necessary to envision transition pathways towards sustainability.