Purpose: Our research unpacks transformative learning through learning-with the city and the agency of encounters. We exemplify how post-human education methodologies can make students sensitive to rhythms beyond their own, helping them to get to know Earth as more than a backdrop for human activity. Approach: Walking the historical shoreline of Helsinki challenges rigid notions of a landscape and collapses the past with the present and future, revealing the porousness of the city and self. Findings: Engagement with landscape remnants makes everyday transformations and entanglements tangible, engendering thinking-with the city. Research implications: Post-human approaches to transformative learning give valuable insights into how learning is non-linear, non-representational, and takes place through meaningful encounters with the world Practical implications: Post-human methodologies lay the groundwork for how experiments could be developed by social science educators in different localities, e.g., having students walk along a railway refusing to give way for an ever-growing city.