White-collar workers around the world are reconfiguring their ways of working. Some have found their way out, performing office work outdoors, through walk-and-talks, outdoor meetings, or reading sessions. Working outdoors has proved both invigorating and challenging. This qualitative interview study aims to develop a conceptual framework concerning the implications of white-collar workers incorporating the outdoors into their everyday work life. Applying a constructivist grounded theory approach, 27 interviews with a total of 15 participants were systematically analyzed. Findings evolved around the following categories: practicing outdoor office work, challenging the taken-for-granted, enjoying freedom and disconnection, feeling connected and interdependent, promoting health and well-being, enhancing performance, and finally adding a dimension to work. These categories were worked into a conceptual model, building on the dynamic relationship between the practice of working outdoors on one hand, and how this challenges the system in which office work traditionally takes place on the other. Interviews reflected the profound learning process of the employees. Drawing on the concepts of free space and resonance, we demonstrate how performing office work outdoors may unlock a transformative potential by opening up connectedness and interdependence and contribute to a sustainable work life as well as overall sustainable development.