A new age of significance and opportunity for Information Systems (IS) is upon us driven by current developments in the use of digital artifacts. In this paper we endeavor to make sense of contemporary IS, as well as possible future directions of IS, by bringing together the notions of complexity and activity within two theoretical frameworks, namely the Cynefin framework and contemporary uses of Activity Theory. We describe activity as a holistic unit of analysis within the Complicated and Complex Domains of the Cynefin framework. This will enable us to make sense of tool-mediated IS activities in those Domains. Our proposed research philosophy blends these frameworks to support new thinking about IS that impacts on our choices of research methods, the way we apply them and the way we modify them as the world we study evolves into an uncertain future context.