In the discipline of IR, a growing number of academics work with artists, designers, architects, and filmmakers to explore a range of global political, economic, and security challenges. At the same time, there has been a concern—made powerfully by Dan Öberg—that there is a danger of what he terms “transgressive creativity” in the way that new approaches and methods are being used to respond to security challenges, especially in a military context. In this essay, I explore how the problem of this “transgressive creativity” is a concern shared by two groups working on the problems of security, war, technology, economy, and politics: critical designers and military designers (or the group that is becoming known as the Archipelago of Design). While the objectives of both communities are different, they both share a view that a sense of openness to collaboration is essential to go beyond traditional institutional approaches in order to make sense of complex and uncertain futures in a time of technological acceleration and geopolitical change. The essay concludes that we should be vigilant to the problems of transgressive creativity that Öberg alerts us to, but we also need to broaden the research agenda to understand how creative techniques are being used by a variety of actors and organizations to address the problems of international politics; academics in IR also need to see whether the “openness” to collaboration has broader disciplinary and methodological implications for researchers.