Rapidly changing environmental and social conditions require thinking outside boxes and pioneering unconventional practices. But not just any innovative line of thought or novel practice will be a positive response to the major problems of our time; some might make things worse. How can we recognize unconventionality that orients us toward being more sustainable rather than less? One approach is to attend to complexity. Conventional thinking – that which is embedded throughout culture and is generally accepted – sees complexity as a characteristic of the world (earth systems are complex; society is complex) and as a problem to be simplified, solved, or avoided. We can see conventional thinking as a “simplifying eye” on the world; developing a new “complex eye” doesn’t detract from science but through synthesis leads to a kind of depth perception that we now lack. The work of philosopher Paul Cilliers on critical complexity is a guide to imagining a dual perspective in which simplifying (e.g., reducing, objectifying) and attending to complexity (e.g., relational thinking) work together. For example, Cilliers’ insights into organization direct our attention to organizational boundaries: why they exist and why they are as they are. The dominance of discipline-bounded priorities in academia inhibits complexity thinking; shifting to transdisciplinarity by orienting ourselves toward real-world issues can better foreground sustainability in research and teaching. More encompassing theories of complexity include complicity – the acknowledgement and discussion of how human perspectives and choices are inevitably entangled with nominally objective science. I describe designing a course on quantitative analysis of earth systems data for undergraduate and M.S. students at West Chester University that is organized to reveal complicity while simultaneously teaching methods of exploratory data analysis needed by scientists. Attending to complexity and complicity in course design and pedagogy doesn’t replace but rather enhances traditional course objectives. These framings of complexity, transdisciplinarity, and complicity help us step “outside” unsustainable cultural assumptions to generate new worldviews.