In this article we describe our engagement in self-study as part of an examination of design-based research for education. We focus on graduate-level online teacher education as an example of how self-study provided a means of examining deeply our teaching and our roles as teacher and designer in the learning environment. We posit that online learning environments are particularly well suited for self-study to enhance design perspectives because the interactions between teacher and students are informed by personal context and mediated by technological tools. The graduate students in our courses were teacher leaders in literacy or mathematics who were learning how to support professional development for other teachers. Throughout our self-study research we found ourselves drawing upon our previous design research experiences, which aided our ability to engage in self-study: We were part of the classroom system, focusing on our roles within the teaching and learning process as designers of the online learning environment. Three key design principles resulted from our self-study process: focusing on systems of learning and teaching, designing pedagogical tools and products, and using iterative processes. Engaging in self-study enhanced our understanding and implementation of synchronous online instruction, particularly regarding our use of technological tools to enhance student learning and support learning communities.