For over 20 years I have been investigating interest-based learning and I first started on this path largely because of what Boxer seemed to afford students and their expressive needs in the classroom. In this brief essay, I reflect on my early observations of students’ interest- driven pursuits in Boxer and the research those observations have spurred, (Azevedo, 2006, 2011, 2013) and distill some key lessons from these experiences. In particular, I focus on how empowering students with a reconstructible computational medium such as Boxer can lead to humbling insights into our own learning and development as researchers and educators, as well as to larger questions regarding knowledge production and the work toward a socially just world.