While visual perception and aesthetics are fascinating topics, attempts to merge them with an understanding of design is frustrating. Explanations of optical illusions or gestalt principles in design seem too basic without concrete examples or practical applications. These principles could be represented in a more design-oriented manner rather than with solid shapes and simple figure-ground relations. M.Y.R.T. (My Year of Research and Things) is a research project that explores the relationship between perception and meaning through three pathways of form, context, and medium. The experiments consist of rock illustrations which made an interactive poster, a book, and several medium iterations of the same conversation. The rock illustrations explore ideas from studies outlining how individuals perceive art in different “steps” relating to the visual and semantic features. The layers of illustrations came together in an interactive poster where the viewer discovers the full form through tearing. The book, based on the famous Ebbinghaus Illusion, shows that an object reads differently based on contexts. Amidst Covid-19 and social distancing, I began considering what personal interventions or manipulations could be made to alter our perception in digital spaces. I represented a video conversation with a friend three different ways: a rotoscope animation, a magazine interview, and a questionnaire form. Perceived meaning changes based on design decisions around form, context, and medium. If exercises for design students provided simple excerpts relating to perceptual psychology, perhaps actively making a wide variety of iterations in response to how those readings might relate to design would reveal that iteration is not just to find a design solution, but a means of answering or beginning to solve larger questions.