Painting Round Objects with Straight Tools is an observational painting experiment I devised specifically to frustrate my Painting 1 students. Students are tasked with painting a still life composed of oranges and grapefruit set in draped fabric, using only straight edged palette knives. What initially seems like an exercise in futility is actually a demanding approach to turning the form with color and value as the available painting tools are restricted. This is a difficult task designed to frustrate familiar and easy approaches to painting. It forces students to think differently about their approach while demanding they keep their decision making rigorous and front of mind. It is especially helpful in getting students out of their comfort zones in order to open them up to new possibilities of creative thinking as well as to breakthroughs in creative making. When all of the paintings were completed students were then prompted to collaborate on developing a group installation in which the goal was to make the stripes of the painting “make sense” as if it were one continuous piece of fabric (or as close to it as possible).