Human behavioral change is necessary if we wish to evolve into a more sustainable human society, but change is hard, especially given that many people equate environmentalism with personal sacrifice. This paper highlights a semester-long assignment in which undergraduate students examined five behaviors that claim to increase happiness with minimal ecological footprints. We used mixed methods to analyze students' self-reported positive and negative affect scores before and after completing each of the five activities, along with descriptions of the carbon footprint of each activity and student self-reflections on whether each challenge promoted "sustainability". Results indicated that students' positive affect increased with each activity, while negative affect decreased. Student reflections indicated that engagement with systems thinking can be used to examine the relationship between their own well-being and the ecological outcomes of each of their chosen activities, as well as alternatives that would decrease their footprint. In final reflections, 85% of students stated that they would promote these five behaviors among the general public to enhance sustainability efforts. We discuss using the Sustainable Well-being Challenge as a tool to promote behaviors that support both human and ecological well-being.