Social equilibriums can be both positively and negatively affected through the actions of social enterprises and social entrepreneurs and have both intended and unintended consequences. Many learners have considered only the light, or positive, viewpoint of social enterprise and social entrepreneurship. There are also potential dark aspects. In our increasingly ‘woke’ world, it is critical that we spur discussion of both light and dark issues. To deepen critical thinking about the implications of giving to ‘do good’, learners should consider potential dark motivations to increase the social enterprise’s competitive advantage through ‘green-washing’ tactics which could create dynamics of dependency, unneeded/unwanted assistance, or the disruption of local economies. The participants in the exercise experience the consequences of their decisions along with debrief opportunities for dark-light language. The authors provide a suggested pre-exercise reading assignment to prepare learners, the exercise and debrief guidance.