This article explores the experiences of a humanities graduate after leaving the academy. The author considers her own education in light of the historical changes in South Africa's education system. The article is a personal account of the questions and challenges encountered in choosing a humanities degree in a context where a tertiary education is crucial for future opportunities. The article explores life as a teacher in an education system that is assessment-driven and seems to sacrifice critical thinking. The article also considers the future of the humanities in a political and economic climate that highlights degrees directly linked to engineering and commerce.