The contribution of a balance of work and leisure to health and a sense of well-being is a common sense assumption in everyday knowledge as well as in occupational therapy. The impact of the organization and balance of occupations in daily life on health, adaptation, life satisfaction, and a sense of well-being are central issues in occupational science. One of occupational science’s potential contributions to society is the ability to provide understanding and insights that transcend common sense assumptions and everyday knowledge about occupations. This article will address, through a review of the literature, some of the limitations inherent in belief about a healthy balance of work and leisure. It will demonstrate how distinctions between work and leisure are culturally bound and perpetuate the assumption that they are dichotomous experiences. This dichotomy is shown to be a false one and must be transcended in order to explore the question of what is a healthy balance within daily life. This article concludes with consideration for occupational therapy research and practice that may arise from transcendence of the dichotomy of work and leisure.