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There is a growing interest on how critical perspectives can help us understand family businesses. Current literature suggests that critical reflection is needed in aspects such as conflict, fear, and emotions. In this chapter, we argue that the use of a critical perspective illuminates the intricate complexities of family business behavior and that a critical discussion around fear, which is conceptualized as both an inhibitor and a motivator for business, plays a significant role in the dark side of family business. To advance understanding, we review recent conversations that can help us understand better the role of fear; how does this impact on resilience? And, how do feelings and emotions impact family firms? In our review, we argue that perspectives that focus on specific tangible resources (e.g. financial) are limited to explain how families in business may deal with fear. A critical perspective suggests that three areas merit further attention: fear of failure, effects of failure, and the intersection between entrepreneurial learning and the effects of fear in the dark side of family businesses. By contextualizing critical approaches, we provide insight for researchers, policymakers, and those operating family businesses alike.