<p id="p00005">Entrepreneurship is an emotional journey that is companied with fear of failure. Fear of failure can be both an enemy and a friend. It has a dark side of discouraging entrepreneurs from carrying out entrepreneurial activities, and a bright side of motivating them to move forward. Despite mounting research on entrepreneurs' fear of failure, most studies focus on its inhibitory effect on entrepreneurial entry. Few studies pay attention to the facilitating role of fear of failure and how does it influence the key behaviors in the whole process of entrepreneurship. Based on the research gap, the study focuses on the following three research questions. (1) What induces entrepreneurs' fear of failure? (2) How does fear of failure affect entrepreneurial behavior? (3) What are the boundary conditions of fear of failure on entrepreneurial behavior? Following the core logic of Affective Events Theory, the study constructs the theoretical framework of 'entrepreneurial event * entrepreneur -- fear of failure -- entrepreneurial behavior', and tries to explore this complex concept together with the insights from practice. <p id="p00005">This study aims to achieve four research goals. First, we explore the dimensions and contents of fear of failure in entrepreneurship context. From Cognitive Appraisal Theory, fear of failure is an emotional state results from the appraisal of the threats and possibility of failure in a specific situation. We thus capture this concept from two dimensions: sources of threats and ways of appraisal. <p id="p00005">Second, we investigate the different antecedents of fear of failure and explore how does it evolve in the process of entrepreneurship. According to the assumption of Classical Stress Theory, emotion is shaped simultaneously by the objective event and individuals’ subjective interpretation. We thus focus on two important factors to address the antecedents, i.e. entrepreneurial events such as loss-relevant event and low-capability-relevant event, and characteristics of entrepreneurs, such as entrepreneurs’ passion and ways of regulatory focus. In terms of entrepreneurial events, we propose that loss-relevant event and low-capability-relevant event positively affect fear of failure. In terms of entrepreneurs’ characteristics, we propose obsessive passion and prevention focus induce fear of failure, while harmonious passion and promotion focus inhibit fear of failure. <p id="p00005">Last but not least, we clarify how fear of failure relates to key entrepreneurial behavior. Existing studies had insufficient attention on the functional role of fear of failure. Endeavoring to start filling in this gap, this paper expounds three different effects of fear of failure on entrepreneurial behavior: incentive, inhibition and repression, looking at both the bright side and dark side of fear of failure. We further disentangle the boundary conditions of the relationship between fear of failure and entrepreneurial behaviors. In the micro level, when entrepreneurs get emotional support, the incentive effect of fear of failure on entrepreneurial behavior would be reinforced. When entrepreneurs get functional support, the inhibition and repression effect of fear of failure on entrepreneurial behavior would be mitigated. In the macro level, when the institutional environment is friendly and the cultural environment is more failure tolerant, the incentive effect of failure fear on entrepreneurial behavior will be increased and the inhibitory effect of failure fear on entrepreneurial behavior will be reduced. <p id="p00005">This study contributes to an emerging strand of literature on “entrepreneurial fear of failure” by looking deeply into the dimensions of this concept. It also offers novel perspective to understand entrepreneurial behavior and entrepreneurial psychology by taking account into the functional role of fear of failure. The present research not only expands the application scope and applicable situation of fear of failure, but also enriches the Cognitive Appraisal Theory of Emotion, Affective Events Theory and Classical Stress Theory. It also tries to shed light on practice by accumulating knowledge on entrepreneurial education and offer suggestions for policy makers on managing entrepreneurial failure.