Path-dependency is an unfortunate behavior (Choi, 2011). Although researchers acknowledge the omnipresent nature of path-dependent behavior (Gruber, 2010), especially in innovation processes and organizational developments (Mishina et al., 2012; Thrane et al., 2010), little research on understanding path-dependency in the context of entrepreneurial and managerial decision-making was carried out so far. Therefore, understanding antecedents and environmental conditions is the main focus of our research. This paper studies path-dependent behavior when selecting and combining means to solve entrepreneurial and managerial problems under different conditions. We focus on entrepreneurial self-efficacy (McGee et al., 2009) as its subdimensions can be utilized to distinguish entrepreneurs from managers (Chen et al., 1998). To account for several environmental conditions, we designed a unique experimental questionnaire inducing four specific scenarios in temporal order. We hypothesize that path-dependency can be burst in specific situations.