A key characteristic of entrepreneurship is that it involves proactivity. Yet, the majority of the studies focus on the positive outcomes of proactivity and its less desirable consequences on individual-level (i.e., personal) outcomes have been understudied. The relevance of potential negative outcomes of behaving proactively is particularly relevant for entrepreneurs, who are always a bit more proactive than the general working population. Entrepreneurs often operate in highly uncertain environments and must continually push themselves to act proactively. The pressure to remain proactive in such settings could potentially increase stress, reduce well-being, and strain resources, making entrepreneurship particularly susceptible to the darker side of proactivity. The present study adopts a qualitative approach and integrates the resource drain theory with cybernetic control theory to show that proactive behaviour can deplete personal resources (e.g., time, money) under certain conditions. Our results revealed that “decision-making biases” and “distorted discrepancy-reducing strategies” act as boundary conditions that drive individuals to persist in proactive behaviour. Results further demonstrate that entrepreneurs’ proactive behaviour can lead to outcomes such as “emotional costs of persistence” and “resource depletion”. The study broadens the current understanding of proactive behaviour by shifting the attention from the traditionally emphasised positive firm-level outcomes to a more comprehensive understanding that includes unintended individual-level outcomes. Keywords: Proactive behaviour; dark side of proactivity; individual-level outcomes