Alternative behavioral strategies typically differ in their associated risks, meaning that a different variance in fitness-related outcomes characterizes each behavior. Understanding how selection acts on risk preference is crucial to interpreting and predicting behavior. Despite much research, most theoretical frameworks have been laid out as optimization problems from the individual’s perspective, and the influence of population dynamics has been underappreciated. We use agent-based simulations that implement competition between two simple behavioral strategies to illuminate effects of population dynamics on risk-taking. We explore the effects of inter-generational reproduction dynamics, population size, the number of decisions throughout an individual’s life, and simple alternate distributions of risk. We find that these factors, very often ignored in empirical and theoretical studies of behavior, can have significant and non-intuitive impacts on the selection of alternative behavioral strategies. Our results demonstrate that simple rules regarding predicted risk preference do not hold across the complete range of each of the factors we studied; we propose intuitive interpretations for the dynamics within each regime. We suggest that studies of behavioral strategies should explicitly take into account the species’ life history and the ecological context in which selection acted on the risk-related behavior of the organism of interest.