A vast body of research has indicated that individuals with higher statistical numeracy, in comparison to individuals with lower statistical numeracy, make superior decisions by employing more deliberative processes leading to selecting options with the highest expected value (EV). However, it is not feasible to deliberate every time we make a choice due to cognitive and environmental constraints. In one simulation study and three well-powered, fully-incentivized empirical studies using the decision-from-experience task, we identified conditions where recurring suboptimal choices were more rewarding than a normatively superior strategy. That is, even if individual choices in isolation are considered suboptimal in light of the EV maximization principle, individuals with higher numeracy can adapt their decision strategy in accordance with changes in the task structure, and make faster suboptimal (or random in terms of EV maximization) decisions that result in overall superior performance (e.g., earning more money). We found that individuals who maximized EV without time constraints accumulated higher total gain. However, the trend reversed in the following two studies. Participants who made more suboptimal choices, under time constraints, earned more money than those who spent more time maximizing EV. Importantly, we found that more numerate individuals made significant adjustments to their meta-cognitive decision processes and made more quick suboptimal choices resulting in better overall earnings than less numerate individuals. Finally, our results also indicate that more numerate individuals are better at identifying the changes in the task structure and are more rational in their use of cognitive and environmental resources.