Running errands is a common task for most people and involves navigating to multiple destinations within a given timeframe. Under and overestimating the amount of time needed to complete a set of errands may result in costs (e.g., running late to a meeting or having excess time to fill). However, such estimates are often made in the face of uncertainty. For example, long lines at the grocery store, a traffic jam caused by an accident, or poor spatial knowledge about the environment can hinder our ability to estimate the time to run errands accurately. In this line of research we investigate individual differences in errand running ability, risky decision-making when estimating time to complete errands, and the relationship between spatial reasoning skills and errand running ability.