Young drivers are more likely to continue driving when experiencing signs of sleepiness and are over-represented in sleep-related crashes. Adolescence and early adulthood are characterised by comparatively poor executive functioning, and while previous research has demonstrated a link between poor executive functions and several risky driving behaviours, the relationship with sleepy driving is not well understood. Accordingly, the first aim of the current study was to examine the association between executive functions and experiencing the signs of driver sleepiness in a sample of young adult drivers. Additionally, young drivers who have less experience with driving while sleepy, may attribute less importance to the signs of sleepiness as an indicator of underlying sleepiness level. To test this assumption (aim two), the impact of experiencing signs of sleepiness on perceptions of the importance of those signs was examined. Participants included 118 young adults aged between 17 and 25 years, who completed an online survey measuring experiences with the signs of sleepiness while driving, executive functions, and demographic characteristics. This sample of young adults reported having considerable experience with several signs of sleepiness (i.e., yawning, mind wandering, and difficulty keeping eyes while driving). A linear regression analysis found that the demographic variables of age and hours driven per week, as well as the executive function constructs of organization, strategic planning, and impulse control were associated with experiencing signs or sleepiness. Moreover, having experienced more signs of sleepiness was associated with an increased likelihood in rating those signs as important indicators of sleepiness. The current findings suggest both that several high-level cognitive processes as well as levels of experience with driving when experiencing signs of sleepiness contribute to young peoples’ sleepy driving.