Children’s occupational aspirations begin forming at an early age and there are multiple social, educational, and experiential factors that may affect them. These aspirations are still poorly understood in the context of presumptive labour markets, however. This study aimed to elucidate the frequency, influences, and rationale regarding the occupational ambitions of children attending grades 1–5 in elementary schools in a region of Sweden, and to compare these to expected labour market demands when they might enter the workforce. The internationally established Drawing the Future method was employed to obtain answers from 1832 pupils, who drew 409 unique occupations within about one third of all possible standard occupational classification categories for Sweden. Only six categories contained an occupation drawn by more than 4% of pupils. The drawn occupations would, if realized, lead to an exacerbation of the ten occupations predicted to have the greatest undersupply, and only alleviate a minority of the future needs of the labor market. There was a considerable absence of STEM-related occupations, and gender differences among the drawn ambitions were large. Media and online sources were stated as the most common sources of knowledge about the drawn occupations, while schools accounted for only 6%. Pupils heavily emphasized experiential factors such as “having fun” and doing “cool” and “exciting” things as a rationale for their chosen occupational ambitions. A large majority of pupils believed the labor market would present many opportunities for them, that schooling was important to achieve success in these markets, and that both genders could undertake similar occupations. Interest in continuing to post-secondary education was considerable. There were few differences among pupils with Swedish backgrounds and those with foreign backgrounds. Future research should address longitudinal changes in both ambitions and influences, as well as the effects of information-based interventions on labor market needs and demands.