Medical doctor and engineer are highly esteemed STEM professions. This study investigates academic and motivational characteristics of a sample of high school students in Thailand who aspire to become medical doctors or engineers. We used logistic regression to compare maths performance, gender typicality, gender contentedness, and maths and physics self-concepts among students with aspirations for these two professions. We found that high levels of felt gender contentedness in men had positive association with aspirations for engineering irrespective of the levels of maths or physics self-concept. We found that high levels of felt gender contentedness combined with high levels of maths or physics self-concept in women had positive associations with aspirations to become a medical doctor. These findings are evidence that student views of self are associated with uneven gendered patterns in career aspirations and have implications for the potential for future participation.