The paper explores factors of importance for young people’s choice of upper secondary education and for their future life, from a student perspective. The paper builds on data from a questionnaire study, answered by 1,414 students in grade 9 (age 15–16) in Sweden, prior to their choice of upper secondary school. In addition, data from earlier studies, have been included. Results show that the majority plan to transit to further levels of education. There is, however, a group of students who opt to move directly into work. In relation to making an educational choice, the factors that dominate the decision-making processes of students are related to; interest and ability, wellbeing and fun, but also plans after upper secondary school. Views and choices among friends and adults outside the family, is of less importance. With regard to perceptions of a future life, what dominates students’ thinking relates to their views of a secure and comfortable life. Comparisons between boys and girls and between students with parents born outside Sweden and students with native-born parents, show similarities as well as differences. Drawing on our results, we argue that career learning needs to be flexible and adapted to the students’ different situations and needs.