This paper investigates the transitions to secondary and to tertiary education. As a new contribution to prior scholarship, it focuses on the role of self-perceived ability (self-assessment), which might impel pupils to make costly efforts in education now, in order to have an uncertain payoff later on. The paper builds on the assumption that while making educational decisions, especially low-educated families overemphasise ability relative to effort. Therefore, there is a need to identify the factors that contribute investing effort in education. It will be revealed that self-assessment might be such a factor in educational transitions. It especially helps the offspring of low-educated parents to reach their potential and to opt for college-bound secondary tracks. The paper concludes that it would be useful to concentrate more on how "effort" is influenced by parental background, since our knowledge is still limited about this kind of influence.