Learning difficulties have been found to dilute the possibilities that young adults have in their educational careers. However, during the last few decades, education has become increasingly important for employment and overall life satisfaction. In the present study, we were interested in the effects of mathematical and reading difficulties and socioemotional and behavioural problems (measured at age 16) on three educational situations at age 21: delayed graduation from upper secondary education, short educational trajectory and not being engaged in education, employment or training (NEET). The participants (N = 597; 304 females, 293 males) were one age cohort of ninth graders in general education classes, who were followed for five years after completion of compulsory education. This time frame included two different transition phases: first, from comprehensive education to upper secondary education, and second, from upper secondary education to further studies or to working life. Structural equation modelling was used as analysis method. The findings show that mathematical and reading difficulties as well as socioemotional and behavioural problems had significant long-term effects on the participants' educational careers. New in part was that these learning difficulties seemed to have somewhat divergent emphases on the three investigated life situations: (1) mathematical difficulties, more strongly than reading difficulties, caused the students to attain lower levels of education, (2) mathematical difficulties and socioemotional problems predicted a student ending up in the NEET group and (3) reading difficulties and behavioural problems predicted delayed graduation from upper secondary education.