The basis of this article is a follow-up study of a cohort of pupils in the third largest city of Sweden, Malmö. The pupils finished fourth grade at compulsory school in 2008. We have data about every individual in the cohort as well as corresponding information about their parents. The information concern educational choices, educational accomplishments, employment relations, incomes from work and different kinds of social benefits and allowances. We got annual data on these variables from 2008 until the last follow-up year 2019 when most of the individuals were 21 years old. Most of them left upper secondary school in 2017 when they were 19 years old. They were therefore in the beginning of their transition 2019, either aiming for education or work. The results show that vocational education generated favourable conditions for work and incomes provided that the diploma goals ware reached. Individuals with foreign background and with unfavourable socioeconomic origins were overrepresented among those that didn't reach the diploma goals; this was true for students on VET-programmes as well as higher education preparatory programmes. It should also be mentioned that experiences from a national programme in upper secondary school generally improved conditions for establishment. Those that didn't reach the goals of compulsory school and weren't eligible for studying at a national programme met the greatest difficulties in finding jobs and decent income levels.