This article addresses the change in the transitional process from secondary school general education to gainful employment within the framework of societal modernisation processes in Germany. We analyse the relationship between the options for and restrictions upon individual educational mobility under the conditions imposed by the various socially institutionalised educational segments, which comprise a structure of opportunity. The database for our study consists in the longitudinal findings of the "Hamburg Biography and Life Course Panel" (HBLP) from 1980 to 2007, which examined the processes of vocational education mobility for a sample of the Hamburg graduating class of 1979. How do these people manage their educational strategies? What do they experience in terms of vocational education and continuing education within the institutional structure of opportunity? Do the career paths differ after gender?