The paper deals with Austrian structures of occupational choice and the development of guid-ance in an international comparison. Addressing the relationship of guidance to socio-economic developments and problems, as well as contradictions involved in individual choice vis-à-vis economic and social demands. Two main challenges arise from that experience: First, the educa-tion and training system requires early choices among many specializations to be taken at age 14/15, resulting in indications for "mismatches" between students' interests and their placement; second, guidance and counselling relies strongly on teachers, and on activities embedded in the normal instruction process. The evidence base is threefold: (1) literature review, (2) policy doc-uments, (3) quantitative data. A main topic is how the freedom of individual choice can be se-cured and supported vis-à-vis economic and social demands in an education/training system that requires early choices of ET-specializations at age 14/15. The question arises, to which extent the given constraints with choice can be alleviated by guidance and counselling. In particular two issues are emphasized, first how the system deals with disadvantaged young people who do not have clear orientations at the early furcation point, and how sex and gender specific differences are are influenced by structure.