Vocational teachers in Swedish upper secondary schools are a heterogeneous category of teachers, connected to different types of trade. These teachers represent a broad set of trade skills varying in content and character. In their teacher role, they continue to wear the clothes, speak the language, share the culture and remain mentally in their former professions. Still, it is central that they keep up this contact to be able to school the pupils into the environment of the trade in question, but also to help them to understand what skills a profession demands. However, the individual teacher also has to distance himself from the negative elements in the culture of the profession: patterns and habits that, for various reasons, have to be broken or changed. This paper draws attention to the ways in which a group of vocational teachers, who were participants in a project that aimed to train unauthorized vocational teachers, expressed their ambitions to prepare the pupils for a future professional career. When collecting information, we used the degree dissertations they produced and discussed in seminars, and informal dialogues. The result shows that it is important that the instruction location resembles a real working site as far as possible. These places are more or less realistic copies of a garage, a restaurant kitchen, a hairdressing salon, and so on, in order to give the pupils a realistic setting for instruction. However, the fact that these simulated workplaces lack the necessary support functions that exist in a company creates problems, problems which make a lot of extra work for the teachers. Vocational teachers also have to instruct the pupil in the experienced practitioner’s professional skills and working situation, but the pupil herself/himself must learn the job by doing it in practice. Some vocational upper secondary programs lack relevant course literature and the businesses give little support. This also makes extra work for the teachers. Moreover, the distance between the vocational programs and the trainee jobs was experienced as being difficult to overcome. One reason seems to be differences between businesses and differing preconditions between small and big companies’ abilities to take care of these pupils. The upper secondary school vocational programs also play a role in cementing existing gender roles, as well as perpetuating class-related patterns on the labour market.