Context: The standing of VET depends on a multitude of factors and differs significantly between countries and regions. This also impacts access to VET and whether students see VET as an option to continue their education and training or to start their careers. Students typically transition into VET either after the lower secondary or the upper secondary level. It is a transition from school to VET, and from an individual perspective, it is a transformation. There is a sound body of scientific work looking at the transition from school to work from different perspectives (e.g., policy, economy, and sociological perspectives). An often-neglected focus is on the challenges students face, the transformations they undergo in the transition, and the support they receive from parents and teachers in this situation. Approach: We use data from two studies, a cross-sectional study with students heading towards a specialized school on the upper secondary level, www.infosetting-bl.ch. And a longitudinal study at www.digibe.ch, where we follow students at the lower secondary level over three years. The study started in autumn 2022, so the students are now in autumn 2023 at the beginning of their third year, The project focuses on reflection and transformation in and through career planning. In this paper, we report the first results on how parents and teachers were involved when irritating situations occurred in career planning. Findings: We find that the role of teachers and parents is multifaceted, including guidance, support, and counselling. Both studies show, however, that teachers and parent rarely focus on future-oriented interventions; at least from the perspective of the students. Conclusion: Career education is a concept that fits better to frame the work a teacher does in supporting their students in career planning. Two aims in career education are of high relevance: fighting the stereotypes many students have about iVET and VET and their ability to cope with irritating situations in career planning and career choice processes.