This paper addresses how emotionally challenging experiences during work-basededucation may influence the professional becoming of student teachers and medicalstudents. We conducted a qualitative analysis of eight focus group interviewswith undergraduates from two universities in Sweden who studied to become eitherphysicians or teachers, and interpreted their experiences through Wenger’s theory ofcommunities of practice. The findings show that students’ ideal view of how to becaring in their aspiring professional role as physician or teacher collided with existingpractices, which affected them emotionally. In particular, the students found itchallenging when norms and practices differed from their values of professionalismand when the professional culture within practices reflected hardness (physicians) orresignation (teachers). Both medical students and student teachers experienced thatprofessional decision making and legitimacy challenged them emotionally, howeverin different ways and for different reasons. This study makes visible both generaland specific aspects of how students view their future role in the welfare sector andchallenging dimensions of professional practice. The findings bring into focus thequestion of how professional education can support students’ professional becomingin relation to their emotional challenges.