How career paths are interpreted and conceptualised by hospitality workers and industry representatives remains underexplored in current literature. In this paper, we highlight and discuss sector-specific and contextual factors that influence the possibility of establishing a career within the Swedish hospitality sector. The paper uses interviews with hotel managers, who describe and discuss motivations and choices made throughout their own careers and interviews with young (former) seasonal hospitality workers who describe and reflect on their future plans and work-life experience. Additional data are derived through observations at national seminars and meetings for representatives from the Swedish tourism and hospitality industry, where issues of competence and careers were discussed. The findings indicate that the shaping of career paths within the hospitality sector is influenced by two normative and discursively produced ‘truths’ about career paths in the hospitality sector: the importance of internal knowledge transfer and the importance of high mobility. These narratives impose expectations on individuals to be mobile, to change jobs frequently and to work their way from the bottom-up within the industry, and are based on a presumption of a diversified and dense local hospitality labour market. However, since the conditions are different due to contextual, geographical features of labour market size and structure, attractiveness of places, etc., these expectations are difficult to fulfil in places other than in larger urban areas. These normative assumptions of what a successful hospitality career is also have consequences for the development of the hospitality sector as external influences of competence from other sectors and higher education are not seen as valuable, which makes the sector self-contained and not open to external, potentially innovative knowledge.