This article examines older physical education (PE) teachers’ wellbeing over the course of their career in Finland. The study highlights challenges to physical and mental functioning as well as how teachers respond to these challenges. The six interviewees were over 55-year-old PE teachers, whose career had lasted for more than 30 years. Qualitative methods were used in the collection, transcription and analysis of the research data. The qualitative analysis consisted of a series of interpretations that visualised the world described by the interviewees. All the research participants had physical problems that affected their teaching and make teachers consider a potential career change. To be able to teach, teachers adapted their ways of working according to the challenges brought by age and injuries. The research participants found that the challenges caused by musculoskeletal problems and ageing were an inevitable part of the profession. They emphasised the positive sides of the work: the profession permits varied workdays. In addition, the teachers noted that their work provides them with opportunities to remain physically fit. Teaching health education is a means to lighten the workload of older teachers. PE teachers enjoy their profession and are dedicated to it, despite all the challenges. The interviewed participants clearly experienced work engagement. Our development proposal for teacher education is that future PE teachers be informed about the risks involved in the profession. Such activity helps young teachers reflect proactively on the measures taken to maintain their functioning during their career and on perspectives related to the ways of working.