Estonian students achieved high scores in the latest Programme for International Student Assessment surveys. At the same time, there needs to be more knowledge about the teachers guiding these students, as this could provide insights into effective teaching methods that can be replicated in other educational contexts. According to the Teaching and Learning International Survey, Estonian teachers' average age is among the highest in the world, and the shortage of young, qualified mathematics teachers is well-documented. The present study aimed to map the motivating and demotivating factors for mathematics teachers to continue working in this profession. The effective sample comprised 164 Estonian mathematics teachers who responded to items regarding self-efficacy and job satisfaction and open-ended questions about motivating and demotivating factors regarding their work. The results showed that "students," "salary and vacation," and "job environment" are both motivating and demotivating for mathematics teachers. On the one hand, helping the students to succeed (and witnessing the progress), satisfying salaries and a good job climate motivate the teachers. And at the same time, students' low motivation, poor salary, and straining work conditions (e.g., very high workload) serve as demotivating factors. We showed that mathematics teachers' work experience is an essential factor to be considered when thinking about motivating and demotivating factors for teachers, as well as their self-efficacy and job satisfaction. The reasons, possible impact, and potential interventions on an educational policy level are discussed.