Teachers are one of the main factors that determine the quality of education. Their way of teaching and perceiving can influence student development in many ways. In this regard, it is important to explore the experiences of teachers and the various factors that have influenced the shape of their experiences. According to The Teaching and Learning International Survey (TALIS, 2013), Korean teachers have reported less job satisfaction than that of Norwegian teachers (OECD, 2014). To compare the educational reality between Korea and Norway, this study focuses on the experiences of Social Studies teachers (SSTs), and divides them into five main areas: perception of the subject, class practices, interactions with students, interactions with colleagues, and working environments. This study adopts a qualitative strategy and comparative case design. Data was mainly collected through semi-structured interviews with five Korean SSTs and four Norwegian SSTs. Participant observations and document studies were also conducted in order to gain more contextual understanding. The data analysis was guided by thematic analysis and through the lens of ‘reflective practice’ as well as Bronfenbrenner’s ecological system theory. It has been found that both groups of SSTs in the two different countries often regard the goal of Social Studies as fostering independent thinking with critical attitudes in their students. They also recognize that Social Studies deals with a variety of changes in society, and consequently prefer to conduct an activity-oriented class based on horizontal relationships with their own students. The differences between the two groups mainly derive from their respective social context, in which educational policies as well as socio-cultural aspects have significantly influenced the shape of their experiences in teaching. Especially, the two different grading systems, the Relative in Korea and the Absolute in Norway, play a big part in the differences because it impacts the teachers’ class practices and interactions. For the Korean teachers in this study, it has been especially difficult for them to harmonize the activity-oriented class with the required assessment. Compared to the Norwegian teachers, the Korean teachers have a less communicative culture and more intensive workloads. In this regard, it can be said that Korean teachers experience more pressure in their careers than that of their Norwegian counterparts.