In this paper, the third methodological approach is reflected by introducing the concurrent research design that aims to combine both qualitative and quantitative and individual and group level data within the same study (Creswell, 2003; Teddlie & Tashakkori, 2009). Moreover the longitudinal approach was selected to identify the significant gaps and consistencies in school path perceived by primary and lower secondary school pupils (n=170). The study aims to gain better understanding about a process in which pupils re-negotiate the fit between themselves and various learning environments provided by school. The school constitutes a multiple, interactive, complementary and sometimes even contradictory learning environments for the pupils. Hence transitions in and between these contexts provide different kinds of resources and challenges for supporting pupils’ well-being and learning. (Pyhältö et al. 2010; Pietarinen et al., 2010.) All the quantitative and qualitative instruments are developed by the authors. The individual level data includes follow-up survey (three measurements) and a written projection task for the same pupils (n=170). The group level data includes group interviews (n=170 pupils) and structured classroom observations during three semesters (ca 1100 lessons). The paper reflects the challenges and potential of combined research methodology in school studies.