This paper discusses advantages and disadvantages of being a researcher in a familiar setting. This study was conducted in a nursery in Turkey. In ethnographic research, conducting research in a familiar setting plays an important role in collecting and analysing data. Familiarisation with participants and settings is associated with 'insiderness' that a researcher shares the same language and culture with participants. The concept of positionality will be used to discuss the researcher's positionalities during the fieldwork. There has been a discussion about the role of familiarisation in conducting ethnographic studies and insider/outsider dichotomy. This study argues that the research process is not unproblematic for an insider researcher. It also indicates that there are advantages (e.g. ethnicity and former teacher) and disadvantages (being a male researcher) of being an insider in a familiar setting. The study highlights that the researcher made the arrangements to overcome challenges resulted from the researcher's gender.