Researchers conducting fieldwork, especially in comparative social research, face the complex issue of conceptualizing and practicing positionality. How we position ourselves affects the research approach, the interpretation of the data and, therefore, the whole research process. This paper discusses my own in-between or ‘in-out-sider’ positionality during my fieldwork studying the experience of youths in social movements in Thailand and Myanmar in 2020 and 2021. Drawing on data from a visit to Thailand and interviews with 40 Myanmar and Thai youths who participated in the movements, this article documents my experience of the subtle nuances of multiple positionalities and how I navigated through the fieldwork as an in-out-sider researcher. In this comparative context, especially, I believe that my in-out-sider positionality facilitated the research process, from interviewing participants to conducting the field visit. The discussion of this contextually situated positionality challenges the typical explanations of the insider/outsider dichotomy, suggesting the need for a rethinking of certain aspects of this explanation, such as the background and experience of the researcher, and the context in which the researcher and the researched interact. This paper therefore contributes to knowledge around this subject and its application, particularly in the context of comparative social research which studies specific groups of youth activists or protestors.