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AbstractThis article explores the anthropological notion and methodology of serendipity as applied to youth work and non-formal education training methods. I introduce the term and its uses by drawing connections to the concept of ethnographic fieldwork and strategy to approach anthropological contexts. I then draw a parallel between the role of the anthropologist and the youth worker. I investigate the different options when dealing with groups and facing the contradictions of conducting fieldwork or trainings. Thus, I propose a distinction between the anthropological concept of ‘serendipity’ and the youth work-related concept of ‘improvisation’. I present ambiguous cases of the serendipity process and their implications based on my own direct experience of involvement with youth work through the methodology of autoethnography. Finally, I address different perspectives of serendipity seen as a storytelling construction. Ultimately, I draw useful conclusions on the understanding of serendipity and improvisation in the two contexts.