Two years ago, when I was asked to conduct a study on young NEETs (acronym for Not in Education, Employment, or Training) who experience social distress, I soon thought of applying a qualitative methodology, as I realized that I was confronted with an insight into a very complex social reality. Research on NEETs often reports on this widespread phenomenon and how young NEETs run the risk of finding themselves in social distress. However, this phenomenon is rarely studied in depth trying to understand, through an interpretative approach, the way in which young people structure their daily lives and develop strategies to find a way out of their distress. Studying this social reality through shadowing allowed me to observe the individual in his or her own context, and to understand the everyday logics and social practices in which he or she is involved. Entering the “folds” of everyday life was entering a place where situations are taken for granted, are familiar and obvious. It is in everyday life that every individual attaches sense and meaning to the interactions and the social reality in which he or she is embedded. This experience has taught me that shadowing is a particularly appropriate technique to understand how the participant acts in contexts of social everyday life and which strategies he or she enacts to cope with difficulty. In this case, I present an example of shadowing, explain how it is conducted, and how data are collected and analyzed.