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This article proposes an analysis of juvenile penal careers “from the bottom up”, articulating the analytical perspective that Cicourel mobilizes in his pioneering investigation with theoretical borrowing from other sociological perspectives. While research on the experience of young people with youth justice shows that young people’s trajectories often contain complex back and forth movements between legality and illegality, this article reveals more generally that it is crucial to show the determining influence of a social world beyond the juvenile justice institution and to combine the scale of observation in situ with a macro level of analysis both diachronically and synchronously. By documenting two cases, this article highlights the objective and subjective structural resorts involved in young people’s experiences and in turn questions the effects of this experience on the situation of young people. In this way, the article aims to show how much the sociology of Cicourelians – through the care given to the analysis of “background expectations” – allows us to build bridges between theoretical traditions sometimes presented as antagonistic, while at the same time putting researchers working on criminal justice and the experience of its audiences on a very intellectually stimulating track.