This article is, if you will, an extension of the book 21 Voces, Historias de Vida sobre 40 años de Educación en Colombia by professors José Darío Herrera and Hernando Bayona Rodríguez, not because it includes new voices to the story, but because it seeks to analyze, identify and establish positions, affinities, tensions and challenges that arise from the experiences narrated by 21 influential educators in the field of Colombian education. In this way, as in the text mentioned above, it does not attempt to make a chronological reconstruction of the events that occurred from the end of the 1960s to the present day. Rather, it seeks to identify the conditions under which these life stories were born, that is, the struggles, motivations, encounters and disagreements with institutions, teachers, unions, research groups, social movements, cultures, and, above all, with the children and adolescents in Colombian schools. These relationships allowed, in most cases, the emergence of projects that impacted the country’s education.