A better understanding of the experiences of young people before, during and after belonging to an illegal armed group (IAG) can provide information to promote their reintegration into urban settings in Colombia and to help prevent violence. A qualitative study with a hermeneutic historical approach was performed to examine these experiences from the perspective of direct or indirect participants in the armed conflict. Fifty individuals aged 14-24 years (7 women and 43 men) with low socioeconomic status from Medellín were interviewed; 26 of them had a history of direct experience with IAGs. What stands out in their stories are descriptions of obstacles to progress in their lives; lives marked by stigma, poverty, violence and inequality; the differences of opinion among these young people regarding whether to belong to these illegal groups; how becoming an active member of an IAG creates both an opportunity for the present and an additional obstacle for the future, which adds complexity to the risk behaviors they assume; and how the reintegration process offers new expectations regarding access to educational and employment opportunities and social recognition. All of these factors point to the need for not only a comprehensive reintegration process but for more inclusive and equitable social policies, in this case for children and young people.