This paper focuses on a commonly‐reported horizontal division between what boys feel to be the circumstances surrounding the lives of older generations and those surrounding their own. This aspect of individualization is explored, seeking to discover the discourses today's boys look to for routes to travel in their search for an independent, adult identity. The paper argues that, despite the increasingly fluid nature of the multiple masculinities that each boy, individually, works to create, some of their experiences are surprisingly common regardless of location or socio‐economic background. Following 111 boys aged 11–21 as they attempt to make sense of the messages they hear from home, school, the law and peer culture, I suggest that there has been an apparent narrowing of time and space around boys who see the life experience of figures such as teachers and parents as being too dated to hold relevance for themselves. Likewise the gilded lifestyles of famous sportsmen and stars from the entertainment industry are understood to be alien. This phenomenon forces boys to weigh up the positive and negative examples given by local, ‘older brother’ role models to the exclusion of more traditional figures.