Drawing on Pierre Bourdieu’s theory of practice, this study explored the construction of technological expertise of eight teenagers (five boys and three girls) aged 13 – 17. The qualitative study specifically employed observations and interviews and focused on home computer use, which for many of the participants was their primary site of leisure. All of the participants considered themselves to be technological experts, and their peers and/or their family supported this premise. This paper outlines findings that identify the participants’ multiple (and contradictory) understandings of expertise and the ways the participants perceive they have attained expertise and perform as experts in out-of-school settings. Traditional views of expertise are contrasted with what the teenagers think about their development of expertise, predominantly using Bourdieu’s framework for analysis. As almost all of the experts in this study gained their expertise through independent means, with minimal input from their schooling, discussion focuses on the trajectories to expertise inherent within these sites of informal learning, and what this might mean for pedagogy and formal learning.