Abstract: This article presents findings from a research project that set out to inform our understanding of crime by exploring offenders' accounts of themselves, their lives and their offending behaviour. Eighteen convicted offenders were interviewed. Official data about their offending were also collected. Analysis of these qualitative data revealed two central concepts in participants' accounts of their involvement in crime that are reported here: (i) crime orientation – an individual's stance towards crime; and (ii) social relations – an individual's formal and informal connections to society. More positive crime orientations and more negative social relations were associated with deeper levels of involvement in offending. The analysis also indicated that these were gendered concepts, being experienced differently and having different implications for men and women. It is concluded that crime orientations, social relations and gender are central to understanding offending behaviour when seen from offenders' perspectives.