In participants’ accounts, initial and continued involvement in offending was linked to developing friendships with people involved in crime, the onset of personal problems, and the onset of financial problems. Desistance from offending was linked to personal development, experience and fear of getting caught, changes in rational evaluations of crime, shifts away from friendships with people involved in crime, the presence of more positive social relationships in participants’ lives, and the removal of financial problems. Gender emerged as an important overarching concept that colored the ways in which other concepts played out in the participants’ accounts of themselves and their involvement in crime. Participants’ descriptions of desistance indicated that this came about through changed evaluations of offending together with changed relations to society. Changes in identity appear to be an essential element in the processes for desistance. Developing a theoretical understanding of the processes that influence criminal behavior has been a complex and continuously-evolving task. Theories of crime are many and diverse. Findings are presented from a study which explores theoretical explanations of crime in the light of insights from offenders’ descriptions of their own involvement in crime and considers how insiders’ perspectives relate to academic understandings of offending. The study consisted of 18 convicted offenders, 9 men and 9 women. Figures, references