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Several contemporary theories of offending over the life course assume an unequivocal distinction between offending and non-offending and, in parallel, between offenders and non-offenders. This dichotomized stance is rooted in the idea that “crime is bad” and is fostered by a wish to prevent the occurrence of this type of behaviour. In this presentation, it will be argued that while this is a commendable goal, a thorough understanding of the phenomena of offending over the life course requires that we extirpate our thinking from this value-ridden premise. Specifically, it will be argued that offenders are purpose-driven beings-in-the-world who must compose with various contexts of action over their life courses and who can mobilize offending as a means of power to reach a fundamentally human desire: a felt sense of self-worth. Drawing on data from a large sample of individuals incarcerated in provincial Canadian jails between 2010 and 2013, these ideas will be quantitatively evaluated. The analysis will delve into respondents’ subjective outlooks regarding offending and conventional courses of action, and into their cultural and social repertoires of action to evaluate what makes them more likely to resort to offending. The implications for criminological theory will be discussed.