This essay focuses on an aligned perspective between criminologist and practitioner. It identifies a shared experience. So many factors critical to helping someone on the path to rehabilitation are common, regardless of offence. A body of research and practice exists that clearly associates childhood deprivation, poverty (physical, mental and emotional) and negative lifestyle factors (poor educational achievement, delinquent peers) to criminality (Cohen, Smailes and Brown, 2004). Together, we explore both Kieran’s academic perspective and Lisa’s evidence-based practical response – borne out of over ten years working with young people for whom incarceration seemed a risk, though not inevitable – to the question posed by this book.