Sentencing involves the deliberate infliction of harm by society on individuals. It is the most coercive means through which the community imposes its collective (albeit civilised) displeasure at harmful conduct. It is an important and complex process, which involves balancing fundamental interests of victims and the community on the one hand and offenders on the other. The single most important determinant in setting criminal sanctions is the principle of proportionality, which provides that the harshness of the penalty should match the seriousness of the offence. The principle is intuitively appealing but in reality is an illusion, and hence the reason why penalties for criminal offences vary enormously within and across jurisdictions. The main reason is because there is no agreement regarding the considerations that inform offence severity or sanction hardship. This article injects content into the proportionality principle by suggesting that both limbs of the principle should be informed by the extent to which the crime and the sanction set back the well-being of victims and offenders, respectively. These interests are not conclusively mapped. However, a methodology is set out for establishing these interests. This will lead to greater consistency in sentencing and provide a sounder, normative foundation for the manner in which society deals with criminals.