This essay, adapted from a speech upon receipt of the 2018 Richard P. Kern Memorial Award from the National Association of Sentencing Commissions, details why sentencing is “dang hard” and explores implications of that reality. The essay argues that the challenges of sentencing not only demand that all jurisdictions have a sentencing commission as an essential permanent agency, but also call for these commissions always to think big and to strive to work deep and wide to study all facets of modern criminal justice systems. The essay also contends that sentencing errors may be quite common and that, even if we manage to get sentencing “right” at the outset, changes in society and in individuals can make even “right” sentences wrong over time. Sensible humility about the likelihood of sentencing errors further suggests, for example: at the rule-making stage, having sentencing laws include sunset provisions and having sentencing commissions review and audit major guidelines and related sentencing practices on a regular basis; at the case-specific stage, having far more robust substantive appellate review of sentences, having more robust mechanisms for parole and judicial reconsideration and clemency, and even developing more creative means to apply and revise different forms of punishment as time passes and new information is gathered.

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