More True Confessions of a Legal Writing Professor: When You Get Stuck in Legal Writing, Channel Your Inner Jackson Pollock (and Other Strategies) 

Abstract

Even seasoned legal writers experience moments of paralysis—those dreaded brain freezes where anxiety and self-doubt override the technical skills we’ve honed. In this humorous yet practical essay, legal writing professor Diana J. Simon offers an honest confession: writing is hard, and perfectionism can sabotage progress. Drawing on personal experience, and cognitive strategies, Simon shares a toolbox of techniques to help legal writers get unstuck. From channeling Jackson Pollock in a splatter-draft to managing competing inner voices through Betty Sue Flowers’s “Madman, Architect, Carpenter, Judge” framework, the piece offers concrete, compassionate advice. Additional tips include reverse outlining, targeted revision tasks, and jumping into the middle of a draft. Throughout, Simon reminds us that great writing is not about perfection on the first try—it’s about the persistence of rewriting. Her message to lawyers and students alike: embrace the mess, fight the fear, and write your way through it.

Keywords: legal writing, rewriting, targeted revision tasks, reverse outlining