The opening chapter of The Writing Life focuses on general advice Dillard has for the aspiring writer. She addresses the writer directly, urging them to use a line of words like a laborer uses a tool. The writing process is like the demolition of a house, wherein the writer will have to get rid of the earliest foundational passages if there are structural faults. Dillard explains the necessity of revision with anecdotes about a novice photographer and a songwriting cab driver. Both artists were so attached to the difficulty of their artistic process that they didn’t have the courage to throw out poor-quality pieces. Dillard returns her earlier construction metaphor with another anecdote: A building crumbles because workers refuse to acknowledge the cracks in the foundation, despite warnings from someone with an outside perspective. Dillard advises writers to seek out any fractures in the foundation of their own work and to not be afraid if they must start over from scratch.

Dillard delves into the concept of following a work wherever it leads through several anecdotes about courage and fear. She observes a timid but stubborn inchworm moving blindly from grass blade to grass blade, and she recalls stories of a rabbi and butcher both praying for mercy before beginning their work.