This article explores the process through which John Steinbeck wrote "The Grapes of Wrath." This process can be viewed as a learning process with elements of self-directed and transformative learning. Using primary and secondary sources, including a journal Steinbeck kept while writing the book, four themes are discussed: (1) Steinbeck's learning was a process that, unlike the actual writing, did not take place in isolation; (2) the juxtaposition of Steinbeck's confidence and productivity with examples of struggle and self-doubt; (3) a comparison of individual and social dimensions of self-directed learning; and (4) in writing the book, Steinbeck underwent a major transformation that had both negative and positive ramifications. This study continues a line of scholarship on self-directed learning using biographical case study to understand self-direction in the lives of others.