Gentleman Jim is the story of Jim Bloggs, an imaginative toilet cleaner who, dissatisfied with his station in life, devotes his time to envisioning a world beyond it. His walls are lined with books like Out in the Silver West, The Boys' Book of Pirates, and Executive Opportunities, which provide fodder for his ruminations on career change. Encouraged by his wife, who is also eager to incorporate more adventure into her life, Jim sets out to bring these dreams to fruition by accumulating various accoutrements, only to discover that the life of an executive, an artist, or a cowboy is more complicated and costly than it appears.