When Neil Swanson attempts to train Tom as a plowboy, he shows little interest and makes several mistakes. Swanson punishes him by assigning him unappealing duties such as cleaning the barn and milking the cows. During one incident, the cows gain access to a nearby cornfield where they gorge themselves on their fill of corn. When Swanson discovers the sick cows, he punishes Tom by forcing him to herd wild horses. Tom finds this work surprisingly likeable and begins to attempt the taming and riding of some of the unbroken horses. However, when Benny spots him in this act, he removes him from the job and sends him back to the cow barn. When spring arrives, Tom begins to work as a shepherd with Albert Left Hand.
Albert Left Hand rarely interacts with Tom, and when he does talk, he criticizes Tom for his laziness and expresses his bitterness about life. Nonetheless, Tom finds a certain degree of solace in his work, as it allows him to experience the outdoors. After learning to help the ewes give birth, Tom succeeds in saving the majority of the newly born lamb that season. He travels to Bayfield to sell the wool he has shorn from the sheep.
During his trip to Bayfield in order to sell the wool, Tom recognizes a bridle in a storefront as the exact bridle he made in school and is shocked at the high price tag on the item. Two cowhands in Bayfield challenge Tom to ride a wild horse, promising to award him a quarter should he succeed. While Tom stays on the horse, Slim, his challenger, falls off. Slim ups the ante by offering Tom a dollar if he can repeat such a performance. After two successful rides, Red Dillon, who makes his living by breaking broncos, approaches Tom, offering him a job in New Mexico. There he owns a herd of wild horses, and he promises to educate the boy in all aspects of bronco taming and riding. Eager to take the job, Tom explains that he must first talk to his current employer, Albert Left Hand.
In this phase of Tom's life he has little control over the events of his life. During his life in the wilderness, Tom had been largely able to determine his own fate and to make his own decisions. His well being had been inextricably linked to the natural world, but he had controlled all the other elements of his existence. In his life in Pagosa, on the other hand, his fate rests in the hands of authority figures such as schoolteachers and bosses. They constantly shuffle him from one occupation to another, with little regard for his feelings on the matter.
Tom's attitudes toward his job as a plowboy in many ways reflect his Native American heritage. The smells on the farm, unfamiliar to Tom, constantly nauseate him. He also finds plowing a futile practice. Borland writes, "But plowing seemed stupid to him. Why should anyone rip up the grass, even if it was sparse grass, and make the earth grow something else? If left to itself, the earth would grow grass and many other good things. When you plowed up the grass you were making the earth into something it did not want to be." This passage expresses beliefs consistent not only with Tom's individual beliefs but also with Native American beliefs in general. Native Americans often found European methods of farming, which involve a significant reworking of the land, contrary to the natural order of the world. In accordance, Tom questions the practice of plowing as it attempts to force the land to produce certain plants.
When Benny catches Tom attempting to ride the unbroken broncos, Tom contemplates the domestication of horses and its novelty. Borland writes, "In the old days people had respected their horses, tamed them. But the old days were gone. Now they broke their horses, broke their spirit." To a certain extent, his thoughts about unbroken horses serve as a metaphor for his own situation. Tom, like a wild horse, had possessed an inherent sense of rebellion. While this rebelliousness often complicated interactions with authorities and manifested itself violently or explosively, it also represented an important part of Tom's personality and spirit. However, when the painful events of his life became too much of a burden to bear, Tom crumbled under the pressure and consequently lost the passion that had accompanied the wildness. His efforts to come to terms with the civilized world eventually "broke his spirit" as well.
In Chapter 21, the author speaks to the economic exploitation of Native Americans during the time period in which this novel is set. When Tom spots the bridle he has produced, free of charge, for sale in a shop window for a price of five precious dollars, this exploitation becomes clear. Such practices occurred with some regularity in this era.