While Woody's early years were spent in relative comfort with his successful businessman father, things changed quickly for the Guthries. After World War I, bad real estate deals led to Charley losing his land, and the kerosene incident left him with a long recovery, according to the Library of Congress. With Nora institutionalized, Charley left for Pampa, Texas, with his two younger children, Mary Jo and George, leaving Woody and his older brother Roy to fend for themselves in Okemah.

The need to survive made 14-year-old Woody Guthrie extremely resourceful. In addition to playing music on the street for change, he picked through the trash to find scrap to sell and stayed with friends or traveled for whatever other work he could find. During his junior year of high school, although he was popular for his humor and music, Woody dropped out to join his father in Pampa. According to the Oklahoma Historical Society, this was where he learned to play the fiddle, banjo, guitar, and violin so he could play at dances for money. But he also worked for a bootlegger, painted signs, and did whatever else he needed to. Despite earning very little money for all his work, as PBS notes, Woody Guthrie was known for giving it away to anyone he thought needed it more than him. This was noble, but it would also cause problems when it came to keeping his young family fed in the coming years.

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