When he graduated in 1929, he knew he wanted to attend University of Wisconsin and become a writer, but the coming of the Great Depression put an end to that dream.
With few options available, Motley continued living with his parents and volunteered as an assistant football coach for his high school. Unable to get work, he decided it was time he began to travel and gather material for his writing. In July of 1930, Motley bicycled from Chicago to New York, living the life of a hobo. The next nine years were to become a tangle of travel and writing, winning Motley little monetary reward or recognition. He took several automobile trips to California and the West, living a simple life as he worked as a migrant laborer, cook, photographer, radio scriptwriter, and newspaper editor, among other jobs. It was also during this time that he served a month-long jail sentence in Wyoming for vagrancy. In the midst of his travels, he focused on writing short stories and submitted them to many popular magazines and newspapers. All were rejected. Though he had some success getting travel articles published in the late 1930s, he began losing the support of his family, who felt he was too much of a dreamer.
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