[6] As an undergraduate student at Amherst College, Conover was fascinated by books he had read about American railroad hoboes and he decided to make their lifestyle and experiences the topic of his senior thesis.
[3] The notebooks Conover kept during these four months became the raw material for his senior thesis, "Between Freedom and Poverty: Railroad Tramps of the American West," upon which Rolling Nowhere is based.
[3][2][6] Rolling Nowhere documents Conover’s time as a well-educated, middle class man in his early twenties covertly traveling the rails and living with several different railroad hoboes across more than ten states in the American Midwest and West.
[3] The book provides many anecdotes that illustrate the vulnerability of railroad hoboes to intragroup violence and racism, to harassment and suspicion from outsiders, to health and hygiene challenges, and to economic precariousness.
[3] Many of the hoboes Conover encounters are military veterans or men who have struggled to meet American society’s expectations for successful male breadwinners.