On his court date, the judge told him to pay a ten-dollar fine or spend ten days in jail. Sandburg chose jail (Hacker 45-46). Sandburg recalled his dark moment of that unfaithful night in a poem called "Boes":.
"I waited today for a freight train to pass.
Cattle cars with steers butting their horns.
Against the bars, went by,.
And half a dozen hoboes stood on.
Bumpers between cars.
Well, the cattle are respectable, I thought." (Hacker 46).
After his hobo adventures, Sandburg paid his service in the Army during the Spanish-American War. Following the War, Sandburg received a free tuition to Lombard College (now Knox College) in Galesburg where he wrote his first poetry (Byers 461). After a year of college, Sandburg dropped out saying nothing more than, "I felt the call elsewhere" (Hacker 44). Sandburg then had and opportunity to attend the U.S. Military Academy at West Point, but he did not get accepted because he had failed the mathematics and grammar part of the test (Hacker 41). For three and a half months of his nineteenth year, he traveled throughout the West developing a sense of loyalty to his country and the people and listening to their stories, which transformed his poetry (Niven). In 1904, Sandburg returned to Galesburg where he got a few of his works published (Crowder 36). Soon after returning back to Galesburg, he began to feel bored. So with a suitcase in one hand and a guitar in the other, Sandburg once again left Galesburg in 1905, never to call it home again (Hacker 48). On returning back to Chicago, he was hired as associate editor of The Lyceumite (Hacker 51). December of 1907, Sandburg met his future wife, Lillian Steichen. She was a schoolteacher that shared the same passions for literature (Hacker 52). Sandburg took back his Swedish name Carl because Lillian told him "it was more masculine" (Hacker 53). On June 15, 1908, Sandburg married Lillian Steichen and in the next few years had three girls (Hacker 53-56).