When Sandburg was nineteen, an economic depression that had begun a few years earlier had settled across America. Thousands of hobos took to riding the rails looking for work and young Charles Sandburg gladly became one of them. He headed west out of Illinois into Iowa, still further west out into Nebraska, then down into Colorado and then east into Kansas and Missouri. Carl worked as an apple picker, a waiter, a cook, as a laborer on a railroad section gang and on a wheat threshing crew. Carl also learned from his fellow hobos the songs and ballads they sang at night in the camps.
This was the beginning of Carl Sandburg's love of American folk songs that he continued to collect and sing throughout his life. Carl Sandburg eventually worked his way back to Galesburg four and one half months after leaving but he never forgot his hobo days, the common and sometimes desperate men he met on the way, and he never again felt completely rooted to one place. He wrote in Always the Young Strangers:
"I was meeting fellow travelers and fellow Americans. What they were doing in my heart and mind, my personality, I couldn't say then nor later and be certain. I was getting a deeper self-respect than I had had in Galesburg, so much I knew. I was getting to be a better storyteller. You can be loose and easy when from day to day you meet strangers you will know only for an hour or day or two...I was working out of my bashfulness."