After a failed business venture with his brothers, Irving filed for bankruptcy in 1818. Despondent, he turned to writing for possible financial support, although he had difficulty thinking of stories to write. He stayed in Birmingham, England, where his brother-in-law Henry Van Wart had opened a trading firm. The two were reminiscing in June 1818 when Irving was suddenly inspired by their nostalgic conversation. Irving locked himself in his room and wrote non-stop all night. As he said, he felt like a man waking from a long sleep. He presented the first draft of "Rip Van Winkle" to the Van Wart family over breakfast.
