In 1902 Lewis went to Oberlin Academy. While there, he developed a religious enthusiasm that fluctuated during the majority of his teen years. In 1903 he attended Yale and worked towards his bachelor's degree. Prior to receiving it, however, he took some time off to work at the socialist commune, Helicon Home Colony, and to travel to Panama. Because Lewis was ugly and seemed self-absorbed to a lot of people, for the most part he had a hard time making friends at both Oberlin and Yale. There were a few exceptions, however. He was able to maintain a handful of relationships with some professors and students who saw promise in his writing.
After earning his bachelor's degree in 1908, Lewis wrote for newspapers and publishing houses in hopes of becoming a full-time writer. That same year he moved to New York City where he became a freelance writer. In 1912, Lewis published his first novel, Hike and the Aeroplane. In 1914, he married Grace Livingston Hegger, and also published Our Mr Wrenn: The Romantic Adventures of a Gentle Man. Subsequently, he published The Trail of the Hawk in 1915. Two years later, he and Grace had their only child, Wells. In 1920, Lewis published the novel Main Street, his first popular work. This book earned him a reputation as a great novelist. Main Street sold 180,000 copies in the first six months, and within a few years its sales were estimated at two million.
Lewis's most renowned work, Babbitt, was published in 1922. A satire of American culture, society, and behavior, it critiques the vapidity of middle-class American life and its pressure toward conformity.