
After leaving the military, Thompson began Columbia University's School of General Studies. Studying under the GI Bill, he also worked as a sports editor for a newspaper company. Thompson also began to focus more on literature
instead of being as reckless as he was during his earlier years. He also worked for Time Magazine as a copy boy. While working for Time he made copies of Ernest Hemingway's A farewell to Arms and F. Scott Fitzgerald's The Great Gatsby to observe and learn both of the writer's styles of writing. Later, Thompson was fired by Time for insubordination. During this time period Thompson worked for many different newspaper and printing companies in which he was dismissed from his duties for many different reasons ranging from damaging candy machines to arguing with people.
Thompson could not hold a job so the next best option in his head, was to simply pick up and move. Thompson moved to Puerto Rico, where he also could not hold a job. However, his time spent there was later discussed in two novels one including The Rum Diary. Thompson viewed himself here as an observer of what went on around him. Carr describes Thompson as "the observer not only changes events by his presence, but his presence also frequently surpasses the event in terms of importance. (Carr). After moving back to the states, he began working longer for different companies, holding jobs for more than a few months. Also, he began illustrating his own articles for National Observer and Brazil Herald.
In May of 1963, Thompson married his girlfriend Sandra Dawn Conklin. She had accompanied him to countries previous to their engagement and wrote articles with him. Now married, Thompson and Conklin moved to Aspen, Colorado where they started a family. Juan Fitzgerald Thompson was born March 23, 1964. The family moved to California in 1964 where Thompson continued to write for the National Observer where he introduced himself to the hippie culture and lifestyle.
Carr, David. "The Thompson Style: A sense of Self, and Outrage." The New York Times 22 Feb.2005.Web.