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Also contributing articles to a local newspaper in Pensacola, Florida called the The Playground News but was forced to write anonymously due to Air Force regulations of no outside employment. "In summary, this airman, although talented will not be guided by policy, Sometimes his rebel and superior attitude seems to rub off on other airmen staff members," wrote Col. William S. Evans to describe Hunter's release from the Air Force. Hunter left the Air Force in 1958 under the title Airman First Class and received an honorable discharge despite his attitude towards his superior officers.

After his stint in the Air Force, Hunter eventually began his long road in his career as a journalist in 1958 by accepting the position as a sports editor in Jersey Shore, Pennsylvania. After moving to New York City Hunter began to attend classes at the Columbia University school of General Studies but only part-time where he spent most of his time at Time working as a copy boy for fifty-one dollars a week. During this time, Hunter would spend countless hours copying The Great Gatsby using a typewriter in order to "learn the styles of different authors. He was fired from his job as a copy boy in 1959 and eventually landed a position as a reporter for the Middletown Daily Record in Middletown, New York where he was fired after destroying a candy machine and arguing with advertisers of the newspaper.

Hunter eventually found work with a newspaper called the Sportive. This is where Hunter moved to San Juan, Puerto Rico in 1960 where he would eventually get the inspiration to write his first book The Rum Diaries. After the newspaper, folded Hunter became sick of the hot weather and the sub-par conditions, he moved back to the continental United States. He worked as a caretaker and a security guard at the Big Sur Hot Springs in California eventually finding enough time to begin to write his first two novels, The Rum Diary and Prince Jellyfish. He was later fired from his job stemming from his article regarding the bohemian culture of Big Sur at the time in 1961.

Searching for more work, Thompson became a reporter for the newspaper The National Observer that allowed him to travel throughout South America mainly in Brazil. This is where he met his first wife Sandra Dawn Coklin, they were eventually married in 1963 when she eventually joined him in Rio. They eventually moved to Aspen, Colorado where Hunter and Sandra conceived their first son Juan Thompson. Sandra and Hunter would eventually

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