Dickey taught as an instructor of English at Rice University (then Rice Institute) in Houston, Texas in 1950 and, following his second Air Force stint, from 1952 to 1954. After teaching at the University of Florida during the 1955–1956 academic year, he worked for several years in advertising, most notably writing copy and helping direct creative work on the Coca-Cola and Lay's potato chips campaign. He once said he embarked on his advertising career in order to "make some bucks." Dickey also said "I was selling my soul to the devil all day... and trying to buy it back at night." He was ultimately fired for shirking his work responsibilities.