When he graduated in 1974, having just turned twenty-one, Hiaasen was hired by Cocoa Today as a general assignment reporter, and soon after became a feature writer for their Sunday magazine, Sunrise. Two years later, in 1976, he was invited to join the Herald's Broward Bureau, where he remained for about six months before being moved to the newspaper's city desk in Miami as a general assignment reporter. He quickly became a feature writer for the Herald's Sunday magazine, Tropic, and in 1979 joined two-time Pulitzer prize winner Gene Miller, associate editor for reporting, in investigating and writing "Dangerous Doctors," an eight-part series remembered today for its excellence and impact.

During the early 1980s, while still a member of the investigations team, Hiaasen began to write fiction, spending evenings and weekends co-authoring, with the late William Montalbano, three novels—the recently reprinted Powder Burn, Trap Line, and A Death in China. In 1985—as he was about halfway through his first solo novel, Tourist Season, one of seven (Double Whammy, Skin Tight, Native Tongue, Strip Tease, Stormy Weather, and Lucky You) that established his national reputation as one of America's best satirists—the Herald asked Hiaasen if he wanted to write a column.

Those at the Herald who knew him during these early years say that even in his twenties Hiaasen was clearly one of a kind, his gifts being distinctly extraordinary. Doug Clifton remembers Hiaasen as "a young man with talents that far surpassed those that you would expect from someone of that age and experience." Immediately evident, Clifton says, were Hiaasen's wit, probing mind, remarkable energy and the "incredible ability to handle himself in tough situations, to write with clarity, and to peer into things and catch their essence."