Lawson's first published poem was 'A Song of the Republic' which appeared in
The Bulletin, 1 October 1887; his mother's radical friends were an influence. This was followed by 'The Wreck of the Derry Castle' and then 'Golden Gully.' Prefixed to the former poem was an editorial note:
Lawson was actually 20 years old, not 17, but the editor showed good judgment in recognizing the poet's ability so early.
In 1890-1891 Lawson worked in Albany. He then received an offer to write for the Brisbane
Boomerang in 1891, but he lasted only around 7—8 months as the
Boomerang was soon in trouble. He returned to Sydney and continued to write for the
Bulletin which, in 1892, paid for an inland trip where he experienced the harsh realities of drought-affected New South Wales. This resulted in his contributions to the Bulletin Debate and became a source for many of his stories in subsequent years. Elder writes of the trek Lawson took between Hungerford and Bourke as "the most important trek in Australian literary history" and says that "it confirmed all his prejudices about the Australian bush. Lawson had no romantic illusions about a 'rural idyll'." As Elder continues, his grim view of the outback was far removed from "the romantic idyll of brave horsemen and beautiful scenery depicted in the poetry of 'The Banjo' Paterson".
Lawson's most successful prose collection is
While the Billy Boils, published in 1896. In it he "continued his assault on Paterson and the romantics, and in the process, virtually reinvented Australian realism". Elder writes that "he used short, sharp sentences, with language as raw as Ernest Hemingway or Raymond Carver. With sparse adjectives and honed-to-the-bone description, Lawson created a style and defined Australians: dryly laconic, passionately egalitarian and deeply humane." Most of his work focuses on the Australian bush, such as the desolate "Past Carin'", and is considered by some to be among the first accurate descriptions of Australian life as it was at the time. "The Drover's Wife" with its "heart-breaking depiction of bleakness and loneliness" is regarded as one of his finest short stories. It is regularly studied in schools and has often been adapted for film and theatre.
Lawson was a firm believer in the merits of the sketch story, commonly known simply as 'the sketch,' claiming that
"the sketch story is best of all." Lawson's Jack Mitchell story,
On The Edge Of A Plain, is often cited as one of the most accomplished examples of the sketch.
Like the majority of Australians, Lawson lived in a city, but had had plenty of experience in outback life, in fact, many of his stories reflected his experiences in real life. In Sydney in 1898 he was a prominent member of the Dawn and Dusk Club, a bohemian club of writer friends who met for drinks and conversation.