Robert and his younger brother Gilbert worked hard to earn a meagre income from the family farm as their father became increasingly ill. Following William Burnes' death, in 1784, the family moved to the farm at Mossgiel. Robert had received some education as a surveyor and also spent some time as a flax-dresser in Irvine, but with little success. His real passion was poetry. Inspired by the old Scots poets he read and the songs and tales he heard in the Ayrshire countryside, Burns was driven to write. Yet his financial problems continued to trouble him. Early in 1786, Burns decided to emigrate to Jamaica to seek out his fortune. He bitterly scrawled a poem on a guinea note (now in Burns Cottage Museum) recording his decision to leave.

Romantic complications also contributed to Robert's decision to leave Scotland. Already having fathered one child by the family servant, Betty Paton, Robert had met and attested marriage to Jean Armour, the "jewel" of the "Belles of Mauchline". Jean became pregnant with what were to be twins, but her father repudiated Robert as a son-in-law and hounded him in the courts. Robert in turn repudiated Jean and became infatuated with a young highland woman, Mary Campbell, whom he secretly "married" in a gaelic ritual at Stairaird Craig. Robert urged Mary to emigrate to Jamaica with him and sent her to Greenock to await him. He was never to sail for the Indies, however, for events were to happen that would change his life and Scottish cultural history profoundly.

Three events possibly affected Burns' decision to stay in Scotland. In September 1786, Jean gave birth to twins, Robert and Jean, whom Burns delighted in. In October, still waiting for Robert, who by this time had twice postponed his departure, Mary Campbell died from a fever, putting a final end to Roberts plans for emigration. Perhaps most important of all, however, in July of 1786, Burns had succeeded in publishing the first book of his poems, the "Kilmarnock Edition", which was to become enormously popular and to launch the Ayrshire poet into the fashionable public eye with a level of celebrity that compares with a modern day pop star.