 Assigned to Rev.Thomas Reddall at Campbelltown as a labourer (though he was a clerk by calling), and then to Major George Druitt at Mount Druitt, probably as a schoolmaster, Riley was granted his Certificate of Freedom in 1831.Through the 1830s and early 1840s Riley published verse – mainly comic and satirical – in Sydney newspapers, either anonymously or under various pseudonyms including J. R., Dick Lightpate, A Child of Song, Owen Bulgruddery, Felix M’Quill, Caleb Menangle and Felix.