This chapter examines how, in the early 1900s, Irish journalists organised themselves into an association that examined contentious issues such as salaries, employment conditions, the social status of journalists, the place of women in journalism, and whether trade unionism was appropriate for journalists. Against the backdrop of the Great Lockout, the First World War, and the 1916 Rising this nascent organisation (the Irish Journalists’ Association) allowed journalists to discuss contentious issues amongst themselves. However, the development of the association was hampered by divisive debates about the role of journalists in society and the bid for national independence by physical force.