Journalism has always been characterised by unpredictability, freelancing and precarious employment, while it is little-known what exactly happens with precarious employment in journalism over time. To fill this research gap, this study set out to explore the career paths and structural context of precarious millennial journalists in Slovenia. In-depth interviews with stakeholders from media organisations were analysed in order to gain insight into the structural conditions of Slovenian journalism. With the aim of understanding what is going on with regard to the journalists’ career transitions, the authors conducted a longitudinal study of their careers and in-depth interviews with precarious journalists in 2017, and then again in 2021. The results have shown that the widespread professional image of journalists as watchdogs drew young people into the profession and reinforced hope labour. The journalists were motivated and willing to work overtime, thinking that a steady job was just around the corner. After years of hope labour, the structural conditions of journalism had deteriorated and the journalists realised that hope labour would not lead to a permanent contract at a media organisation. At that point, one group switched careers and took on public relations jobs, although they still considered themselves journalists and cherished the ideals of journalism from a far. The second group readjusted their lifestyle and economic interests for the sake of keeping a career in journalism, albeit outside of the legacy media structures and in precarious working conditions. The latter group has demonstrated that precarious and underpaid, yet very motivated journalists uphold journalism ideals.