Autonomy is a core aspect of the labour process, working conditions, and the relationship between working conditions and well-being. Developments in techno-economic capacities, networked production, occupational structures, and organisational flexibility, have altered the dynamics of autonomy. High levels of work autonomy can now present counter-intuitive demands and contradictions which challenge the experience of self-regulation, discretion, and freedom at work - the Antinomies of Autonomy. In negotiating the decisive and interlinked post-industrial work bargains of effort, boundaries, and employment, different antinomies emerge which can present unique forms of stressors. The interrelated dynamics of the autonomy and antinomies within these post-industrial work bargains present difficulties for models linking working conditions and well-being outcomes (Bakker and Demerouti 2007, Karasek 1979, Siegrist 1996). The key mechanisms shaping the impact of work on psychological well-being go beyond the individual and a work 'place'. The thesis thus presents a sociological framework centred on a stressor (Wheaton 1999) - capability (Sen 1999, Hobson 2014) pathway. Employing a comparative case study method, the research draws from in-depth semi-structured interviews with IT workers in Ireland (n=17) and Denmark (n=14) to explore the antinomies, strategies and stressors of autonomous working lives and how they are shaped by different institutional contexts. The interviews involved psychosocial work environment and job related feelings surveys, alongside more detailed discussions of work and employment conditions in IT. The survey data shows an association between high autonomy and high demands for the Irish interviewees but not the Danish, and a surprising lack of feelings of excitement, enthusiasm, and calmness at work. The qualitative analysis identifies three mutually reinforcing antinomies of autonomy - interdependence, boundarylessness, and fusion - occurring within the labour process, working conditions, and the employment relationship respectively. The strategies and stressors emerging from these conditions are based on the 'capability sets' available within each institutional context. The analysis shows how Danish interviewees drew on more collective and institutional resources and norms in developing working life strategies. The Irish interviewees described strategies sourced and sustained mainly at the individual level. The thesis illustrates the complex interplay of post-industrial work bargains, the antinomies of autonomy, institutional capabilities, and the social structure of stressors of working life.