Recent transformations in employment have destroyed post-1945 settlements involving standard work contracts and the social protection of Europe’s working populations. Employment restructuring, precarious jobs, and in-work poverty require new approaches to reconcile current working practices with social justice. Amartya Sen’s capability approach promotes a person’s choice to live the life she has reason to value as the means to reconcile personal freedom with economic well-being. The content and methods of such choice are founded on informational bases of judgement in justice, themselves the product of collective democratic deliberation that achieves compromise between varying views and forms the essential foundations within which choice can be realized. Such informational bases are necessarily open-ended, as both personal orientation and circumstance vary by place and time. Linking the capability approach to the economics and sociology of conventions (EC/SC or convention theory) promotes a normative critique of current social and employment policies (principally, but not solely, labor market activation), their mode of assessment (new public management) as well as labor law, employers’ strategies and deliberative democracy in decision-taking in terms of whether (or not) personal capabilities are fostered by prevalent practices.