Recent market structural trends, like the growing importance of the service sector and the evolution of contractual arrangements in favour of franchising and outsourcing, have left many workers standing uncomfortably in the ‘grey’ area between employment and self-employment. As shadow-economies emerge, online platforms that arguably exercise labour-brokering functions become outlaws in a high-tech Wild West, shifting the risk of running a business to workers. And yet, the ‘gig economy’, being the latest expression of laissez-faire capitalism, brought to the surface a long-standing issue, namely the inadequacy of our taxonomy to successfully incorporate multilateral contractual relationships. Thus, in an era when self-employment is on the rise and ‘own-account workers’ could qualify either as ‘workers’, ‘undertakings’ or ‘service providers’ for the purposes of EU regulatory provisions, it becomes vital that the Union revisits the relationship between the Free Movement and Competition law provisions. My PhD aims to respond to these challenges by coming up with a dynamic and holistic theorization of the basic characteristics of dependent employment. Arguing against the general trend towards work flexibilization and in favour of a fair mutualisation’of risks, I will examine whether the new European ‘worker’ definition can be extended to capture not only those in quasi-dependent, marginal working arrangements, but also those who are genuinely self-employed with no staff.