MAKING YOUR BED AS AN INDEPENDENT CONTRACTOR BUT REFUSING ‘TO LIE ON IT’: FREELANCER OPPORTUNISM TUMO CHARLES MALOKA* Associate Professor, Department of Mercantile and Labour Law, University of Limpopo CHUKS OKPALUBA** Research Fellow, Centre for Human Rights, University of the Free State Abstract The ‘freelancer migraine’ demonstrates that the long-standing and deeply embedded distinction between employment and independent contracting (self-employment) is challenged by the reality of the contemporary work environment which does not readily conform to such binary categories. The inescapable inference from the freelancer jurisprudence is that a significant number of the self-employed are in a position of economic dependence analogous to subordinate employees in that many, if not all, lack distinguishing features of entre- preneurship: ownership, autonomy, or control overproduction. Somewhere in between genuinely subordinate workers and genuinely independent entrepreneurs, a third category is emerging — that of workers who are legally independent (ie, self-employed) but economically dependent. The freelancer decisions provocatively raise fundamental questions about the opacities of form engendered by the fragile boundary between genuine entrepreneurial self-employment, dependent self-employment, and disguised employment. Rather than ushering in the fabled entrepreneurial independence, for many of the recruits into the ranks of freelancers, self-employment often heralds a descent into a state of precarity. I INTRODUCTION Writing in 1944, United States (‘US’) Supreme Court Justice, Wiley Blount Rutledge, observed that: * BA LLB LLM (UCT) LLD (UFH). ** LLB LLM (London) PhD (West Indies). Thanks to the reviewers for careful reading, thoughtful feedback, and editorial suggestions. The usual disclaimer applies. 54 (2019) 31 SA Merc LJ 54 © Juta and Company (Pty) Ltd