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In this chapter, we theorize about online freelancers’ approaches to work flexibility. Drawing from an ongoing digital ethnography of US-based online freelancers pursuing work on digital platforms, our data question the common conceptualizations around the flexibility of online freelancing. We posit that the flexibility of where to work, not when to work, is the most important attribute of their work arrangement. Our data show (1) the online freelancers in our study prefer the stability and sustainability of full-time work over freelancing when both are offered as remote options; (2) full-time remote employment increases these workers’ freelancing control / flexibility; (3) these workers keep freelance work options open even as they transition to more permanent full-time work arrangements. We discuss how these findings relate to workplace culture shifts and what this means for contemporary working arrangements. Our insights contribute to the discourses on knowledge-based gig work and for what it means to study individuals online.

Our prior work has identified a trade-off that new entrants face in obtaining favorable market reception, whereby initial entrants suffer from a deficit of legitimacy whereas later entrants suffer from a deficit of authenticity. This research has also proposed that a single mechanism is responsible for this trade-off: the tendency for customers and other stakeholders to assess the entrant's claim to originality based on the visible work that it has done to legitimate the new product or organizational form. This chapter extends and deepens our understanding of such “legitimation work” by showing how it can illuminate cases that seem in the first instance to defy this trade-off. In particular, we focus on two “off-diagonal” cases: (a) when, as in the case of “patent trolls” and fraudulent innovators, early entrants are viewed as inauthentic despite having a credible claim to originality; (b) when late entrants, as in the case of Dell Computers, mechanical watches and baseball ballparks, are viewed as authentic despite obviously not being the originators. We clarify how each off-diagonal case represents an ‘exception that proves the rule’ whereby audiences attribute authenticity on the basis of legitimation work rather than on the order of entry per se. The last case also leads to an opportunity to clarify why “cultural appropriation” can sometimes project authenticity and sometimes inauthenticity, why audiences bother to make inferences about a producer's authenticity on the basis of visible legitimation work, and why legitimacy is a universal goal of early movers whereas authenticity varies in its importance.

Cultural criminologists have long been interested in the politics of crime and deviance, whether that be in relation to youth subculture resistance or the social reaction to transgression evident in the media construction of folk devils and moral panics. While contemporary ‘new’ cultural criminology continues to be focused on the situated experience of deviant ‘edgeworkers’, this chapter argues cultural criminology’s concern with the crime-media nexus provides particularly fertile ground for exploring insights provided by activists, academics, professional journalists and citizen journalists around informal interventions on formal criminal justice processes using social media and digital technologies. Drawing on examples from a burgeoning body of crime-media research, the chapter makes a case for ‘cultural criminology activism’, which, like activist criminology, is consciously disengaged from mainstream criminology’s alignment with the neoliberal-carceral state and its reformist agenda.