UC Santa Barbara

Prevailing depictions of retirement conceptualize it as the end of a person’s working life. However, with increasing longevity, aging populations, and shifting social policies in industrialized nations, millions of older adults are working beyond the years typically associated with retirement. In formal organizational employment, a career model that positions retirement as the complete end of work remains prevalent, resulting in limited options for older workers. At the same time, new employment arrangements are emerging, spurred by digital technologies, including online labor platforms. Thus, a growing number of older workers are retiring from full-time organizational employment and continuing to work through platforms. On the surface, platforms promote autonomy, flexibility, and opportunity. However, they introduce new challenges through algorithmic management, limited worker protections, and a lack of direct interpersonal interaction. Therefore, this dissertation examines whether and how online freelancing platforms could be viable work arrangements for the growing population of older workers. This dissertation features chapters based on a qualitative case study of retired workers (aged 55+ years) who left formal organizational employment and continued working through Upwork, one of the largest online freelancing platforms. The chapters draw on data from 180 informants, including interviews, online observations, participant diaries, and archival materials from Upwork’s platform. In the introductory chapter (Chapter 1), I develop a theoretical framework to define a new construct, ‘retirement-work orientations,’ which amends the notion that retirement and work are in opposition and conceptualizes the nature of work in later life on its own terms. The first empirical chapter (Chapter 3) examines how retired workers encounter a ‘cold-start problem’ of having to build their reputations anew through ratings on the platform. The second empirical chapter (Chapter 4) demonstrates how retired workers use platforms to navigate the liminality of retirement while continuing to engage in paid work. The third empirical chapter (Chapter 5) compares retired workers transitioning to platform work with those at earlier career stages. I find that under the same precarious conditions, workers experience precarity differently depending on their biographical foundations. For scholars studying careers and the future of work, this dissertation shows how online freelancing platforms, as an emerging organizational form, offer both generative possibilities and constraining dynamics for older workers. Indeed, as work becomes increasingly mediated by platforms, algorithms, and other digital technologies, attending to the distinct vantage point from which older professionals approach their work, shaped by their accumulated experience and specific needs, preferences, motivations, and circumstances, is critical for organizing amid an aging workforce. For scholars studying the future of work and careers, this dissertation shows how online freelancing platforms, as an emerging employment arrangement and organizational form, offer both generative possibilities and constraining dynamics for older workers. Indeed, as work becomes increasingly mediated by platforms, algorithms, and other digital technologies, attending to the distinct vantage point from which older professionals approach their work, shaped by their accumulated experience and specific needs, preferences, motivations, and circumstances, is critical for organizing amid an aging workforce.