Generative AI is promoted as a way to enhance knowledge work, yet its benefits and drawbacks fall unevenly across the workforce. Freelance and gig workers, who commonly lack the upskilling pathways available to traditional employees, face heightened risks to both skill development and job security as AI adoption advances. We review empirical evidence on AI's impact on knowledge-worker workflows and upskilling, then predict the primary and downstream effects of AI adoption among clients and workers in the freelance economy. We anchor this in two cases of the same shift, machine-translation post-editing and software development. We argue that freelancers are the leading edge of a change that also reaches salaried HCI practitioners, and we close with questions for the platforms and clients that mediate this work, and for HCI researchers.

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