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The algorithm has proven to be a troublesome and ambiguous object, both as an everyday presence in our lives, but also as an object of study. For freelancers working through digital platforms, however, an awareness and sophisticated understanding of algorithms has become an increasingly essential aspect of carrying out their work. Here I argue that coming to an understanding of algorithms is also becoming essential for freelancers to retain agency in the 'gig economy'. Drawing on interviews with both workers and clients on the freelance labor platform Upwork, I outline how freelancers come to understand the programmatic operations of the platform, experimenting with its inputs and outputs, and become familiar with its patterns of surveillance. Furthermore, I explore how they use this understanding to strategically circumvent and repurpose these operations to their own professional interests. With this lens we can interrogate the developing relationship between inscrutability and agency amidst the proliferation of algorithms as mechanisms of organizing labor. Drawing on prior STS literature which has sought to embed the algorithm in its various socio-cultural contexts, I investigate how freelancers and clients enact algorithms in their negotiations and transactions, rather than allowing their work to be integrated into the automated protocols of the platform.