Research on digital inequality suggests that digital skills are integral to participation on gig platforms. Focusing on the case of online freelancing, this article asks what such skills look like and how gig workers translate them into opportunities. Drawing on semi-structured interviews with 21 U.S. online freelancers, I identify moments in which participants approach the gig platform differently because of their digital skills. I find that digital skills enable online freelancers to (1) optimize their use of platform tools, (2) construct alternative pathways when existing tools malfunction, and (3) imagine and blaze new paths that go beyond the platform's current functionality. These findings suggest that, in the volatile context of gig platforms, digital skills entail not only the ability to leverage platform tools as designed but also the capacity to creatively navigate situations in which the online environment changes, breaks, or proves inadequate for their needs. Finding and completing work through online platforms is becoming more popular. Drawing on interviews with so-called online freelancers, this study explores what skills are involved in using these platforms effectively. These digital skills allow people to find appealing work and determine how to apply more efficiently. More digitally skilled individuals are also better prepared to handle unexpected situations that may arise in their work on the platform. Additionally, online freelancers use their skills to devise creative ways to meet their needs when platforms lack the functionality they require. Ultimately, given that the platforms provide little support, digital skills are essential to making a career out of online freelancing.