We report findings and discuss implications from a panel study of 68 U.S.-based online freelancers. These findings emerge from analysis of two rounds of data collection: The first round straddled the arrival of COVID in 2020 and the ensuing pandemic-inspired economic downturn. The second round, from early 2021, provides insight into how online work changed in the following months. We see online freelancing as a window into one future of work, one where the market, not the organization, is the primary structure of the worker-employer interaction, mediated by digital platforms and relying on both algorithms and interaction between parties. Our purposive sampling framework, multiple sources of data, and longitudinal design provides for both empirical and conceptual insights into the occupational differences and arrangements of freelance workers. Findings make clear: 1) these workers value job flexibility even as workers experience diminishing flexibility; 2) occupation mediates worker’s experiences; and 3) gender differences impact the outcomes of this form of work. These findings also highlight the precarity of online freelance work, raising questions about both online freelancing, and market-based labor structures more generally, as a sustainable source of work or viable career path.