Many companies, particularly in the Gig Economy, have been the target of lawsuits alleging that they have misclassified workers as independent contractors rather than employees. These issues often present bet-the-company litigation, with billions of dollars and the companies’ very business models at stake. Although there is near-universal recognition that the division of workers into two rigid categories creates a host of problems because it is based on antiquated notions that fail to map cleanly onto the modern economy, legal scholarship to date has failed to adequately grapple with the existing employment case-law to propose a new way forward. This Article does so by exploring the history of both the Gig Economy and the contractor-employee bifurcation, drawing on insights from their intersection to propose a new test for properly categorizing workers. In doing so, it outlines the contours of an intermediate category of worker, the “independent employee.” Although many have suggested that a new category of worker would be beneficial, they have generally failed to explain what such a category would look like in practice. This Article fills that void by providing a functional framework for both how to identify independent employees and determining the legal protections and benefits that they should be granted.