The traditional lines between contractors and employees are fading fast as outsourcing continues to gain popularity. The “gig” economy leads people to pursue freelance careers, working several jobs or maintaining a “side hustle.” Technological advancements allow more flexibility in where, when, and how jobs are completed, further blurring traditional distinctions between contractors and employees. Yet the risk associated with misclassifying an employee as an independent contractor can be catastrophic for an organization.