This article reflects on some of the major changes in the ways that people are working today, changes often driven by a preference for greater autonomy and choice, but also to work on a sharing, collaborative or networked basis. Many of the growing numbers of independent professionals are attracted by these ways of working. Developments in Information and Communication Technology have been critical, especially in enabling services, including professional services, to be delivered via internet platforms. This has created, in effect, new forms of intermediation and increasingly complex work relationships. These developments have often proved very controversial, as instanced by the disputes surrounding Uber, the international, internet-based taxi provider. Many of these changes also raise issues of accountability and work quality, along with creating new patterns of work relationships. Inevitably, the changes also highlight the role of regulation, which is the main focus of this article. The topic is explored against a backdrop of much recent deregulation, challenges to so-called ‘red tape’ and laissez faire policies. The myriad of disputes and litigation involving Uber is examined and reflected upon. There are, of course, many differences between the taxi drivers of Uber and the designers, journalists, engineers and consultants, typical of independent professional working, but there are also some key parallels and experiences that provide a cautionary tale!