Scotland’s economic capacity to prosper independently of Britain has become a key political issue, dominating the independence referendum of 2014 and continuing to influence British politics since. Often, that debate centres on the contested terms of how we imagine or construct Scotland as an economic entity. Thus, it offers a major opportunity to study the broader issue in critical social science of how economies are “imagined”. However, to date most studies of Scotland’s economy comes from the discipline of economics or from the policy profession. This study aims to address this gap. It highlights the comparatively recent history of professional interest in the Scottish economy; asks what these professionals are “doing” or “constructing”; and looks at how this influences Scotland’s conformity with and deviance from mainstream British politics. Using Jessop’s concept of “economic imaginary”, and drawing on cultural political economy, I thus examine the current Scottish economic debate’s conditions of possibility. These include the emergence of British regional policy, the discovery of North Sea oil, discourses of competitive regions in Europe and the elective affinities between devolution and “enterprise”. I pay particular attention to a general shift in attitudes away from top-down plans to equalise growth across Britain to a focus on the “spirit” of enterprising regions. My research used critical discourse analysis to analyse 100 key documents that played important roles in or highlight key issues in Scottish economic development. I also drew on 23 in-depth semi-structured interviews with professionals and journalists. My original contribution is to examine the path-shaping role of Scotland’s economic imaginary, how choices were made and how alternative paths were closed off. By looking at one contested case, we can gain insights into broader imaginative processes in national and regional economies.