This article attempts to reconsider and re-evaluate the often misunderstood and mis-conceptualised notion of "progressivism" within education by examining it through the lens of intentionality, specifically the textual kind prescribed by Quentin Skinner in his seminal work "Visions of Politics" (2002). Locating and explicating his ideas will therefore form the first part of the article. In particular, there will be an examination of his two key analytical concepts, locutionary meaning and illocutionary force, which will act as the methodology for the analysis. The second part of the article will examine how writers of the past have tended to equate the term "progressivism" with "progressive schools", seeing the concept as floating through time, independent of human agency. There will be a brief discussion on the problems of misconceiving progressivism in this way. To fulfil its chosen aim therefore, the article will use as its focus two contemporaneous educators from the past who have often been seen as fitting into the same, linear progressive tradition: Susan Isaacs and A.S. Neill. The article will demonstrate in its final part, through a Skinnerian examination of one of each of their key texts, how far from fitting into a homogenous progressive discourse Isaacs and Neill were when it came to their intentions and understandings in writing. (Contains 75 footnotes.)