A lot of programming research shares the same basic motivation: how can we make programming easier? Alas, this problem is difficult to tackle directly. Programming is a tangle of conceptual models, programming languages, user interfaces and more and we cannot advance all of these at the same time. Moreover, we have no good metric for measuring whether programming is easy. As a result, we usually give up on the original motivation and pursue narrow tractable research for which there is a rigorous methodology. In this paper, we investigate the limits of making programming easy. We use a dialectic method to circumscribe the design space within which easier programming systems may exist. In doing so, we not only bring together ideas on open-source software, self-sustainable systems, visual programming languages, but also the analysis of limits by Fred Brooks in his classic “No Silver Bullet” essay. We sketch a possible path towards easier programming of the future, but more importantly, we argue for the importance of proto-theories as a method for tackling the original motivating basic research question.