Abstract
This paper develops two theses and one suggestion. The first thesis concerns how to reason about the problem of philosophical progress. Chalmers (2015) and Dellsén et al. (2022) proposed frameworks to reason about this problem. I argue that these frameworks have limits and develop an alternative. Having done this, I put my proposed framework to the test. That is, I use it to analyse the views held by Kant in the first critique and Wittgenstein in the Tractatus. The second thesis concerns the relations between these works. My proposed framework makes evident that, for all their differences, Kant and Wittgenstein gave similar answers to the problem of philosophical progress. They both claimed that philosophy has been very unproductive for much of its history and proposed methods to fix this. My suggestion is that this might be a recurring pattern in the history of philosophy, which perhaps could help explain why, to this day, there is so much pessimism concerning philosophical progress.