// tl;dr A Proposition is a Way of Thinking // -/- This chapter is about type-theoretic approaches to propositional content. Type-theoretic approaches to propositional content originate with Hintikka, Stalnaker, and Lewis, and involve treating attitude environments (e.g. "Nate thinks") as universal quantifiers over domains of "doxastic possibilities" -- ways things could be, given what the subject thinks. -/- This chapter introduces and motivates a line of a type-theoretic theorizing about content that is an outgrowth of the recent literature on epistemic (...) modality, according to which contentful thought is broadly "informational" in its nature and import. The general idea here is that an object of thought is not a way *the world* could be, but rather a way *one's perspective* could be (with respect to a relevant representational question). I will spend the middle part of this chapter motivating and developing a version of this strategy that is, I’ll argue, well-suited to explaining clear phenomena concerning the attribution of perspectival attitudes -- in particular, attitudes towards loosely information-sensitive propositions -- with which extant approaches struggle. My overarching goal here will be to motivate a distinctive version of the "informational" approach -- the "Flexible Types" approach, which is based on the theory proposed in Charlow (2020). According to the Flexible Types approach, propositional attitude verbs are quantifiers over sets of possibilities, but a possibility is a type-flexible notion -- sometimes a possible world, sometimes a perspective, sometimes a set of possible worlds, sometimes a set of perspectives. -/- After introducing the Flexible Types approach, this chapter circles back to more traditional concerns for the analysis of propositions as types of possibilities -- Frege's Puzzle and the problem of Logical Omniscience. Here too the Flexible Types approach bears fruit. Although there are certainly significant differences -- I note some in the concluding section -- the gist of this theory is Hinitkkan or Lewisian in spirit (if not quite in letter). We can make progress on addressing the challenges for the analysis of propositional content in terms of types of possibilities, through empirically driven refinement of our notion of what kind of thing a "doxastic possibility" is. (shrink)