The works of Joseph A. Goguen and Samuel R. Delany address wide arrays of "big" issues in philosophy: identity and qualitative experience, semiotic representation, and the divergence between meaning in formal systems of understanding and in everyday lived experience. This essay attempts to draw out some of the parallels between the works of these two authors, in particular regarding metalogic, qualia, and identity, using illustrative examples from the works of both authors. Their works exhibit parallel dual strands: (1) a desire to rigorously and precisely map out these fundamental issues, and (2) a desire to acknowledge and embrace the ambiguities of phenomenological experience and its divergence from any formalizable theory. In the end, addressing such a wide range of issues has required both authors to develop and adopt new discourse strategies ranging from rational argumentation to mathematics, from religious and philosophical commentary to speculative (science) fiction and poetry.