Among the challenges of poststructuralist thought has been the demand that we acknowledge a kind of philosophical emptiness which many feel accompanies the perceived decline in foundationalist thought. By looking more closely at Barthes and Baudrillard’s writing on meaning, writing, language, truth, and the real, we can come to a better understanding of the emergence and implications of the poststructural challenge. The paper argues that Barthes’ and Baudrillard’s writing on these five key concepts can lead us to a more liberating conception of thought and contribute to our individual effort to become more challenging thinkers. This paper also (unavoidably) points to several points of convergence and divergence between Barthes and Baudrillard.