This manuscript was originally delivered as the 2019 presidential address at the Ohio Valley Philosophy of Education Society annual meeting in September of that year. In this address, the author briefly distinguishes the Deweyan understanding of "impulsion" from that of "expression" as he discusses them in" Art as Experience." Following that, the author takes up a general etymological/conceptual reminder as to the role that any medium plays given the space mediums occupy in the act of human expression. The author then extends the discussion of mediums and how they operate in the human endeavor of expressing meaning-expression being one of those endeavors that might make life worth living--by way of Neil Postman's contention that communication technologies as mediums of expression are inherently and metaphorically ideological; and, as such, dictate in large part what can and what cannot be meaningfully expressed. The author concludes by pointing to some serious epistemological dangers given the nature of human expression, contemporary media, and any medium's role in that expression-- particularly political expression--and the educational implications those dangers hold given pragmatic understandings of truth.