The paper attempts to examine what is by all accounts a self-styled approach to contemporary existence, borrowing from Claire Colebrook's 2017 essay on Bernard Stiegler's so-called 'curious problem of range'. Subsequently, we tackle Yuk Hui's interpretive reading of Stiegler's analysis of retentional digitality. Hui promotes the idea of archival metaphysics to overlay Stiegler's concept of tertiary retention with tertiary protention. However, Stiegler's reformulation of Kant's aesthetics already addresses these concerns: the problem of range that his works continually provoke and the self-inscriptive conditions of writing that limit the examination of this range to the paradox of différance. Stiegler assigns the task of unraveling this range in question to the amateur, vis-a-vis the critic's typical role in the conduct of critical reason. For Stiegler, the amateur is the full achievement of aesthetic judgment, essential to education and culture formation.