How has artificiality been imagined and circumscribed in works of fiction? For this paper, I answer the question by utilizing three of Miguel de Unamuno's early works to explore artificiality and authenticity. From "Amor y pedagogia" ("Love and Pedagogy" [LAP]) to "Del sentimiento trágico de la vida" ("The Tragic Sense of Life" [TSL]) to "Niebla" ("Mist"), Unamuno explored questions about being, not being, and the possibility of 'being-beyond' that situated artificiality in relation to learning and schooling. I argue that philosophy of education can learn from Unamuno's use of chiasmus and irritation to question artificiality.