In this article, Morten Korsgaard and Mathias Aldinger examine the educational thinking of Hannah Arendt and accompany their analysis with an educational reading of Søren Kierkegaard's "The Seducer's Diary." The authors argue that their readings of Arendt and Kierkegaard point us to a pitfall in how we often approach the educational process: expecting the generation that is coming of age to satisfy the desires of the older generation. This expectation, which pervades present educational reform efforts, undercuts the possibility of education for (existential) freedom and, indeed, serves to manipulate the young into adopting the ideals and desires of the older generation. Reading "The Seducer's Diary" educationally allows us to interpret Johannes as a (mis)educator of Cordelia in the mold of the progressive and instrumental educators that Arendt critiques in "The Crisis in Education." In this way, Arendt and Kierkegaard alert us to the perennial paradox of educating for freedom without attempting to determine how this freedom is to be lived out and thus undermining the endeavor in advance.