Was Kleist a philosophical poet? Or were his early forays into philosophical essay writing - as often claimed - nothing more than student exercises in the style of the popular philosophy of his time? Contrary to the prevailing opinion, this study shows that Kleist's turn to art neither marks a break from philosophical reflection nor does he transform into an anti-Enlightenment advocate of feeling during his life crisis of 1801 - that famous "Kant crisis" - who acts spontaneously and unreflectively against all civilizational constraints. The central thesis, however, is that Kleist addresses the problem of mediation between moral claims and human capabilities both in his essays and letters as well as in his literary works. His writings reflect the question of the extent to which the anthropological conditions of motivation - of feelings.