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“Experience,” one of Emerson’s most complex essays, is typically understood to perform a work of mourning for his son Waldo, in the wake of whose death he also revisits his philosophy and reformulates some of its major propositions. Located at the intersection of the personal and philosophical, the essay is thus seen as outlining Emerson’s philosophy of the experiential predicated on disappointment, loss and death. I question that understanding by arguing that the second part of the essay insists on an affirmative philosophy to be formulated despite loss and death. In investigating just how this affirmation of life in the midst of unhappiness is imagined, I offer an outline of Emerson’s ontology and propose that his critique of pessimism in the essay’s second part introduces also an affirmative ethics, a set of practices that would take us out of sorrow and lead toward prudence.