This work interrogates the seeming ambivalence between Arthur Schopenhauer's existentialist pessimism and his advocacy for artistic, moral and ascetic forms of awareness, as means of managing the absurdities and frustrations of life. The objective of this work is to discover whether or not his apparently orthogonal positions can be reconciled in any way at all, and what that might portend for the contemporary philosopher. Schopenhauer's metaphysics and philosophy of nature led him to the doctrine of pessimism: the view that sentient beings, with few exceptions, are bound to strive and suffer greatly, all without any ultimate purpose or justification and thus life is not really worth living. Arthur Schopenhauer was among the first 19th century philosophers to contend that at its core, the universe is not a rational place. Inspired by Plato and Kant, both of whom regarded the world as being more amenable to reason, Schopenhauer developed their philosophies into an instinct-recognizing and ultimately ascetic outlook, emphasizing that in the face of a world filled with endless strife, we ought to minimize our natural desires for the sake of achieving a more tranquil frame of mind and a disposition towards universal beneficence. Often considered to be a thoroughgoing pessimist, Schopenhauer in fact advocated ways to overcome a frustration-filled and fundamentally painful human condition. He believed that the "will-to-life" (the force driving man to survive and to reproduce) was the driving forces of the world, and that the pursuit of happiness, love and intellectual satisfaction was essentially futile and anyway secondary to the innate imperative of procreation. This essay argues that phenomenologically, Schopenhauer had an “existentialist” orientation towards the spatio-temporal world that informed his pessimism, but also engenders further questions regarding the actual sincerity of his mental commitment to such a position.