Pessimism as a living philosophy of life at any rate cannot be considered as a proposal with a candid appeal. Majority times it is by default that a philosophy is forced upon by life-experiences. Ultimately choice of a specific philosophical outlook as a guidance or route to happiness is mostly an outcome of one’s own compromises in life. It goes without dispute that only a select few philosophers could master courage to handle Pessimism as a philosophy. Needless to say Schopenhauer’s approach is indeed a unique one. Embracing reality needs an upright nature and further transcending over it to guide humanity requires the strength of purpose. It is an uphill task. The paper attempts to show how Arthur Schopenhauer dealt with pessimism at the initial stages and later drew philosophical tenets out of this behavioral science. In addition Schopenhauer’s treatment of this subject just does not include only exposing the negativities of life but providing solution through ‘Nirvana’ philosophy.