This chapter explores the philosophical positions of Friedrich Nietzsche and Sri Aurobindo in relation to the contemporary discourse on transhumanism. It addresses the core ethical question: Should humanity seek to overcome itself through technological or biological enhancement? While transhumanism envisions the transformation of the human condition through technology, Nietzsche and Aurobindo offer alternative paths rooted in inner transformation and consciousness evolution. Nietzsche and Aurobindo envision human overcoming as an existential or spiritual project. For Nietzsche, the Übermensch emerges not through the eradication of suffering but through its sublimation into strength, art, and affirmation. For Aurobindo, true transformation proceeds from a supramental consciousness that transfigures the body from within, not through external intervention. Both thinkers resist mechanistic materialism and call instead for a revaluation of the human grounded in psychic, moral, and spiritual evolution.