This chapter discusses the democratic individuality as an anti-egotistical aspiration. It shows democratic individuality as the most powerful effort undertaken by any kind of individualism to battle egotism. The subject of egotism as loss of self pervades the work of the theorists of democratic individuality, Emerson, Henry David Thoreau, and Walt Whitman. Egotism is the comprehensive term for these and related vices, which existed well before any kind of individualism emerged. In civilization, each soul is inevitably afflicted, as Rousseau rightly taught. Emerson, Thoreau, and Whitman all help us think about self-loss and its connection to egotism, and they do so as defenders of individualism, as philosophers of democratic individuality. In contrast, some kinds of individualism espouse self-concern, care of the self, and the effort to take oneself seriously in distinct ways. Self-insistence is not the same as self-concern; and each goes very well, goes best, without the other, paradoxical as that may sound.