In this article, I use alter egoing as a heuristic, a method for solving the problem of the evolving alter egos of Black women in popular music. When alter egos are analyzed through this lens, the refashioning of artistic imaginaries become legible as intellectual labor. The intellectual labor that Janelle Monáe primarily provides are critiques of notions of womanhood and Blackness in the United States. I understand Monáe’s alter egoing as a reaction to the affective political strategies mobilized in US electoral politics. Former President Barack Obama developed an affective strategy based on his personal brand of optimism, first presented in his book The Audacity of Hope (2006). He developed his signature optimistic politics while he was a senator and he continued to promote his “audacious hopefulness” into his 2008 presidential campaign. Former President Donald Trump’s 2016 presidential campaign also utilized an affective political strategy, as he rallied his supporters around culturally white (male) nostalgia with the cry, “Make America Great Again.” I track the affective evolution of Monáe’s alter egoing from pessimism to optimism in the context of the anti-Black populisms of the post-Obama era (2016–), culminating in a close reading of her 2018 album, Dirty Computer. In identifying Monáe’s troubled relationship with notions of normative identity through her first alter ego, I evaluate the relevance of posthumanism and Afrofuturism, which scholars have used to critique American notions of race, gender, and sexuality. In analyzing the shift in affect from her first alter ego to her most recent, I detect in Monáe’s alter egoing a critical optimism, a disidentifying strategy that begins to take shape in Dirty Computer.