My ongoing body of work, The Right Brain of Darkness, celebrates Ursula K. LeGuin’s brave use of imagination and considers in earnest willingness to fail essential in any attempt to evoke new and undetermined ways of being. With this project, I am claiming LeGuin’s classic feminist novel, The Left Hand of Darkness, as a transfeminist text. The Left Hand of Darkness is a sci-fi novel published in 1969. The story takes place on a planet with an androgynous human population. Periodically these subjects go into heat, developing sexual organs based on their flirtations. As a transgender woman, reading The Left Hand of Darkness felt like a gift. Still, the novel’s deconstruction of gender is awkward and dated, including LeGuin’s insistent use of male pronouns for genderless people. The Right Brain of Darkness centers imagination as a radical tool. We must be courageous enough to imagine other worlds and ways of being. And we must be willing to make mistakes, get called out, and try again.