My ongoing body of work, <em>The Right Brain of Darkness</em>, 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, <em>The Left Hand of Darkness</em>, as a transfeminist text. <em>The Left Hand of </em><em>Darkness </em>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 <em>The Left Hand of Darkness </em>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. <em>The Right Brain of </em><em>Darkness</em> 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.