Therapists are conduits of possibility as we hold a vision of what is possible for people who come to us seeking support and change. Gender specialists help transgender, nonbinary, and gender-diverse (TGNB) people to increase the possibilities in their lives. Therapists facilitate positive change—on an individual level, through therapeutic practice, and on a macrolevel, by being involved in the community of psychotherapists and in the field of transgender health. As we approach our work, we reflect upon the limitations of our knowledge and vision to be realistic and to allow for possibility. We respect uncertainty on an individual level because people are complex and change over time as the world around them changes, and we respect uncertainty on a cultural level because the language and concepts of gender change and evolve across time and place. Cases are presented to illustrate the use of psychotherapy to address uncertainty and create possibility for TGNB people.