Although the literature on critical thinking and transformative learning has remained relatively distinct, they have both emphasized the importance of working through and resolving states of doubt. There has been less focus, however, on how we can bring ourselves from a confirmed belief to a position of doubt. This is a foundational skill. Without it, the possibility for intellectual and personal growth is limited. In part one, I focus on critical thinking to investigate what ability and/or disposition can help thinkers arouse a state of doubt. I first consider traditional dispositions of critical thinking, specifically reflection and open-mindedness, and argue that they are largely ineffective as they do not confront the problem of cognitive bias. I then propose perspective-taking as an essential tool to bring about a position of doubt. In part two, I examine leading theorists in transformative experience, transformative education, and transformative learning, who have also largely neglected perspective-taking. I illustrate that perspective-taking can initiate some instances of transformative learning and thereby provides a connecting point to critical thinking. Nevertheless, when engaging with perspective-taking exercises, I argue that instructors ought to prioritize the development of students' critical thinking skills. In part three, I focus my discussion on incorporating nonfiction perspective-taking readings into university course syllabi as a way to develop students' critical thinking while creating the conditions for transformative learning.