The ideal of comfort affects how and what we think, but how much does it affect our willingness to change-both outside and inside our minds? What is the role of comfort in the planning discipline? Building on these questions, this chapter explores the paradox framed by the simultaneous need for the stability of comfort-seeking practices and the openness towards uncertainty and change that requires a certain level of discomfort. In this conversation, the authors centre the discussion around the concept of safe uncertainty as a practice of contesting traditional norms, changing decision-making tempos, and embracing interpersonal interactions and inclusivity, underlining the challenges set by the current projectification of planning.