So often we are confronted with the question of whether to over or under communicate. Medical professionals are scrutinized for rushed care and poor lapses in judgment in deciding how to prioritize one patient’s matters over the others. In Day 1 of the 2016 Telluride Experience, there was clearly the spirit of a willingness to ask more questions and clarify when instructions or statements were unclear. Unfortunately, this is not necessarily as easily translatable into the clinical setting of our current medical reality. It is a shame that throughout our education before college, teachers, mentors, coaches, and parents would teach us to ask questions and to use our imaginations in the most explorative ways possible. But as we age, we let the experience, medical hierarchies and societal pressures prevent us from doing something so natural to us, asking a question and simply speaking up. From when do we let the fear and pressures of how others view us prevent us from doing what is necessary? From when do we let others dictate how we go about our own pursuits of knowledge and understanding? From when do we allow ourselves to compromise our integrity and bend our habits to conform? On the one hand, following the medical hierarchy provides the order and stability necessary to facilitate a chain of command and a set standard of training. But when does this system ultimately hinder our ability to make our own judgments and to be empowered from within? Why does the adage, “There are no stupid questions,” crumble in such a fashion in the medical world? What can we as future medical leaders do? Speak up and use our own gift of gab to gift the world with our own experiences, thoughts and innovations.