Everything starts with trust. It is the foundation of personal and professional relationships, leadership abilities, innovation, collaboration, business stability, entire nations, and much more. And often, trust is enough. However, misplaced trust—trusting the wrong thing, the wrong amount, or at the wrong time—can have significant, negative consequences. But how can we know when trust is enough? And what do we do when it is not? By practicing skepticism! Skepticism is frequently equated with cynicism or pessimism, and skeptics are often seen as suspicious or even jaded. But, real skepticism is actually a neutral stance that suspends belief until justified evidence is available. Healthy skepticism is more closely aligned with curiosity and caution. And it can help us avoid negative consequences and move forward when trust is not enough. Practicing skepticism involves fact-checking, being aware of biases, asking good questions, and much more. And it is all especially relevant with the rise of Artificial Intelligence, a powerful yet complex technology. Understanding AI and practicing skepticism can help us use it effectively and safely. Join me as I explore trust, promote skepticism, offer ways to develop a skeptical mindset, and show how these ideas apply to AI and other contexts by providing practical tips to better navigate our world.