Pilots make bad decisions, leading to landouts and accidents. Understanding how people process information and how outside influences can interfere with this operation can help pilots make better choices. While soaring, pilots are presented with a nearly unmanageable amount of information. Pilots work around this problem with rules-of-thumb and leaning on past experience. Past experience leads to intuitions and emotions, which are critical for effectively processing information. These factors contribute toward a general decision-making engine that is driven by a pilot’s priorities, situational awareness, judgments, decisions, and their actions. Failures in this process lead to landouts and accidents. We will survey how several systematic biases distort judgment. First, we will discuss how loss and regret aversion affect sporting and safety decisions. These biases can paradoxically lead to “conservative” pilots making “aggressive” safety decisions. Next, we will discuss how the certainty effect contributes to sub-optimal final glide planning, how to optimize one’s mental state when trailing or leading while racing, and how experience can contribute to accidents through the systematic under-weighting of risk.