Awareness and management of the risk of failing to encounter lift is fundamental to thermal soaring. When the weather changes or a thermal is missed the pilot may be exposed to a greater risk of landing out. In these situations the pilot may need to alter strategies in order to minimize risk exposure at the expense of speed, often referred to as "gear shifting." In this work, we explore several models to explain why small changes in the environment can cause large changes in risk exposure, requiring this shifting. We also examine several flight strategies in simulation to define the relative risk and reward for adopting various levels of risk tolerance and for failing to "shift gears" when the risk of landing out increases.