This chapter addresses how cognitive flexibility enables an individual to respond adaptively to new situations and respond appropriately to any situation. Interrupting automaticity avoids being trapped in mindsets that foreclose generating new options; avoiding reductive bias reduces the tendency to oversimplify and turn dynamic processes into fixed objects and make complex interactions linear; avoiding functional fixedness reduces the tendency to apply the same solution to different situations; and cognitive connectivity opens up to new approaches in which mental models can be transformed, schemata reorganized, and cognitive bridges built between previous expertise and new situations. This kind of cognitive flexibility enables individuals to respond and adapt to the new situation into which they are moving. This is discussed in light of the retrospective interviews with twenty-four elite performers in three domains (business, sports, and music) who successfully and repeatedly transitioned to higher positions within their field.