There is a strong correlation between uncertainty and the personal growth of the people who navigate unchartered waters. Often these leaders discover skills they never knew they possessed as they readjust their lenses to pursue a different perspective. This chapter discusses a variety of methods, including improvisation and double-loop learning that can help adapt a person’s perception of the current environment. The paradox of change is also explored to learn what enables some people to create more value from the same resources within similar scenarios than others.