Effective future leadership—from the most intimate and personal to the most encompassing—hinges on our ability to better understand, tolerate, and manage uncertainty. Our world is becoming not just less certain, but often frighteningly so. New uncertainties have multiple origins. Today’s rapidity of technological change, how globalization challenges culturally-specific assumptions, and the risks that accompany the rewards of progress, from environmental degradation to the potential for ever-more-dangerous weaponry provide the most obvious new uncertainties. But ultimately even more important are deeper changes that today reorder human identity, relationships, and social structures. The concept of Cultural Maturity helps us make sense of today’s new uncertainties. It also provides guidance for confronting them. And it goes further. It proposes that while much in today’s new uncertainty simply makes life more difficult, the larger portion ties directly to the possibility of living more creative lives and gaining new and deeper understandings of order and purpose.