An insightful look at how human beings are the walking definition of risk and how the consequences of our choices in any adventure or challenge can impact our overall well-being. The adventure of taking risks and intentionally exposing ourselves to potentially dire consequences provides an opportunity for some to heighten the human experience of being alive. Moreover, it is self-evident that steps into uncharted realms are essential if we aim to evolve as human beings. Ken Wylie’s work in risk management in the outdoor community has given him profound insight into the dynamics of risk and the meaningful impact that such activity can have on our lives. Our actions have the potential to be creative and productive or tragic and destructive. Carl Jung identified that the most hazardous thing for humans is themselves, fuelled by denial of the existence of what he called “shadow.” Shadow is the lack of acknowledgement of our profound capacity for harmful action. Invalidating our potential to make poor choices means we can’t envision any need to raise our game in any way or for any reason. We will see how this awareness has great utility in propelling us through our fragmented state and onward to wholeness, a platform for making wise choices that result in our evolution. Awareness of the simultaneously corrosive and fortifying choices we can make is the second gift. We need to ask ourselves, while in the midst of any adventure or challenge, whether we are progressing from denial to acceptance of responsibility, traversing from faintheartedness to courage, coming through isolation into connection with others and ourselves, passing from hubris to grace or inspired action, from deception to truth, from intellectualizing to using our intuition and chaos to embody peace. This is the archetypical human journey of acknowledging and capturing the energy of our flaws to propel ourselves toward wholeness.