The next hundred years will be pivotal in the human story. In our time we confront truly existential challenges that could well be our undoing. And while we also find new possibilities, often they leave us overwhelmed rather than providing real hope. Faced with these circumstances, we can react by thinking and acting in ways that are really quite crazy. We find denial in the face of dangers that could be cataclysmic, regressive polarization in response to issues of every sort, and a mix of utopian and dystopian beliefs that could easily lead to self-destructive choices. It is not surprising that we now might encounter ever-increasing rates of anxiety, depression, suicide, and addiction. The Creative Systems Theory concept of Transitional Absurdity helps us make sense of what we are witnessing today. It also helps us better understand what our times ask of us and points toward an overarching solution, one that-with sufficient courage and commitment-can take us forward.