I am a former AI leader turned artist-philosopher, currently on a 1000-day journey to trade the “reckful” drive for optimization for a life of radical vitality. In my late fifties, I have moved beyond the building phase of early adulthood — where we rely on control, calculation, and social approval — to embrace the midlife task of becoming my full, authentic self.
From Optimization to openness
In my previous career, I focused on the logic of prediction and metrics. However, my own life experience — through divorce, a series of post-divorce relationships, and deep study of existential thinkers — revealed that reckfulness (anxious, calculated carefulness) often leads to stagnation rather than growth.
I now advocate for a stochastic philosophy of living. This approach shuns the determinism of the “perfect match” or the “optimized career” in favor of:
- Presence over Control: Meeting the moment without a script or a spreadsheet.
- Becoming over Being: Treating the self as a fluid process in perpetual motion rather than a fixed essence.
- Vitality over Security: Choosing the “courage of aliveness” even when it involves the risk of heartbreak or destruction.
The Reckless Project
Through my abstract painting and my writing, I explore how these principles apply to the four domains of midlife: Romance, Relationship, Reinvention, and Abundance. My work is more manifesto than manual: an invitation to meet your unfolding future with wonder and possibility.
Whether I am in my painting studio, studying the dialectics of Hegel, or reflecting on the unlikely connections found in online dating, my goal is to document the transformation that occurs when we finally stop perpetually trying to control life and instead turn to living it fully.