THE BENEFITS OF BROKENNESS
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WAR & BASEBALL: A BLOG

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9/18/2026

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H.P. Lovecraft: "The oldest and strongest emotion of mankind is fear, and the oldest and strongest kind of fear is fear of the unknown."

We tend to think of fear as something loud and visible, but most of the time it works quietly, guiding how we interpret the world. Our greatest fear is that of the Unknown. And it is everywhere. So, what do we do? We tend to favor what’s familiar. We gravitate towards structures that give the impression of control. In short, we manage it by keeping it at a distance. That is, most of us do. But there is another way, and it is one of awareness. It comes with strategically using the unknown as a emancipating force for uncovering antagonisms and living well within them, not pushing them out of sight.
 
I’ve spent many years trying to expose how these concepts are not just personal but also influence the business world. Most of our businesses find themselves pushed around by forces that seem out of their control. They feel in a perpetual fire drill. But our businesses too can become enlightened, with the right level of awareness.
 
Risk and Opportunity (R&O) management is a good example. It exists because, in complex business environments, uncertainty is unavoidable. It is our attempt to face the unknown in a disciplined way. But the same instinct that drives us to create R&O practices—the desire to contain uncertainty— is also what can make those systems unreliable.
 
When R&O activity is segregated from everyday execution and confined to periodic reviews, separate registers, or specialized roles, it creates a subtle but critical distortion. Uncertainty is something to try and uncover but still is treated as something that lives “over there,” apart from the real work. And through this it becomes more an exercise in documentation rather than a continuous part of decision-making.
 
This mirrors how we handle fear in our personal lives; we compartmentalize it. We set it aside so we can keep moving. And while that may offer short-term clarity, it comes at a cost: we lose sensitivity to the signals that matter most.
 
In business execution, the unknown doesn’t arrive as a neatly defined risk. It shows up as friction. As hesitation. As small deviations, weak signals, or things that don’t quite make sense yet. When R&O is separated from execution, these signals are less likely to be recognized for what they are. They remain embedded in the work, managed in disparate daily activity trackers, or worse, unmanaged. The result is a gap between documented understanding and lived reality.
 
The answer, however, is not to simply document and administer to more R&O.
 
Adding more fields, more reviews, or more reporting layers only reinforces the separation. It increases administrative burden without improving awareness. It asks people to step out of the work to describe uncertainty, rather than equipping them to recognize it within the work itself.
A more effective approach is to adjust how we organize day-to-day execution.
 
The work is already generating the signals: decisions made under constraint, shifts in assumptions, delays, workarounds, moments of confusion, unexpected accelerations. These are not just operational details, they are the raw indicators of risk and opportunity in motion. If captured with the right intent, everyday activity becomes the source of truth.
 
Instead of maintaining a separate system for R&O, we can make daily execution data leverageable, structured just enough to surface patterns, In this model, R&O is not an added layer of effort; it is an emergent property of how the work is observed and recorded. This reduces burden while increasing fidelity.
 
It allows organizations to move from static representations of risk to dynamic awareness of conditions as they evolve. It closes the gap between what is documented and what is actually happening. In that sense, R&O management becomes less about maintaining a list and more about cultivating visibility to potentially impactful conditions in a structured way.
 
Just as individuals grow by facing what they do not understand, organizations become more resilient when they stop distancing themselves from the unknown. The goal is not to eliminate uncertainty, that’s impossible, but to remain connected to it as the work unfolds. Because the greatest risk is not the unknown itself, it’s believing it’s being managed somewhere else.
 
I’ve been working on a business book for a few years to organize and further explore the implications of these concepts. If you’re interested in being a pre-reader, please don’t hesitate to reach out.

If you enjoyed this new meditation on the deeper meaning of the game, you’ll love THE ART OF WAR AND BASEBALL!! Check it out here: www.theartofwarandbaseball.com 
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    I will be posting more baseball meditations here over time.

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