Thinking Strategically When the Field Disappears

I’ve owned The Art of War longer than I can remember.

That’s not a boast. It’s an admission. Some books don’t arrive as events. They arrive as companions. They sit on shelves. They move houses. They get replaced when bindings fail. You don’t talk about them much because they’ve already done their work quietly. They become part of how you think without announcing themselves.

I read Sun Tzu early in my career, when everything felt sharper and more absolute. I read it again later, when decisions carried names and consequences. I read it again after that, when experience had stripped away some certainty and replaced it with caution. Each time, the book felt less like instruction and more like a warning. Less about how to win and more about how easily you can lose by misunderstanding what you’re actually doing.

Sun Tzu never cared about battle the way people think he did. He cared about restraint. About clarity. About recognizing when force is a failure of imagination rather than a solution. He wrote for people who had authority, not because authority guaranteed wisdom, but because the absence of wisdom at that level was catastrophic.

That context matters because it shaped how I read The Art of Cyber Conflict when Henry handed it to me.

Henry didn’t present it as something revelatory. He didn’t frame it as a capstone or a manifesto. He handed it to me the way you hand someone a tool you trust, without explanation. I read it then, when it was new, when cyber still carried the faint illusion that it might someday settle into something orderly and contained. I understood what he was trying to do. I respected it. And then I put it on the shelf.

Not because it failed, but because serious books often wait for you to grow into them.

Years later, I pulled it back down.

That reread changed the experience entirely. Not because the book had changed, but because the world had. The language around cyber had grown louder, more confident, and less precise. Everything was a crisis. Everything was escalating. Everything demanded a reaction. We became fluent in tools and strangely illiterate in meaning.

That’s when the structure of Henry’s book became clearer.

This is not a book about cyber in the way the industry uses the word. It’s not about platforms, controls, or threat feeds. It’s about agency, a concept Sun Tzu would have recognized instantly. Who can act. Who can decide. Who can shape conditions rather than respond to them. Henry’s insistence that cyber conflict is primarily cognitive rather than technical isn’t rhetorical. It’s diagnostic.

We like to believe that complexity absolves us of responsibility. That when systems become opaque, outcomes become inevitable. Both Sun Tzu and Henry reject that comfort. They insist that confusion is not neutral. It is created. Maintained. Benefited from. And often chosen because it allows decision-makers to avoid committing themselves.

This is where Henry’s definition of cyber conflict becomes controversial and, in my view, essential.

He draws a deliberate boundary. Cyber conflict exists, he argues, when computational actions meaningfully alter diplomatic or military relationships between entities. That framing excludes most cyber harm. It refuses to label inconvenience, loss, or even significant disruption as conflict unless it crosses a strategic threshold.

In a world addicted to escalation language, that feels almost heretical.

But Sun Tzu would have understood it immediately. Words matter because they commit you to paths. If everything is war, nothing is strategy. If every intrusion is conflict, restraint becomes indistinguishable from weakness. Precision isn’t pedantry. It’s discipline.

The problem, of course, is that the modern cyber environment doesn’t respect neat boundaries. Ransomware groups behave like privateers. Supply-chain compromises achieve strategic effects without uniforms or flags. Influence operations shape civilian perception without firing a shot. The battlefield isn’t just diffuse; it’s plausibly deniable by design.

That tension is real. And the book doesn’t resolve it cleanly.

But Sun Tzu never promised clean resolutions. He warned repeatedly that the most effective strategies are indirect, deniable, and difficult to attribute. The discomfort we feel reading Henry’s definition now is not evidence of its failure. It’s evidence of how far reality has drifted into the gray space both authors warned about.

What endures, on reread, is the emphasis on cognition.

Henry returns again and again to the idea that the most consequential failures in cyber are mental. Misreading intent. Confusing capability with willingness. Believing that visibility equals understanding. Assuming that because something is measured, it is controlled.

These are not cyber errors. They are leadership errors.

Large institutions are particularly vulnerable here. They produce reports the way factories produce parts. Risk travels upward, translated into abstractions, polished until it feels manageable. Agency dissolves. Responsibility diffuses. Decisions wait for a consensus that never quite arrives. Sun Tzu warned that armies fail when command is confused and authority diluted. Henry observes the same pathology in cyber governance.

This is not accidental. It’s structural.

And it’s why this book offers no tactics. No playbooks. No comforting promises. Doctrine isn’t supposed to tell you what to do. It’s supposed to shape how you see before the moment when options collapse, and reaction replaces judgment. That frustrates readers looking for immediate utility. It always has.

I won’t pretend neutrality here. Henry is a friend. I worked for him. That proximity doesn’t soften my view. It sharpens it. I’ve watched how these ideas are tested in rooms where decisions matter, where ambiguity isn’t theoretical, and where the cost of misclassification is borne by real people. Familiarity doesn’t demand praise. It demands honesty.

Reading The Art of Cyber Conflict alongside The Art of War now, after decades of carrying one and years of living with the other, what stands out is not the analogy but the continuity. Both books resist noise. Both distrust certainty. Both place judgment above instrumentation and restraint above reaction.

They are not optimistic works. They are disciplined ones.

Some books want to be quoted. Some want to be taught. Some want to be admired for their cleverness.

These books want something more complex.

They want leaders to slow down, to think before acting, and to recognize that in conflict, especially the kind that hides inside systems we barely understand, the hardest discipline is not responding quickly.

It’s knowing what you’re actually responding to at all.

All images are used for editorial and illustrative purposes only. Author photographs and book cover images are included in connection with critical commentary and discussion under fair use. The exhibition photograph (Asset ID: 2427940637), depicting clay soldiers from a Chinese exhibition at the Móra Ferenc Museum in Szeged, Hungary, is used under an editorial-use license to visually contextualize historical and strategic themes related to The Art of War and modern discussions of conflict.