The Art of Unconventional Warfare

: A Timeless Doctrine for a Shifting World

Ever felt like you're playing by rules no one else respects? What if I told you the true power lies in ditching the rulebook altogether?

We're living in a world that never stops spinning, and frankly, if you’re not moving with it, you’re getting left behind. This isn't just about the battlefield anymore; it's about the boardroom, the political arena, and even your social life. The principles of unconventional warfare, as laid down by the ancients and refined through millennia of blood and guts, are more relevant now than ever. Forget your grand theories and predictable manoeuvres; it's time to get a bit dirty, a bit unexpected.

The Serpent’s Kiss: Why the Unconventional Bites Harder

Human nature, eh? We crave order, predictability. We build walls, both physical and mental, to keep the chaos out. That’s why the unconventional hits us where it hurts. When someone – or something – defies those ingrained patterns, it sends a ripple of disturbance, a genuine WTF moment. And in that moment of mental disarray, that’s when their guard drops, and they become vulnerable.

Think about it. You expect a punch from the front, don’t you? You brace for it. But what if it comes from the side, or from behind, or when you’re busy tying your shoelaces? That’s the essence of it. The shock isn't just physical; it's deeply psychological. Julius Caesar, a man who knew a thing or two about unsettling the enemy, summed it up perfectly: "No one is so brave that he is not disturbed by something unexpected."

The problem, as ever, is that what’s unconventional today becomes conventional tomorrow. The enemy adapts, they learn, they even innovate to counter your brilliance. It’s a relentless, brutal cycle. You either innovate or you die. And in our fiercely competitive world, this often means resorting to tactics that would make your grandad blush. Propriety goes out the window when survival’s on the line.

Four Pillars of the Unorthodox Game

So, how do you play this game? The masters, from Sun-tzu to the grunts in the trenches, have, consciously or not, adhered to these four principles:

1. Operate Outside Your Experience

People filter the present through the past. It’s how we make sense of things. But if you can contrive a strategy that falls completely outside their frame of reference, you’ll induce pandemonium. The French in 1940 had heard of the Blitzkrieg, but they hadn't felt it. When the German tanks rolled, it wasn't just a military defeat; it was a psychological collapse.

Your job is to know your enemy better than they know themselves. Understand their biases, their comfortable routines, and their rigid ways of thinking. Then, hit them with something they simply haven't accounted for. Once they’ve experienced it, it’s no longer outside their experience. So, don’t repeat yourself.

2. Unfold the Extraordinary from the Ordinary

This is pure Sun-tzu. You set them up. An ordinary, conventional move. Something utterly predictable. They get comfortable, they think they’ve got you pegged. Then, BAM! You unleash the extraordinary. A stunning blow from an entirely unexpected angle. Picture a magician lulling you with a simple card trick before he makes the elephant disappear. The ordinary provides the context, the foil, against which the extraordinary truly shines.

The trick is, the second time you try that amazing feat, it’s not extraordinary anymore, is it? So, you might even revert to that initial "ordinary" move for your actual main attack, because it's the last thing they’d expect. The ordinary and the extraordinary are a constant, spiralling dance. Like a good surrealist painting, the real shock comes from how the bizarre emerges from the mundane.

3. Act Crazy Like a Fox

We humans are terrified of what we can’t predict. That’s why real irrationality sends shivers down the spine. People acting genuinely unhinged? You give them a wide berth. It’s primal. But there’s a secret power in this. A carefully cultivated unpredictability.

You don’t go full-on barking mad. That’ll get you locked up. But an occasional, strategic flash of the irrational? Just enough to keep everyone guessing. A random, seemingly meaningless decision that throws them completely off balance. It’s a form of psychological therapy, this. A chance to break from the suffocating demands of always being "normal." The terror, the respect, the fear – they’ll all be there. Remember Hamlet’s madness? It was a calculated act. Yours must be too. Real madness, ironically, is utterly predictable in its chaos.

4. Keep the Wheels in Constant Motion

This is about fighting obsolescence, both personal and strategic. You get comfortable, you get old, you get predictable. Look at Napoleon. He started off as a genius of fluid, unconventional manoeuvres. But as he aged, he leaned on the sheer size and might of his army, losing that spark, that taste for the unorthodox. And look how that ended, eh? Waterloo.

You’ve got to fight the psychological ageing process harder than the physical one. Break your own habits. Act counter to your past behaviour. Practice unconventional warfare on your own mind. Keep stirring the grey matter, stop anything from settling and becoming conventional. Because when you’re truly unorthodox, you’re not imitating anyone. You’re fighting to your own rhythm, adapting strategies to your own quirks. And that, my friend, makes you a goddamned enigma. And an infuriating, terrifying one at that.

The Dirty Truth

We’re hardwired for convention. Something works, we latch onto it, and it becomes doctrine. This is particularly dangerous in war, where the stakes are unbelievably high, and the safe, proven path suddenly becomes incredibly appealing. But when you’re on the back foot, when the tide’s against you, that’s precisely when you need to forget the books, throw caution to the wind, and risk everything on the untried.

The unconventional isn't always about grand gestures or dramatic reveals. It's often about those simple, ignored ideas that would utterly upset your opponents. It’s about cutting yourself loose from the past. It’s about the mental process, not just the action itself. Because what truly shocks, what truly lingers, are those ideas that sprout from the mundane, twist into something unexpected, and make us question the very fabric of reality.

So go forth. Be unpredictable. Be the serpent in the garden. Just remember: it’s a tightrope walk. Too much, and you’re just weird. Too little, and you’re just another brick in the wall. Find that sweet spot, and you’ll find yourself with a power you never imagined.

Robert Greene, The 33 Strategies of War.

24: TAKE THE LINE OF LEAST EXPECTATION. THE ORDINARY-EXTRAORDINARY STRATEGY.

Event Portfolio

Street Portfolio

Previous
Previous

Echoes of Giants

Next
Next

The Mind Palace Imperative