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Master the DARK ART of Machiavellian Strategy to WIN!

Is it wrong to study manipulation? Or is it more dangerous not to? The truth is, the modern world—whether it’s the corporate ladder, competitive relationships, or business negotiations—is a battleground of strategy. And to thrive in that world, you must master Machiavellian strategy.

Now, this doesn’t mean becoming some moustache-twirling villain. It’s about becoming the controlled monster—a phrase made popular by Jordan Peterson—capable of strategic power, but choosing to use it ethically.

What is Machiavellianism?

Machiavellianism is a psychological and philosophical concept rooted in the ideas of Niccolò Machiavelli, a 16th-century Italian political thinker. It describes a mindset focused on strategic manipulation, pragmatism, and power—often prioritising outcomes over morality.

In modern psychology, it’s one of the traits in the Dark Triad, alongside narcissism and psychopathy. People high in Machiavellian traits tend to be:

  • Cunning and calculated
  • Skilled at influence and deception
  • Emotionally detached
  • Focused on personal gain

While often seen as negative, not all Machiavellian traits are harmful. When used ethically, understanding Machiavellianism can help you navigate complex power dynamics, protect yourself from manipulation, and play the game smarter—especially in leadership, business, and negotiation.

Why You Should Learn Machiavellian Strategy

Let’s get real. In your career, business, dating, or even social life, people are already using tactics. Some of them subtle, some not so much. If you’re unprepared, unaware, or just blindly optimistic, you’re setting yourself up to get walked over.

Master Machiavellian strategy not to manipulate, but to defend, compete, and win.

Niccolò Machiavelli’s The Prince—a brutal yet pragmatic guide for rulers—argues that it’s better to be feared than loved if you cannot be both. That same mindset can be applied, in a modern and ethical way, to survive the power dynamics of today’s world.

It’s about playing mental chess. Strategic moves. Calculated thinking. Knowing how to see through the BS and act with clarity.

Controlled Power Is Safer Than Harmless Weakness

Being harmless isn’t virtuous—it’s vulnerable. The concept of becoming a “controlled monster” is far more powerful. Strength without control is chaos, but control without strength is weakness disguised as virtue.

This doesn’t just apply to physical power (though martial arts is a great analogy). It applies to your mind—your ability to negotiate, persuade, analyse people’s intentions, and assert boundaries.

In fact, Robert Greene’s Law 33 from 48 Laws of Power nails it:

“Discover each man’s thumb screw.”
Everyone has a pressure point. Knowing how to identify them can protect you—and sometimes position you to influence outcomes in your favour.

Spot the Tactics, Beat the Game

One of the biggest benefits of diving into Machiavellian thinking is awareness. You’ll start spotting red flags: evasive language, emotional manipulation, backhanded compliments, performative vulnerability.

It’s all around you—especially in the workplace.

From personal experience in the corporate world, I’ve seen highly skilled workers kept in productive roles while less capable, politically savvy middle managers rise through the ranks by mastering the game. If you’re skilled, you must learn to play the game—or better yet, leave it and start your own.

(For more on navigating these traps, check out How Long Should You Stay in a Job? The Tenure Trap and my YouTube breakdown on the same topic.)

Master Machiavellian Strategy — Ethically

Let’s make this clear: I’m not advocating hurting people.

But if someone tries to manipulate you, should you not respond strategically? Learning Machiavellian strategy gives you the tools to push back. To navigate office politics. To negotiate better. To position your business or career advantageously.

Read Oliver James’ Office Politics which you will find in my reading list to learn more!

In fact, you can think of it like learning sales or marketing tactics. Many high-level strategies are functionally the same—persuasion, framing, influence—only difference is intent.

I’ve used these approaches to compete against big corporate firms who try to muscle in with flashy cars and bloated budgets. Sometimes, you’ve got to fight fire with fire—especially when you’re just starting out.

Dating, Business, and Power Dynamics

Manipulation exists in dating too. Whole industries exist teaching social dynamics—some ethical, some not. But the best route? Improve your value, and stay genuine.

That’s the philosophy behind Mark Manson’s Models—a book I believe is probably the best dating guide out there. It aligns with the idea of becoming “the real guy,” not a fake alpha. You start by learning the tools, then grow into authenticity.

Build Your Personal Sovereignty

Ultimately, to master Machiavellian strategy is to reclaim your power. To protect yourself mentally the way you might physically with martial arts. You don’t need to use manipulation—but you need to recognise it, respond to it, and rise above it.

Real personal freedom comes when your choices, values, and actions aren’t easily manipulated. That’s the root of personal sovereignty.

And in a world where manipulation hides in polished campaigns, high-pressure sales calls, and backroom politics—knowledge is your best weapon.


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