The 33 Strategies of War

Robert Greene

Rating: 10/10

Best Line #1: Velocity creates a sense of vitality.

Best Line #2: The essence of strategy is not to carry out a brilliant plan that proceeds in steps; it is to put yourself in situations where you have more options than the enemy does.

I made a really big mistake the first time I ran a 5k. I got caught up in the pre-race adrenaline. It was so exciting being part of this thing. And since it was my first time, I watched the crowd around me and mimicked their behavior. Some stretched, some did a little jog, some drank water. I did all three. And when the race started, I did what I always do when I’m amped up: I went fast. All the energy, all the anticipation … I launched at the start, running in big, lunging strides, feeling the rush as I passed the crowd, zooming to the head of the pack with the feeling of victory.

Again, I was new to this. So I modeled my behavior and performance according to others. I ran at other people’s pace. I had no pace. I just wanted to feel it, that rush, at the start.

I was exhausted by the end of the first mile. My legs were rubber. I slowed down, nearly collapsed, recovered, and then suffered a wee bit of humiliation over the next two miles as people passed me by at their steady pace.

It was the real-life rendition of that old tortoise and hare fable. I ground my way to the finish and made decent time. But the experience never left me. It was big proof of the wisdom I had ignored:

Run your race.

Most endeavors are best-performed by doing your best and forgetting the rest. In a race, some runners are fast, some are slow, some warm-up beforehand, others don’t. But you’re not racing against those people. Not even in a track meet. You’re racing against the clock. Against your own limitations. Beat your personal best and the scoreboard will take care of itself.

This is true for a lot of sports. When athletes discuss being in “the zone”, they talk about a trance-like experience that somehow leads them into a completely detached point of view. When they’re “in the zone”, these athletes see nothing but themselves, the goal, and the next two or three steps that they will take to bend reality to their desire. Opponents seldom, if ever, show up in their view. It’s another version of the flow state and very powerful.

The Need For Competitive Strategy

Nonetheless, there are circumstances where opponents (i.e., other people) should be the central focus of your endeavor. Whether it’s in boxing, presidential elections, price wars in commodity trading, chess, or literal warfare, these instances have you facing an opponent in a winner-take-all game. One of you must defeat the other to win.

In those cases, you can’t just “run your race.” You can’t merely try to “do your best”. If your best isn’t good enough, you lose. And in a winner-take-all game, losing is unacceptable.

I don’t particularly enjoy those games and try to avoid those circumstance wherever I can. Yet, we all face these moments. When we do, our strategies must be deeply predicated on beating the opponent rather than beating your personal threshold. In other words, if you think your best isn’t good enough, don’t play “fair”. Go guerrilla.

It’s a proven method and it’s one of the hundreds that can be found in this week’s book. Altogether, it gives us a deeper, richer understanding of strategy.

Written in 2007, Robert Greene’s The 33 Strategies of War is a deeply entertaining mix of history, philosophy, self-help, and social commentary. Having read all of Greene’s work, this one is his best. They’re all excellent but, again, this is his best work.  

It also appears to also be his least-popular work. I think the title throws people off.

33 Strategies of … War? Yeah, I’m not into that.

Me neither. But, again, it’s not about war, per se. It’s about the competitive circumstances we face where we must do certain things to win against the opposition. So consider this for a second …

Are you chasing any finite resource that other people also want?

Is it a winner-take-all situation where second place does not yield an acceptable prize?   

Are you facing a clear and obvious enemy? Something that can counter your every move?

You may answer “no” to these questions today but you’ll find yourself in this situation at some point, I’m sure. We all do.

And I should say … if you aren’t facing this situation in some aspect of life today, it might be worthwhile to go find it. Monday’s post about picking an enemy reminded me how invigorating the struggle can be. But pick a good one. After all, iron sharpens iron. A great opponent of some kind can be lead to something healthy. If the fight is done right.

Picking a healthy fight is like a forester conducting a prescribed burn. It builds clears the weeds and builds resilience.

I should emphasize the idea of a “healthy” fight. This isn’t about becoming combative and intimidating. Don’t be a bully. But find something that is big, ugly, and reactive, and employ the wisdom Greene offers us. It might help to read these posts, too:

Monday: It’s Okay. Choose An Enemy.

Tuesday: Fight The Past. Better Yet, Ignore It.

Wednesday: The Self-Authored Strategy.

Thursday: How To Burn The Boats Properly.

There are far more strategies than I can cover in this review so I’m going to highlight three that resonate with me at this time. Two months from now, when I return to this book, I’ll find a whole other set of strategies that fit at that moment. Such is the delightful utility of this book. Of the 33 strategies, you’ll find four or five that really fit at any moment.

The Weakness Of The Crowds

In the fifth strategy, Greene attacks the willowy, ultra-sensitive, workshop-driven method of groupthink that infects a lot of our work today. He writes the following:

The group has a mind of its own, and that mind is cautious, slow to decide, unimaginative, and sometimes downright irrational.

So true! There is wisdom in the crowds and there is weakness in the crowds. Where is the dividing line?

Greene combs through history to find specific situations where inclusive groupthink failed and a command-and-control method succeeded. I think the common pattern, based on Greene’s work and my own research, goes something like this:

Groupthink is best for non-urgent decisions with no specific, desired outcome predefined. In other words, if you don’t have a target to hit, and don’t have a hard time constraint, then go with the groupthink. Build a process … explore … discuss … vote. You’ll eventually make decisions that are, at minimum, lacking any perceived weakness.

These decisions will also lack any strength. There will be no firm identity to those final approaches. The work will be a mish-mash of different values and ideas. Kind of like the worst product designs out there, weighed down with feature bloat and generic marketing.

It’s statistics of a certain kind. Poking at the darkness. Goading a response from the market, the opponent, the test case, etc., so that you can build the next iteration.  

Command and control is best for urgent decisions where specific goals already defined. I won’t get to deep into this but, suffice to say, this is the stuff of startups and calculus as I’ve written about before. More importantly, this is about forging your identity with your work, your authority, and your desire to hold true to a clear style.

For more, I highly recommend the outstanding website Work With Source. If you want to know why some companies and ventures succeed and others fail, start here.  Think about the concept of the gestalt.

For decisions that embrace trade-offs and carry a strength, embrace trade-offs, and accept a weakness, you need to take this approach. Coincidentally, this is the only way forward in competitive landscapes.

Hit Them Back. Intelligently.

Strategy #9 is one of my favorites: the counterattack strategy. It is at the heart of any competitive effort and a fascinating aspect of any fight that we examine after the fact. This is the hinge within the cause-and-effect of all stories we tell ourselves. There seems to always come a point where “the tables are turned”. But what make a great counterattack? It starts with mindset:

A key principle of the counterattack is never to see a situation as hopeless. No matter how strong your enemies seem, they have vulnerabilities you can prey upon.

This is the common thread in every counterattack story I can remember. In the context of war, this story emerges when the defenders have withstood the initial attack from an invading force. When the smoke clears and they find themselves still standing, the defenders discover many things about the situation:

First, they find that the attacker wasn’t as powerful as they thought.

Second, they find out exactly what the attacker’s strength looks like.

Third, they find a way to counter that strength.

Whether it’s the hit-and-run tactics of the NVA or the calculated retreats of Napoleon’s army, the counterattack is predicated on information gathered from the opponent’s initial assault and a creative response around it. In every instance, this creative thinking requires a calm, optimistic mind. There is a certain kernel of hope embedded in the action. We can do this. Here’s how.

I think that’s why finding a competition of some kind is so important to our growth. Nevermind the winning and losing. The test itself forces you to be creative. Necessity is the mother of invention. And in a winner-take-all battle, the great competitors get inventive.

Speed and Suddenness

If the counterattack is a proven strategy for a defender, the blitzkrieg is the proven strategy for the attacker. Strategy #14 is all about the effort to make your first attack the only one you need. Greene writes some really great lines to this point:

Velocity creates a sense of vitality.

You must be slow in deliberation and swift in execution.

Acting with speed and decisiveness will garner you respect, awe, and irresistible momentum.

It’s easy to think that we operate in a world where the idea of a blitzkrieg is neither warranted nor relevant. This easy, understandable idea is also deeply limiting. There is always an opportunity, and a need, to act swiftly, forcefully, every single day. In some regard.

The former Navy Seal turned consultant/podcaster/author Jocko Willink has an expression for this: default aggressive. I like that. It conveys the notion that every action is a miniature blitzkrieg, done with maximum intensity and force and speed.

It’s very Type A, isn’t it? Yes, but Type A isn’t a personality. It’s a deliberate strategy anyone can adopt for a given situation. And despite my admiration for Mr. Willink, I don’t recommend the Type A Blitzkrieg approach for everything.

But if you don’t have this default aggressive mindset for something (not everything, but something) then I’m not sure what you hope to accomplish. You’re not sure either. In competitive circumstances, this feels like the most important strategy of them all.

Strategy Books So Far

With this review, I’ve now covered three books written on the formal topic of strategy. It started with the best book on strategy, Richard Rumelt’s Good Strategy, Bad Strategy. The review can be found here. That books lays the foundation for how all strategy must be developed. It is the trusty hammer of any good strategic thinker’s toolbox. Better yet, Rumelt’s work is a fantastic framework for problem-solving in general.

Next came a focus on business strategy. The best book for that is Lafley and Martin’s Playing To Win. Here’s a link to that review. This book illustrates how great strategy, in the business world, is a true manifestation of “running your race”. Find your strengths, find your customer’s needs, and blend the two in a product or service that will “win” by delivering value to the customer.

This marks the third book. And again, this one is focused wholly on competition. I needed to read this again to remind myself that competition is a beautiful thing. We can’t avoid it. Nor should we. Cultivate it where it serves you and you’ll unlock one of the most tried-and-true methods of growth.

I’ll review two more books on strategy before we reach the end of this broader project. The first, titled Blue Ocean Strategy, will argue persuasively for the instances where competition is a bad thing. This idea rhymes deeply with what we’ll find in Peter Thiel’s work, Zero To One. Both books will be featured in coming months and that will round out my review of the best literature on the topic.

Do you need the wisdom of all five books to truly understand strategy? I think so. It’s a deep, difficult topic and so many people trip up because they’ve never read anything on the idea. That said, do you need all five books in order to be successful? No. Of course not. Many people stumble into winning strategies without ever realizing it. As the saying goes, a blind squirrel still finds an acorn or two. But thousands of you have come along this far, dear readers, because I think you see the value in seeing.


Make no mistake: this book is potent. It is a recipe book for strategy but it also a playbook for manipulation. I once wrote that we’re all being manipulated. All the time. Everything is manipulation.

I still believe that. So this is a book that helps us manipulate properly when the stakes are the highest. Greene does well to leaven the ideas with a firm sense of morality. All the same, anyone who reads this book, and only this book, could use it to become a proto-Machiavelli. So let’s make sure we do this right. Our author wouldn’t want it any other way.

A Final Note On The Beauty Of The Page

This marks the second time that I’ve featured a book by Robert Greene. The first occasion featured his book Mastery. The review can be found here. After a couple samples, I’m fully entranced by Greene’s unique voice. The content is rich and expressive. But that’s just half the fun of his books. Let’s take a moment to admire the books themselves. Greene’s books, in physical form, are some of the most beautiful pieces of work you’ll find.

Have you ever just looked at a printed page? From a newspaper or a technical document? If so, you’ll notice information is displayed in specific, sometimes deliberate, sometimes useful fashions. There can be a real art to document design.

Greene’s books explore that art to the fullest. Open up The 33 Strategies of War and you’ll find information is color-coded, organized in clean sections, full of margin notes, distinct typography, and composed in a format that is consistent but varied. It feels so rich.

They’re worth a purchase if only to look at them. Don’t bother reading the words. The organization of information is impressive in its own right. Here’s the link to the paperback.