PDF Summary:The 33 Strategies of War, by Robert Greene

Robert Greene asserts that life is a war between you and the forces or entities that seek to control you, hold you back, or destroy you. To be successful—whether in the military, business, or even your personal life—you need to win the war, and to win the war you need a winning strategy.

To help you win your battles, Greene presents strategic insights based on his synthesis of military history, historic writings on strategy, and business dealings. We’ll compare Greene’s recommendations to Geoffrey Moore’s Crossing the Chasm, W. Chan Kim and Renée Mauborgne’s Blue Ocean Strategy, and other strategic advice for competing in the business world and succeeding in life.

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Keep Your Options Open

Greene advises you to keep your options open. The more actions you can take, the harder it is for someone to anticipate what you will do.

As a way to increase the flexibility of your forces, he suggests splitting up your army into small teams that can function autonomously but can also join forces to fight larger battles. Additionally, this increases the number of separate forces that your enemy has to try to keep track of, which compounds the difficulty of predicting your moves or inferring your overall strategy.

Keep Your Options Open in the Battle for Financial Freedom

Greene presents the strategy of splitting your force into autonomous teams in the context of military operations, but you can apply an analogous principle to other parts of life, such as personal finance.

Think of it this way: Your enemy is poverty. Its attacks come in the form of bills, expenses, and other financial setbacks. Your income is the army you use to defeat those attacks, and each of your independent revenue streams is like an autonomous combat team.

If your sole source of income is your day job, this is like having your whole army fighting as one unit: Your options are limited, and if you lose your job, you’ll be at the mercy of your expenses. But if you got an additional part-time job it would increase your options and reduce your risk. If you also invest in stocks, the returns provide another independent source of income. Maybe you also publish a book, create an app, or start a YouTube channel about one of your hobbies. These create additional revenue streams, further increasing your options. Together, these diverse revenue streams create a strong financial army.

Stay Ahead With Bold and Unconventional Maneuvers

When you launch an offensive, Greene recommends that you keep your forces moving fast enough that your enemy doesn’t have time to react. By the time they figure out how to counter your first move, you’ll be well into your second or third, making their response irrelevant.

He also suggests that you occasionally make a move that looks so bold, audacious, or unconventional that it seems almost insane. If your enemies mistakenly assume that you wouldn’t do anything imprudent, they’ll interpret your audacious moves as a sign of greater power than you actually have. Having miscalculated your strength, they won’t be able to predict your moves as easily. If they don’t make that mistake, it will still make you harder to read, because an irrational opponent is, by definition, unpredictable.

Make Your Competitors Irrelevant Before They Catch On

Greene recommends advancing quickly and boldly, even audaciously, to keep ahead of your enemies. Analogous business strategies include blitzscaling, where you grow your company so fast your competitors can’t catch up, and having a blue ocean strategy, where you boldly go where your competitors have never gone.

The premise of blitzscaling is that the key to making certain products successful is to grow your user base as quickly as possible. This works best with digital products that have negligible marginal cost (once you’ve created the product, making additional copies doesn’t cost you anything) and significant network effects (the more people use the product, the more useful it becomes, like social media apps).

Meanwhile, the premise of a blue ocean strategy is to offer a product that provides unique value to your customers. If your product is truly unique, then by definition, there won’t be any direct competition, giving you space to build up a profitable market.

Furthermore, when you introduce a product that’s fundamentally different from the competing products of other industry players, those players initially tend to think you’re crazy and dismiss your product as something nobody would want. By the time they realize that your product has opened up a whole new profitable market, it may be too late for them to compete effectively with you because market leadership tends to be self-perpetuating. (Once your brand has a reputation for being the best in its class, it’s easier to make sales and attract top talent, which helps you continue to make the best products.)

Blitzscaling goes hand in hand with a blue ocean strategy, because it only works in newly opened markets, where you can be the first to secure a majority of the market. When you use a blue ocean strategy, you create a new market where your competitors didn’t see one, which initially confuses them. And if you grow rapidly to dominate the market, the network effect makes your product so much more valuable than any competing alternatives that they’ll never catch up with you, even when they catch on to the new market. This illustrates Greene’s principle that making unprecedented moves and building on them quickly gives you an advantage over your opponents.

Don’t Let Small Size Hold You Back

When you first start out on any conquest, chances are that your enemies will have more resources than you. However, this isn’t necessarily a problem. Greene points out that smaller armies are more mobile and easier to conceal. And if you don’t seem large enough to pose a significant threat, your opponents may simply ignore you.

Greene suggests that you can use this to your advantage by building up your empire from many small conquests. You suddenly take possession of something that, by itself, is not worth your opponents’ time or energy to fight over. Then bide your time, building up your strength and waiting for others to forget about your recent conquest. Once they’ve forgotten about it, you can repeat the process. Greene asserts that over time you can quietly take over a large territory without anyone realizing what you’re up to until it’s too late for them to stop you.

Conquer Niche Markets

In Crossing the Chasm, Geoffrey Moore presents a business application of Greene’s strategy of building up an empire from pieces that, individually, your opponents don’t consider worth fighting for.

Moore’s strategy begins with identifying a niche market for your product. He emphasizes that the first market you target must be small enough for your company to dominate. This is important for two reasons: First, it makes it feasible for you to become the market leader in that niche, which helps you make sales. Second, and more to Greene’s point, if the market is small enough for a startup company to dominate, then it’s not worth enough for larger, established companies to bother fighting over.

Moore advises that, once you’ve established yourself as the market leader in your target niche, you select another niche to expand into. Thus, you build up your market share one niche at a time until you dominate the whole market. In light of Greene’s discussion, part of the reason Moore’s strategy works is that by the time the old market leaders that you’ve displaced realize what’s happening, you’re already too well entrenched in too many market sectors for them to take back much of your market share.

Avoid Pitched Battles

Greene points out that head-to-head battles are costly and often indecisive. Thus, it’s better to avoid them, especially when you’re small and don’t have resources to spare. To gain victory efficiently, Greene advises you to work your way into a situation where your strengths are pitted against your opponent’s weaknesses, and where their strengths and your weaknesses are less relevant.

Greene says that when a large, powerful opponent moves to engage you head-on, your best bet may be a strategic retreat. Not only does this avoid the massive losses of a pitched battle and buy you more time to prepare, but it typically provokes your opponent to chase you, allowing you to lead them to a place where you can fight them on your terms. For this reason, Greene says that the defender in any conflict is statistically more likely to win than the aggressor.

Use Blue Ocean Strategy to Avoid Pitched Battles in the Business World

Blue Ocean Strategy might be interpreted as a business application of Greene’s strategic retreat. As we’ve discussed, with a blue ocean strategy you provide a unique product to create a new, uncontested market. W. Chan Kim and Renée Mauborgne argue that this is more profitable than direct competition because the new market gives your business more room to grow. In Greene’s terms, choosing to market a unique product is like retreating out of your competitors’ territory instead of fighting them head-to-head.

Eventually, your competitors will realize that your product has reshaped the market, but by the time they give chase (in the form of introducing new products to compete directly with yours), they’ll have to fight on your terms because you already have experience in the new market. You’ve developed procedures for producing and marketing the product efficiently, as well as supply networks from which you source your materials. Meanwhile, to adapt to the changing market, your competitors will have to retool, which is slow and costly. In terms of Greene’s strategy, you’ve drawn your competitors away from their familiar territory into terrain where you have the advantage.

Although Kim and Mauborgne don’t refer to their strategy as a retreat, per se, they do emphasize the non-combative nature of their approach. At the time they first published Blue Ocean Strategy, this differentiated it sharply from most other business strategy books, which emphasized combative business competition. Viewed as a strategic retreat, it’s actually both combative and non-combative: You avoid combat up-front, but you gain an advantage over your enemies in the long run.

Fight a Guerrilla War

Greene explains that guerilla tactics are ideal for fighting a large, powerful enemy with a small force. Stage small attacks on your opponent’s weak spots and plunder their supplies to supplement your resources. Even though a single guerilla raid won’t hurt your enemy much, the effect of numerous small raids accumulates over time. This wears your enemy down without ever giving them the chance to defeat you in a pitched battle. It also shows them that they can’t push you around with impunity, even if they’ve put you into retreat.

Use Guerrilla Tactics to Conquer Your Habits

As Greene points out, guerilla tactics work because you can stage small raids relatively easily, even with limited resources. However, these tactics aren’t only useful in battle—other authors suggest applying these same principles to kick bad habits and cultivate good habits.

In Tiny Habits, behavioral scientist BJ Fogg argues that the key to cultivating productive or positive habits is to find the “tiny” version of the habit you want to create, something so easy that it doesn’t take much motivation to do it. He bases this on the Fogg behavioral model, which predicts that, given the opportunity to do something, you’ll do it whenever the combination of your motivation and ability (basically how easy it is) exceeds a certain threshold. Fogg observes that since your level of motivation naturally fluctuates and is difficult to control or predict, manipulating your ability to do something changes your behavior more than trying to manipulate your motivation.

Similarly, in Atomic Habits, James Clear argues that if you focus on making small positive changes to your habits, these small changes get compounded over time, and add up to massive improvements.

Combining these two ideas gives you a battle plan for optimizing your habits through a kind of internal guerilla warfare: Even if your arsenal of mental energy is small, you can use it to make small changes to your behavior, and over time these changes will add up to defeat bad habits and replace them with good ones.

Plan a Decisive Victory

Greene discusses a number of strategic concepts to consider when you’re ready to crush an enemy force for good.

Target the Source of Your Enemy’s Power

First, he says you should consider the root of your enemy’s power. What is it that truly enables your enemy to stand in your way? For example, perhaps you’re outgunned, but their high-tech weapons are dependent on a steady stream of supplies, so the root of their strength is their supply lines. Cut off their supply lines, and they won’t be able to fight you effectively anymore.

(Shortform note: Once again, Greene’s strategy of identifying and eliminating the source of your enemy’s power isn’t limited to military applications. Ray Dalio prescribes this same strategy for dealing with problems in organizations and in your personal life. Whenever a problem arises, or something doesn’t go the way you wanted it to, Dalio advises you to ask, “Why?” not just once, but repeatedly, until you get past the symptoms to the source of the problem. Whether the problem is a bad habit, a defective procedure, or something else, conquering the problem at the source is the only sure way of eliminating it.)

Target a Vulnerable Spot

Greene says you should then consider where your enemy is most vulnerable. Hitting them in a vulnerable spot gives you the opportunity to inflict disproportionately high casualties, improving your odds in the conflict even if the vulnerability isn’t the root of their strength (as in the previous tip).

Green explains that in traditional warfare, an army had a well-defined front, but its flank (sides) and rear were more vulnerable. In a typical flanking maneuver, you would send a small portion of your force to attack the enemy head-on, while the rest of your force circled around to attack them from the side or the rear.

With the enemy’s attention focused on the fighting at the front, their sides and rear would be left vulnerable, and it would take time for them to re-orient toward the new threat when your flanking force arrived. This window of vulnerability allowed you to inflict heavy casualties relatively easily. Generalizing this strategy, Greene recommends finding ways to get around your enemy’s frontal defenses.

Exploit Vulnerabilities With Hidden Strength

Richard Rumelt corroborates Greene’s advice on targeting your enemy’s vulnerabilities in Good Strategy Bad Strategy. Moreover, he adds that your enemy’s greatest vulnerabilities are the ones he doesn’t know about. If your enemy has known vulnerabilities, he will likely try to guard them somehow, but if you identify weaknesses that he didn’t know he had, you can exploit them to full effect. And if you can unleash strengths that your enemy doesn’t know you have against weaknesses that he doesn’t know he has, your attack will be maximally devastating.

For example, suppose you’re in the manufacturing business. Your competitor has a large facility devoted to metal casting machinery, which they see as one of their strengths. You find a way to produce the same product more efficiently using a different process, such as sheet metal stamping instead of casting. Now you can undercut your competitor’s prices, and their investment in casting equipment makes it difficult for them to retool for the new production method—what they thought was a strength turned out to be a weakness.

Break Down the Problem and Eliminate One Piece at a Time

According to Greene, one of the most decisive ways to defeat an enemy force is to surround small units of that force, isolating them and crushing them one at a time. By sending a large portion of your army against a small portion of your enemy’s army, you improve your odds of winning.

(Shortform note: This is a crucial element of Geoffrey Moore’s strategy for Crossing the Chasm, or breaking into the mainstream market with an innovative product. Moore observes that mainstream customers tend to buy from market leaders based on their reputation. Thus, he advises you to pick one specific niche and focus all your resources on becoming the undisputed leader in that particular niche. Once you’ve dominated that niche, you pick another niche that you can adapt your product to, and repeat the process until you dominate the entire market.)

Furthermore, Greene argues that when the target group realizes that they are cut off from the rest of their army, anxiety or even panic will set in. A panicked soldier doesn’t fight well, and makes irrational decisions, making it easier for you to defeat them.

However, another piece of Greene’s advice suggests that this strategy has the potential to backfire. In the context of motivating your own troops, Greene explains that situations where retreat or relief is not an option can drive people to fight so desperately that they are almost invincible. Thus, when you isolate an enemy unit by surrounding them, they may panic or see the situation as hopeless, making them easier to defeat—or, they may become more self-reliant and resourceful out of necessity, making them harder to defeat.

Test Anxiety Illustrates the Danger of Isolating an Opponent

Studies of academic testing corroborate the principle that soldiers cut off from help may either panic or rise to the challenge of battle. Educator Barbara Oakley asserts that the physical effects of test anxiety can either increase or decrease your performance, depending on how you process it.

It’s normal to experience symptoms of anxiety like sweaty palms and butterflies in your stomach before an exam. If you tell yourself these symptoms mean that you’re excited to do your best on the test, the hormones that cause them will actually enhance your performance. But if you think the symptoms mean you’re worried about the test, then the same hormones will amplify your worry instead, degrading your performance.

This is likely the same phenomenon that Greene observed in a military context: Soldiers facing overwhelming odds with no way out surely experience more powerful symptoms of anxiety than students facing a test. As with the students, the anxiety may either enhance or degrade the soldiers’ fighting abilities, depending on how they process it.