24 Books To Hone Your Strategic Mind
Strategy isn’t something that’s taught well in school. Hell, most people probably couldn’t tell you the difference between “strategy” and “tactics” (or even know there is a difference.)
By 
Ryan Holiday
Strategy isn’t something that’s taught well in school. Hell, most people probably couldn’t tell you the difference between “strategy” and “tactics” (or even know there is a difference.)
This is unfortunate, because strategy is something that is critically relevant to all of us – not just those with careers in the military. We all have goals, we all have obstacles to those goals and we all live in a world we do not control. Those things combine to create the necessity of strategy.
The better we are at it – the better we are at doing what we want and need to do.
How do I accomplish what I need to accomplish? How do I find my way, deliberately, instead of stumbling around, in a reactionary fashion? Too many of us live our lives in a sort of haze, acting without a plan or guidance. Too many of us make unnecessary mistakes (costly ones at that), because we lack the ability to craft a strategic vision and a plan.
Like I said, this isn’t exactly our fault. No one taught us explicitly how to do things differently. But the good news is that such instruction is out there. Wise thinkers have been writing and teaching strategic expertise for thousands of years. The problem is knowing where to start.
In this list I want to give you some of the best (and most accessible) books, essays and documents about strategy. Used properly they will help you craft your strategic mind. You were born to be a strategist, it’s up to you to become that destiny.
1. History of the Peloponnesian War by Thucydides
This book – of a long forgotten war – really functions as a biography and strategic analysis of some of the greatest minds in the history of war. We have Pericles, Brasidas, Alcibiades and many others.
The anecdotes and the stories in this book are timeless. If you make your way all the way through it, I promise you will not forget it. Because the war was so long, involved so many different countries and was so varied (sea, land, siege, politics), it basically covers every type of situation you can think of.
Think of this book as a textbook. Read it. (But it is dense so if you need some help, try this.)
2 & 3. Rules for Radicals, Reveille for Radicals by Saul Alinsky
Both Hillary Clinton and Barack Obama studied Alinsky extensively as they mapped their individual paths to power. He is the real originator of the concept of community organization.
Alinsky was also a die hard pragmatist, a man who had ideals but also a sense for working with and through the system to get what he needed. In fact, his best examples in these books is actually how to use the system against itself to get what he needed. These two books are classics and woefully underrated. Read them now.
4. The Power Broker: Robert Moses and the Fall of New York by Robert Caro
The is probably the most definitive and comprehensive narrative of power ever written.
It maps the entire career of the city planner Robert Moses. I know that doesn’t seem like a particularly illustrative case study for power and strategy but Robert Moses lived power. He controlled the expansion and the building of civilization’s most advanced and important city–and he did it because he was a strategic genius (and of course, a power addict).
This book will take weeks to read but it will stick with you forever. After you are done, I promise you will not forget or ever underestimate the importance of hidden influence, power and levers again.
4 & 5. The 33 Strategies of War, The 48 Laws of Power by Robert Greene
Of course, I am biased because I trained under Robert. But if I had not, these books still would have given me a priceless education (as they have for millions of other people).
Robert is a crack researcher and storyteller – he has a profound ability to explain timeless truths through story and example. You can read the classics and not always understand the lessons. But if you read Robert’s books, I promise you will leave not just with actionable lessons but an indelible sense of what to do in many trying and confusion situations. Also the extra benefit of reading Robert is that you get mini-bios of strategic geniuses like Napoleon, Edison, Machiavelli, Caesar, Cortez, and others.
6. How To Profit By One’s Enemies by Plutarch
This short essay from Plutarch is about an important strategic (and life) lesson. Our enemies and our obstacles are always teaching us. There is always some lesson or advantage we can derive from them. But we must make ourselves open to this. We must cultivate an attitude that welcomes these lessons rather than fights against them.
7. The Works of BH Liddell Hart
I recommend ALL of Hart’s books, from Strategy to Why Don’t We Learn From History to his excellent biographies of strategic geniuses like William T. Sherman.
Like Greene, Hart has the ability to communicate and explain timeless truths about strategy and power. Reading one of his books is the equivalent of reading many other primary texts because he so expertly synthesizes and communicates what lies within them. He is also eminently quotable–which makes the lessons that much easier to recall. For instance, he reduced Sherman down to a simple line: Attack along the line of least expectation, and tactically along the line of least resistance.
8. Boyd: The Fighter Pilot Who Changed the Art of War by Robert Coram
Boyd was a world class fighter pilot who changed warfare and strategy not just in the air, but on the ground and by sea. His concepts pioneered the modern concept of maneuver warfare (and were used for the First Gulf War). His method of problem solving and problem analysis – known as the OODA Loop – is now used in boardrooms and everywhere else. He also perfected the art of “Getting Things Done” whether that was in war or in the bureaucracy of the Pentagon. You need to know and understand John Boyd.
9. The Book of Five Rings by Musashi
Musashi was a different kind of strategist, which is why his book is so important. Most of us won’t find ourselves leading armies anytime soon. As a swordsman, Musashi fought mostly by himself, for himself. His strategic wisdom, therefore, is mostly internal. It’s about the mindset, the discipline, and the perception necessary to win in life or death situations. He tells you how to outthink and outmove your enemies. He tells you how to fend for yourself. And isn’t that precisely what so many of us need help with everyday?
10. The Prince by Machiavelli
Of course, this is a must read. Machiavelli is one of those figures and writers who is tragically overrated and underrated at the same time. Unfortunately that means that many people who read him miss the point and other people avoid him and miss out altogether. Take Machiavelli slow, and really read him. Also understand the man behind the book–not just as a masterful writer but a man who withstood heinous torture and exile with barely a whimper.
Machiavelli is a glimpse into a time when power was literal and out for public viewing–when he talks about making an example of someone, he doesn’t mean calling them out, he means putting their head on a pike. Don’t let that scare you because we’re not as far from that world as we’d like to think. Deny that at your own peril.
11. The Strategy Paradox: Why Committing to Success Leads to Failure (And What to do About It) by Michael Raynor
I don’t have a lot of modern books on this list, but this is an excellent one.
We tend to wrongly think that strategy is about coming up with a genius plan and then committing to it. In fact, this is often a recipe for disaster, particularly in business.
Though success often requires a total investment in a particular strategy, this is also the recipe for extreme failure. It’s a paradox.
Michael Raynor’s book has important thoughts on this inherent paradox as well as approaches for mitigating and avoiding it.
12. Eleven Rings: The Soul of Success by Phil Jackson
Phil Jackson is a master strategist and leader. You don’t win 13 championships in multiple cities if you’re not.
What’s interesting about Jackson’s approach is how eastern it is–he guides by giving up control, he leads by encouraging other leaders, he favors movement over resistance. He has articulated these concepts in an incredibly accessible way in his most recent book and I strongly suggest everyone read it.
13 & 14. Don’t Think of an Elephant!: Know Your Values and Frame the Debate — The Essential Guide for Progressives by George Lakoff and Words That Work: It’s Not What You Say, It’s What People Hear by Frank Luntz
These two books are the two best books of political thinking and theater from both the left and the right.
Regardless of ideologies, both are experts in influencing and leading public perception through image and words. It actually matters whether we’re talking about illegal immigrants or undocumented workers, or whether we describe the problem as climate change or global warming.
Strategists need to understand the power of language and framing–it doesn’t matter how right you are, if you lose this battle it can be impossible to rally people to your cause. Read both these books.
15. Washington: A Life by Ron Chernow
I just finished this book and, goddamn, Washington’s status as an icon shamefully understates his genius as a strategist.
The man had an impeccable intuition for timing, for gestures, for politics, for the moment to strike, not just on the battlefield but in relationships, in office and in his private life.
We must study Washington not only for his nearly unbelievable military victory over a superior British Army, but also for his strategic vision which quite literally was responsible for many of the most enduring American institutions and practices.
I admit this book is long, but it is so good. It is packed with illustrative examples, analysis and stories. Read it.
16 & 17. The Art of War by Sun-Tzu and On War by Carl Von Clausewitz
I know this will offend many strategy purists, but for most audiences I recommend these two books only with a pretty strong disclaimer.
While both are clearly full of strategic wisdom, they are hard to separate from their respective eras and brands of warfare. As budding strategists in business and in life, most of us are really looking for advice that can help us with our own problems. The reality is that Napoleonic warfare does not exactly have its equivalents in today’s society.
On the other hand, Sun-Tzu is so aphoristic that it’s hard to say what is concrete advice and what is just common sense. But the books are so convincing that you might still end up leaving thinking that they can be easily applied. So, again, check these books out if you’re really interested, but I think some of the other books are much better places to start.
18. Nudge: Improving Decisions About Health, Wealth, and Happiness by Richard B. Thaler & Cass R. Sunstein
This might feel like a weird book to include, but I think it presents another side of strategy that is too often forgotten.
It’s not always about bold actors and strategic thrusts. Sometimes strategy is about subtle influence. Sometimes it is framing and small tweaks that change behavior.
We can have big aims, but get there with little moves. This book has excellent examples of that kind of thinking and how it is changing politics, government and business. My favorite example is about the bumblebee that they started putting on urinals–which drastically reduced the amount of spray and spillage because it changed where men aimed when they peed. It’s not exactly the coolest strategy but it solved a problem. So we can learn from it.
19. Billion Dollar Lessons: What You Can Learn from the Most Inexcusable Business Failures of the Past 25 Years by Paul B. Carroll & Chunka Mui
I am putting this book on here as a cautionary tale for all the supposed business strategists out there. Because it turns out that most (if not all) genius business strategies are totally misguided and lead to catastrophic failure.
Your planned merger, roll up, pivot–it’s probably got glaring strategic flaws in it. Why? Because you’re too caught up in your own vision to see what can go wrong, to see where you’ve been overly optimistic, to accept how little you control.
Pairing this book with some of the books on war is a good idea. It will humble you and keep you conservative–which all good strategists are. “Boldness” should be used sparingly because it’s often actually just stupidity in disguise.
20, 21 & 22. The Big Con: The Story of Confidence Men, Whiz Mob: A Correlation of the Technical Argot of Pickpockets with Their Behavior Pattern by David W. Maurer and The Game: Penetrating the Secret Society of Pickup Artists by Neil Strauss
It probably seems weird to recommend books on pickup artists, pick pockets and con men (nor am I necessarily equating the three groups) but it fits.
Though I would accept that most of what these guys do is tactical rather than strategic–they are still quite excellent at identifying opportunities and weaving such flawless, enveloping plans that the marks often have no idea that anything is actually occurring.
A favorite con example is the one where the con man sets up a fake boxing match that he agrees to “fix” with his mark. Taking the marks money, he then fakes the fake boxing match so that it appears that one boxers kills the other in the ring. He and the mark then flee the scene in opposite direction to avoid the police–the mark thinking he got away with murder, when really he was robbed.
The Game is about seduction, literally, but the other two books are about seduction in their own way as well. These books are all classics and will help you, no matter what you do.
23 & 24. The Memoirs of Ulysses S Grant and Williams T. Sherman (Library of America)
These two men won the Civil War despite numerous obstacles.
In many ways, the war was the South’s to lose–they possessed all the territory they wanted at the beginning of the war, they faced a divided enemy, and all they had to do was wait the North out.
The America we live in today is what it is because of the strategic genius and partnership of the Grant and Sherman. Sherman understood the grand strategy of the war–that it depended on crushing the morale of the Southern cause. Grant understand and held the determination required to muddle through battle after battle (along with the destructive politics).
Sherman’s march through the South was a masterwork of planning and vision. Grant’s slow maneuvering of Lee, meant that Lee (who I think is massively overrated) could do nothing to stop it. These two books, written by the men themselves, are about totally unique and priceless historical documents.
Strategy is a rabbit hole that never ends. I am not saying that my list is conclusion–I know it doesn’t even come close. I am just trying to get you started.
I hope these books help. I hope they begin to bring out the strategist inside you. Because there is one there–and whatever you’re working on it will benefit from cultivating that side of yourself.
Now get reading and then get working. Because every word you read in these books become more valuable the more experience you combine it with. Don’t just read about strategy, live it. 
