24 Books To Hone Your Strategic Mind

Ryan Holiday
Strategy isnt something thats taught well in school. Hell, most people probably couldnt
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 isnt 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, its 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.

2 & 3. Rules for Radicals, Reveille for Radicals by Saul Alinsky

Both Hillary Clinton andBarack 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

of

The is probably the most definitive and comprehensive narrative

power ever written.

It

maps the entire career of the city planner Robert Moses. I know that
doesnt seem like a particularly illustrative case study for power and
strategy but Robert Moses lived power. He controlled the
expansion and the building of civilizations most advanced and
important cityand 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.

The 48 Laws of Power

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 Roberts 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 Ones 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

like W

I recommend ALL of Harts books, from Strategy to Why Dont We

Learn From History to his excellent biographies of strategic geniuses
illiam 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 quotablewhich 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.

Boyd: The Fighter Pilot Who Changed the Art of War

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.

The Book of Five Rings

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 wont find ourselves leading armies anytime soon. As a swordsman, Musashi fought
mostly by himself, for himself. His strategic wisdom, therefore, is mostly internal. Its
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 isnt that precisely what so many of us need help with everyday?

The Prince
10. The Prince by Machiavelli

but a

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 booknot just as a masterful writer
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 doesnt mean calling them out,
he means putting their head on a pike. Dont let that scare you because were not as far
from that world as wed like to think. Deny that at your own peril.

The Strategy Paradox: Why Committing to Success Leads to

Failure (And What to do About It)
11. The Strategy Paradox: Why Committing to Success
Leads to Failure (And What to do About It) by Michael
Raynor
I dont 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. Its a paradox.
Michael Raynors book has important thoughts on this inherent paradox as well as
approaches for mitigating and avoiding it.

Eleven Rings: The Soul of Success

12. Eleven Rings: The Soul of Successby Phil Jackson
Phil Jackson is a master strategist and leader. You dont win 13
championships in multiple cities if youre not.
Whats interesting about Jacksons approach is how eastern it ishe
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.

Dont Think of an Elephant!: Know Your Values and Frame the DebateThe Essential
Guide for Progressives

13 & 14. Dont Think of an Elephant!: Know Your Values

and Frame the Debate The Essential Guide for
Progressives by George Lakoff and Words That Work: Its Not
What You Say, Its 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 were 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 framingit doesnt matter
how right you are, if you lose this battle it can be impossible to rally people to your
cause. Read both these books.

Washington: A Life
15. Washington: A Life by Ron Chernow
I just finished this book and, goddamn, Washingtons 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.

On War
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 todays society.
On the other hand, Sun-Tzu is so aphoristic that its 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 youre really
interested, but I think some of the other books are much better places to start.

Nudge: Improving Decisions About Health, Wealth, and Happiness

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.
Its 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 urinalswhich
drastically reduced the amount of spray and spillage because it changed where men

aimed when they peed. Its not exactly the coolest strategy but it solved a problem. So
we can learn from it.

Billion Dollar Lessons: What You Can Learn from the Most
Inexcusable Business Failures of the Last 25 Years
19. Billion Dollar Lessons: What You Can Learn from the Most Inexcusable
Business Failures of the Past 25 Yearsby 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, pivotits probably got glaring strategic flaws in it. Why?
Because youre too caught up in your own vision to see what can go wrong, to see
where youve 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 conservativewhich all good strategists are. Boldness should be used
sparingly because its often actually just stupidity in disguise.

Whiz Mob: A Correlation of the Technical Argot of Pickpockets with Their Behavior
Pattern

20, 21

It
and

& 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
probably seems weird to recommend books on pickup artists, pick pockets
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 strategicthey 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 policethe 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.

Memoirs of General W.T. Sherman

23

&

24. The Memoirs of Ulysses

Sherman(Library of America)

Grant and Williams

T.

These two men won the Civil War despite numerous obstacles.

In many ways, the war was the Souths to losethey possessed

all the territory they wanted at the beginning of the war, they faced
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

warthat 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).
Shermans march through the South was a masterwork of planning and vision. Grants
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 conclusionI
know it doesnt 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 thereand whatever youre working on it will benefit from
cultivating that side of yourself.