7 Books for Strategic Thought

by Caitlin Huxley

When planning a political campaign, you have to look at everything from a top-down view, often called a 30,000ft view, or the big picture. Detaching yourself from your first-person viewpoint takes practice. I find books like these are precisely the kind of practice I need to keep my correct orientation. I often suggest them to interns and staff looking to improve their ability to engage in strategic thought.

The benefit of books on grand strategy is the time spent reading them, considering them as metaphors, and interpreting them as advice for our specific circumstances. The more we read, think, and examine our campaigns from that top-down perspective, the more likely it becomes that we will automatically see new developments from that perspective during the campaign when it counts. My advice is to read and interpret these books until a strategic point-of-view is your default setting.

Listed in no particular order:

"Crescit interea Roma Alba ruinis" - Meanwhile Rome grows on the ruins of Alba.
Rome allied with it's neighbors, and secured mutual defense pacts with each. When any of them went to war with another, Rome would side with the defender, and join forces to conquer the attacker. In this way they grew their borders.

Machiavelli's Discourses on Livy covers Rome's growth as a Republic, and gives us tactics for expanding our own political empires.

48 Laws of Power by Robert Greene

Janus is the Roman god with two faces; one looking forward to the future, and the other looking backward to the past.

Robert Greene advises that we do our best to imitate this; planning for the future and learning from the past. His 48 laws are often contradictory, and leave us to decide which best applies to our situation. Read through and no doubt you will find stories resembling situations where you would have fared better in your own life if you had known these laws.  

The Art of War by Sun Tzu

 "Sun Tzu lived in a cave and ate straw" I was once told. While obviously hyperbole, it pretty much sums up the #1 complaint I hear when recommending this book, that it is old and out dated.

Surely, this book requires being read as metaphor more than most on this list. Some parts may seem useless on first read, such as Sun Tzu’s advice to use signal drums and flags on the battlefield. But if you consider this as the more general suggestion to keep in contact with your troops at all times using the most state-of-the-art technology you have available, it becomes significantly more helpful.

Rules for Radicals by Saul Alinsky

Alinsky's 13 rules are told with more than slight overtones of socialism and self-importance.

As much as The Art of War has to be read as metaphor, this book does not. It is clearly stated, with examples of political action. If you're new to politics or organizing START HERE.

This manual has a sequel, which is nowhere near as good, but years later spawned a response from the Bernie Sanders staffers which is at least as good: Rules for Revolutionaries: How Big Organizing Can Change Everything.

The Power Broker: Robert Moses and the Fall of New York by Robert Caro

This book is long, and I mean really long. The audiobook is 60 hours, compared to the 10 of most of the others on this list. However, as you read through the book, many of the initially dull details do end up becoming relevant.

This is the story of how a young idealist became jaded with politics, and turned himself into a political-capital generating machine. He starts looking the other way to corruption, and ends up corrupt himself.

It's a mixture of a cautionary tale and an inspiring one. Worth the read, and maybe even a reread someday. Just make sure you've got the time to allot to it. 

Strategy by B. H. Liddell Hart

Liddell Hart, a celebrated WW2 strategist, wrote a love letter to the "Indirect approach" as he calls it. A continuation of what Sun Tzu wrote about direct and indirect methods in war, the book gives a number of examples of lateral thinking throughout history, from the Peloponnesian War, to Napoleon, to Hitler's Rommel.

A truly inspiring collection of tales on why doing the unexpected, and taking your opponents by surprise is one of the most effective parts of a successful strategy.

On War by Carl von Clausewitz

Only partially completed by the time of his death, this is the defining manual on strategic warfare. It covers how we use military (or in our case political) campaigns as an ends to the means of forcing others to do our will, how advantages stack up on either side impacting the randomness and chance naturally involved, the benefits of a plan with branches, and more.

This is a very short read, but one I go back to year after year. I would say I have learned more from this book than any other on this list.