An Introduction to Strategy (Reading List)

Strategy: a plan of action or policy designed to achieve a major or overall aim.

Strategic thinking is a sought after skill, but it’s not usually taught in school. It’s somewhat of a hidden art that most people learn by apprenticing under other strategists. But what do you do if you’re curious and want to learn the basics of strategic thinking and you don’t know a strategist? Fortunately for us, strategists have captured their thoughts and lessons learned throughout history in books.

Below is a list of books that I recommend for anyone who is interested in strategic thinking. These are not the only books on strategy I’ve read, but these were especially beneficial at the beginning of my journey.

*Listed in no particular order.

  1. 33 Strategies of War by Robert Greene: 33 Strategies of War combines histories greatest works of strategy into one book. Greene examines the past and explores historical figures like Napoleon, Carl von Clausewitz, Shaka (Zulu), and various others to provide examples for each strategy. Some consider this book to be the contemporary companion to The Art of War. This is easily the most beneficial strategy book I’ve come across.
  2. The Book of 5 Rings by Miyamoto Musashi: Miyamoto Musashi, who many consider the greatest swordsman to have ever lived, highlights the strategy of the individual warrior. His principles can be applied to individuals or groups. You have to really listen and meditate on what Musashi is saying in order to apply it to modern life.
  3. The Infinite Game by Simon Sinek: Many consider Sinek’s latest book to be a work on leadership, but the book really discusses strategy from a leadership point of view. Sinek focuses on two types of games that leaders play; one is finite and the other is infinite. He explains how picking a finite strategy in the infinite game of life, business, politics, etc. can have severe consequences for leaders and those in their charge.
  4. The Art of War by Tsun Szu: The Art of War is widely considered to be the greatest work of strategy in history. The methods contained in the book have been tried and proven again and again since its creation. It’s written about military conflict but its not uncommon to see the book referenced in business and political circles.
  5. The Prince by Niccolo Machiavelli: I originally came across The Prince during one of my International Relations courses. Written as a gift to the Medici family to get back in their favor, the book focuses on human behavior and provides insight into how a “Prince” should “rule”.
  6. The Audacity to Win by David Plouffe: David Plouffe and David Axelrod were the main architects behind the 2008 campaign of Barack Obama. The book explores the grassroots strategy that Plouffe and Axelrod crafted to defeat Hilary Clinton in the primary and eventually landed him in the White House. If you can put political ideology aside, there are some serious lessons to learn here in Grassroots strategy.

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