Act Strategically

Most people don't see the bigger picture—don't be like most people.
A general looks over a map as he plans a strategy
Strategy is a term that generally makes people think of armies clashing on a battlefield, but the reality is that strategy is part of everything we do. If you want to accomplish your goals in a variety of environments (in other words, be intelligent), you need to come up with strategies that you think will get you to those goals quickly and efficiently. It becomes especially important when other people are involved–they have their own goals and strategies for achieving them, and not having any methods for countering their actions puts you at a massive disadvantage.
Computers are not particularly good at strategizing unless the environment is heavily constrained and well-defined. Even with the advent of ML, computers have a very hard time understanding anything that's not rigidly defined. They compute and take action based on very narrow domains that are previously defined by a programmer, and seeing beyond those domains is currently not possible.
You, on the other hand, have a brain, which gives you the ability to see connections and synthesize strategies based on disparate information. You're capable of gathering data that seems unrelated to a problem and then, like Sherlock Holmes having an "aha" moment, putting the puzzle together. The more you develop this skill, the more of an advantage you possess over machines that can't see beyond their narrowly defined domains.
Embedded within strategy are lots of different sub-skills, such as creativity and leadership. I decided to bundle all of these under the single subject of strategy for the sake of simplicity. If you dive into these learning materials, you'll have everything you need to start not only being strategic, but also creative and able to lead other people. Like all the other skills listed in this book, the skill of strategy has a large amount of transfer.

Learning Materials

Read These

Start out with this short, light book, which walks you through the basics of game theory. Game theory is the formal study of strategy and involves quite a bit of math. But don't worry, this book won't go into that kind of detail–it's primarily concerned with explaining the key concepts in plain English.
On the surface, this looks like a book about one guy (John Boyd, creator of the OODA loop concept) and his impact on the American military. The reality is that it's a deep exploration of strategy, history, psychology and sociology that will change the way you think about pretty much everything.
I included both of these books because they're both excellent distillations of strategic thought. Greene's books are always meticulously researched and filled with insight, no matter what the subject matter. You should go with 33 Strategies of War if you only want to read one for the sake of developing your strategic skillset. But I recommend you check them both out.
Learning how to evaluate information and assign probabilities to events is a critical for forming quality strategic plans. Superforecasting is the result of years of research done by Tetlock and his team on the nature of prediction, and it's filled with actionable information you can use to improve your decision making process.
Strategy: A History by Sir Lawrence Freedman
You don't have to read this mammoth book in its entirety to get value out of it, but it is a magnificent volume. The first few chapters on their own are worth the price of admission for anyone who wants to be a better strategic thinker.

Watch These

Robert Greene, the author of several books about strategy (two of which are in the list above), walks through how Benjamin Franklin turned enemies into allies. Coalition-building is a key component of successful strategies and the lessons in this video are worth internalizing.
You don't need to be an expert in game theory (it's a deep, mathematical discipline), but understanding the basic concepts–particularly the idea of dominance–will help you make better decisions.
The Prisoner's Dilemma by This Place
The prisoner's dilemma pops up all over the place, and explains the behavior of both individuals and companies in many situations. Being able to recognize it is of the utmost importance if you want to avoid lose-lose scenarios in life. Plus you can win game shows!
Offensive Strategy by Military History Visualized
This brief video reviews Sun Tzu's thoughts on offense. Even though it's usually better to find other solutions, sometimes you need to fight. Knowing how to fight then becomes a skill that you must develop.

Play This Game

The Evolution of Trust by Nicky Case
This is a fantastic little illustration of how trust works in a strategic/game theoretic context. It's worth 30 minutes of your time to see how different strategies are affected by trust.

How to Take Action

If you want to get better at a skill, you need to practice. Strategy is no different. Use every situation you find yourself in as a testing ground for strategic thought. No matter how small, walk through each possible scenario you face and reframe your thoughts in a strategic mindset.
Here are some ideas for how to do that:
  • Identify prisoner's dilemmas that you see out in the wild. I'm not going to give any of them away, but they're definitely out there.
  • Consider if a decision you're about to make is the dominant strategy or if you can do better.
  • Try to anticipate the reactions of those around you when you're trying to accomplish some goal. For example, think about how a loved one would react to a request of some kind and think about how you'd deal with all of those reactions. What strategies will absolutely not work? Which one strikes you as the dominant strategy?
  • Break down situations into game theoretic models. Consider if you are playing a simultaneous game, a sequential game, a non-cooperative game, etc.
  • If you're working a job, consider the different strategies you could use to get more assignments you want or a raise. How would you maneuver yourself around your coworkers and managers to get what you want?
Make a habit of being strategic, and I guarantee you'll become a better strategist. And the better you are at strategy, the better your odds are for surviving automation.