Several Moves Ahead

★ Learning to Think Like a Chess Master

Several Moves Ahead

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Today’s newsletter is all about strategic decision-making and the art of thinking ahead. I don’t want to spoil anything, so I’ll skip the preamble and get to it.

Alright, let’s dive in.

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“I don’t believe in psychology. I believe in good moves.” — Bobby Fischer

I started playing chess in second grade. My teacher, Mrs. Courtney, had a chessboard in her room and taught us short lessons throughout the year. Like everything else at that age, it was simultaneously too complex and oversimplified.

As expected, most of my classmates found the game boring. In each game, it was most common to experience some creative rule change or completely ignore the rules altogether. But a small group of us found solace in this quiet, indoor activity, often prioritizing the game over typical outdoor activities like basketball and soccer.

As with any spirited rivalry, I required an arch-nemesis. In this case, it was a female classmate, we’ll call her Amy. Amy played with her family at home and had far more experience with the game than I did. Day after day, Amy beat me, always finding new ways to thwart my moves. It was infuriating and motivating.

The beauty of playing chess at a young age is that your brain is primed to look for patterns, in part because you have yet to build up biased views of the world.

Each time Amy played a move, I tried to capture it and store it for later, hoping to use it against her. The more we played, the more patterns I noticed. With every game, I was forming a new visual understanding of the world, which I could then use in future games.

Amy would consistently make moves that defeated me.

What separated Amy was not that she made better moves, but that she could anticipate my moves and use that to adjust her play. She was doing what all great thinkers do—thinking ahead.

And while I did eventually beat her once or twice, that was not what stuck with me. What stuck with me was the process required to beat her. It wasn’t through superior moves or increased knowledge of the game; it was in the ability to recognize the potential consequences of each move.

In time, I realized this was called second-order thinking—and chess players are incredible at it.

What is Second-Order Thinking?

There’s a ton of information on second-order thinking, so I won’t spend time recapping or rewriting all of it. For the uninitiated, here’s the TLDR version:

The term was originally coined by legendary investor and chairman/co-founder of Oaktree Capital Management, Howard Marks. Marks first introduced the idea in his book “The Most Important Thing,” in which he attempts to honestly assess his own decisions, missteps, and lessons from a career assessing risk.

First-Order Thinking. Marks describes this as “simplistic and superficial,” noting that “just about anyone can do it.” For example, “the outlook for the company is favorable, therefore the stock will go up.”

Second-Order Thinking: Marks notes that second-order thinking is “deeper, complex, and convoluted.”

💭 Takeaway: Second-order Thinking allows us to explore options in the future so that we can reduce risk today.

Second-Order Thinking: An Example

The goal of second-order Thinking is not to remove every objection or potential pitfall. Instead, it is to minimize negative future outcomes.

In chess, each move creates a series of potential moves for the opponent. What may look like the best move at first, could quickly end the game.

For example, the oldest and most common opening move in chess is the King Pawn opening, and is what famous chess master Bobby Fischer called the “best by test” approach. This move is aggressive. It attacks on the first move and immediately claims the center, freeing up the queen and bishop.

If we were to analyze it with second-order thinking, we’d see the following pros and cons of this move:


  • Gains control of the key central squares
  • Engages rapid development
  • Kingside castling


  • Requires planned opening moves
  • Reduces long-term pressure if black defends

The results:

  • Wins 38.4% of the time
  • Draw 31.3% of the time
  • Lose 30.3% of the time

Simply put: this is a strong position. Does it mean you’ll always win? Nope. But we never get such guarantees, unless the game is rigged in our favor. The point is to eliminate some risk, not eliminate it altogether.

Thinking Like a Chess Master

Chess masters don’t just recognize patterns, they learn to analyze and assess the risks of each potential decision. They follow this path:

  1. Capture the problem. Most of us just dive straight into solutioning. But maybe the problem we first encounter isn’t actually the problem we need to solve. The wrong problem leads to the wrong solution. Start by looking for the problem.
  2. Look for patterns. Once you have the problem identified, start listing out the solutions that come to mind. These are your first-order solutions. They’re the patterns your brain immediately recognizes. Try to just get them all out—your brain knows more than you think.
  3. Analyze and assess your options. Alright, this is the fun part. Start looking at each of the first-order solutions, and evaluating what will happen if you take that action. Think like a chess master, “if I move a pawn to e4, they will [x], [y], [z].”
  4. Weigh it out. Whether it’s for work, family, or friends, our decisions have an impact on those around us. Hiring someone may cause you to lose another employee. Skipping dinner with a friend may lead to a conflict. Second-order thinking is not done in a vacuum.
  5. Act. We’re great at believing our ideas are well-formed, but there’s a reason we seek a second opinion when it comes to important decisions like a medical diagnosis: we only see part of the picture. Sharing your decision process with friends, colleagues, and family will help you see if there are any blind spots in your analysis.

The bottom line is that if you want to become a better decision-maker, you need to go beyond tactics and learn how to analyze the impact of your decisions. Learning mental models, frameworks, and heuristics is always a great place to start. But if you don’t augment your knowledge with decision analysis for your future moves, then you’ll find yourself repeating the same patterns and missing the big opportunities.

Speaking of thinking ahead, what’s next?

I have been working on more “tools for thought” products and will be sharing those in the coming weeks, so stay tuned!

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Thanks for reading, and see you next week,

— Kevin K. (@kkirkpatrick)

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