What “Chess, Not Checkers” Means (And When to Say It)

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Learn how to apply the “chess, not checkers” mindset to your life

Co-authored by Cynthia Orduna and Raven Minyard, BA

Last Updated: November 5, 2024 Fact Checked

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"Chess Not Checkers" Meaning

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When to Say "Chess Not Checkers"

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Where did “chess not checkers” come from?

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Applying the "Chess Not Checkers" Mindset

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The phrase “chess, not checkers” is an idiom inspired by the differences between the games of chess and checkers. Because chess is more strategic than checkers, the phrase refers to planning ahead and thinking about your end goals when making important decisions. In this article, we’ll teach you everything you need to know about what the phrase means and when to use it, plus where it came from and how to apply the "chess, not checkers" mindset in your life.

Meaning of "Chess, Not Checkers"

“Playing chess, not checkers” is an expression that means to make strategic decisions rather than impulsive or easy ones. It comes from the idea that the game chess requires more strategy and thought than checkers, which is a relatively simple game. The phrase can be applied to both business and personal decisions.

Section 1 of 4:

What does “chess, not checkers” mean?

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“Chess, not checkers” refers to making strategic decisions. This popular idiom comes from the idea that checkers is a simple, straightforward game, while chess requires much more forethought and strategizing. If you’re playing chess, not checkers regarding business or personal decisions, it means you’re planning ahead and thinking about the endgame rather than short term goals.^{[1]
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- For example, if you choose a job that has great benefits and room for growth over a job that offers a tempting sign-on bonus, you’re playing chess, not checkers by considering how it will benefit you in the long-run.
- Playing checkers requires you to make quick decisions to capture your opponent’s pieces, which means you get results immediately. There are also fewer moves you can make and directions you can go than in chess.
- In chess, pieces move in different directions based on their individual role, and it’s often important to sacrifice pieces in order to win the game. You don’t always get results as quickly as you do with checkers. This highlights the importance of strategic thinking.

Section 2 of 4:

When to Say “Chess, Not Checkers”

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When you’re thinking through business decisions and strategies Many business leaders and entrepreneurs adopt the “chess, not checkers” mindset and believe it is a great way to succeed. Think about your long term goals and what strategies you can use to reach them rather than focusing on what’s directly in front of you. Remember the unique skills that you and your coworkers or employees bring to the table, and use those qualities to your advantage.^{[2]
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- “Each of my employees has unique skills and assets, so I try to assign them tasks that play to their abilities. Running a business is chess, not checkers.”
- “When choosing a job, think about your endgame. What legacy do you want to leave? Don’t choose something just because it’s easy. Play chess, not checkers.”
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When you’re making long-term personal decisions The “chess, not checkers” mindset can be applied to almost any aspect of your life, including relationships, financial decisions, and more. Just like in business, it’s important to think about your long term goals and figure out how to work toward them. Don’t let the little things get in your way.
- “That guy might be flirting with my crush right now, but I’m not worried. He’s playing checkers while I’m playing chess.”
- “Some people don’t understand why I chose community college over a university, but I’m getting an education and saving money. I’m playing chess, not checkers.”
- “I suspect my partner might be cheating, but instead of accusing them, I’m going to let them tell on themselves. Chess, not checkers.”
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When you’re outsmarting others Many people also use this phrase to indicate that they’re smarter than someone or to make fun of someone for not being as strategic as them. When used this way, it’s a way of saying that you’re a step or two ahead of someone in your current situation. It doesn’t necessarily have to be about important decisions, though it can be.
- “Look, you’re new around here. You’re still playing checkers while the rest of us are playing chess. You’ll figure things out eventually.”
- “I always beat my friends at video games because I strategize instead of blindly attacking. They’re playing checkers. I’m playing chess.”

Section 3 of 4:

Where did “chess not checkers” come from?

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The phrase may have originated in the business world. “Chess, not checkers” is a common idiom that has existed for a long time, so it’s hard to pinpoint its exact origins. However, the phrase is extremely common with entrepreneurs and business leaders, with many people using it in inspirational speeches.^{[3]
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- Mark E. Miller even wrote a book titled Chess Not Checkers: Elevate Your Leadership Game.
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It’s often used across pop culture and media. “Chess, not checkers” can apply to many things other than business decisions, however. Many people recognize the quote “This sh*t is chess. It ain’t checkers” from the 2001 Denzel Washington movie Training Day. Others may think of Kobe Bryant describing his opponents: “These young guys are playing checkers. I’m out there playing chess.”^{[4]
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Research source} Over the years, the idiom has become a part of everyday language.
- YouTube personality H3H3 has also used the phrase to mock rival SoFloAntonio, which led to it becoming somewhat of a meme among his fans.

Section 4 of 4:

Applying the "Chess Not Checkers" Mindset

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Whether you’re applying the “chess, not checkers” mindset to your business, relationship, financial, or general life decisions, consider what you’re ultimately working toward. This could be a promotion, marriage, buying a house, etc. While there will be short term goals and distractions along the way, don’t lose sight of your endgame.^{[5]
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Once you’ve established your long term goals, think about what short term goals can help you get there. Break your goals down into actionable steps to help you stay organized. Create a timeline to stay on track, and check in on your plan each time you complete a step. Adjust your action plan as necessary to make sure you’re making the right decisions.^{[6]
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Be proactive, not reactive. Having a proactive mindset is extremely important to achieving your goals. Anticipate problems ahead of time and look for opportunities to overcome them—just like in chess, when it’s important to anticipate your opponent’s moves. Don’t wait for things to happen and react to them after the fact; take initiative to make things better.^{[7]
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- For example, if you’re saving up to buy a house, expect setbacks along the way. Your car could break down or you may get injured, which would require you to spend some of the money you have saved up. Be proactive by having an emergency fund set aside so you don’t have to react by taking money out of your house fund.
In chess, it’s important to know how each piece works and moves so you can make the best decisions. If you jump right in without strategizing, it may cost you the game. Similarly, if you keep running into roadblocks while trying to achieve your goals, stop and think about what’s happening. If you keep facing the same problems over and over, it’s likely an issue with your strategy. Stop and reevaluate your plans before continuing.^{[8]
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Not every decision you make has to involve the “chess, not checkers” mindset. Sometimes, it’s okay to make decisions in the moment.

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