Speaking as both a skilled chess player (2400+ online blitz) and winning live 2/5 NLHE player, and one who completely agrees with the overall message of this article, I'm surprised that I also disagree with quite a lot of points.
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First, there's a lot of good points that I agree with:
>> "Chess assumes a controlled environment: perfect information, one opponent, predictable outcomes. Life is much messier."
>> "This is the most important lesson from poker: thinking in terms of probabilities rather than outcomes. Many systems are stochastic, not deterministic. You can do everything right and still get crushed by variance."
>> "Table selection might be the most underrated life skill... The hard part about table selection IRL is that choosing easier tables feels like admitting weakness."
>> "Unlike chess where every piece is visible, poker forces you to make decisions with incomplete data. This mirrors basically every important decision you'll ever make... The key is getting comfortable making high-stakes decisions with 70% of the information rather than waiting for 95%. Because by the time you have 95%, the opportunity is gone."
>> Can you maintain process-focused thinking when you're down 50% of your bankroll? When you just got fired? When a relationship implodes? Most people can't. They revenge-trade, rebound-date, panic-accept the next offer that comes along."
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BUT there's also a lot of very weak points that I disagree with:
>> "See, in chess, the "correct" move is correct regardless of outcome. In poker you can play perfectly and still lose, or play like an absolute donkey and stack everyone at the table."
This is pretty confusing tbh. In chess, the "correct" move will lead to the correct outcome. The way computers solve for the best moves is to work backwards from the resulting game states that these moves lead to. It's actually poker where the "correct" move is correct regardless of the outcome, because the element of luck divorces results from decisions. So, I think I get what you're trying to say, but this way of putting it is pretty convoluted.
>> "Here's where life diverges from poker in a beautiful way. In poker, variance is symmetric. You can only win what's in the pot. In life, variance is asymmetric. The right job, right investment, or right relationship can return 1000x. This means you should actually seek more variance in life than in poker, not less."
This is an extremely bold claim presented with essentially no argument. What about the downside risks? In poker you can only lose the chips in front of you- in life you can lose everything. It would be far more accurate to say that the distribution of outcomes in real life has fat tails, and so you should seek variance while limited the downside tails. But this has now become "try to find free optionality", which is pretty obvious concept and not exactly a lesson from poker or chess.
>> "But once you see life as poker, not chess, you realize something. Chess has a correct answer. There's always an objectively best move. Poker doesn't. Poker is about playing your hand optimally given your bankroll, your position, and your read on the table."
I'm not really sure what this is trying to get at. Optimizing an equation with numerous constraints is still finding the objective best move- and that's what poker players try to do. Most of the article is about how to take the lessons from poker to try to make the best choices given imperfect information. A better conclusion would be "chess makes decisions with perfect information- poker doesn't."
>> Side note- the AI image at the start probably shouldn't have the player holding the deck of cards and definitely shouldn't have both numbers on the 9 of clubs facing the same way.
Incredibly thoughtful analysis, I particularly agree with the 2nd point where the downsides of life can be excruciatingly deep.
But the beautiful thing about playing life is that winning/losing is a false dichotomy. Every "shitty" situation can be converted into an advantage with the right attitude and perspective.
As a statistician, I find the poker life analogy misleading.
In poker, the expected value is strictly constrained: every hand played is governed by fixed probabilities, and the game is ultimately zero-sum, one player’s gain is another’s loss.
Life, by contrast, is neither zero-sum nor bound to a closed system. Collaboration, innovation, and compounding effects mean outcomes can be positive-sum, where everyone benefits simultaneously.
It is fascinating to read a solid analysis from someone with deep insights about Poker and Chess, and there is a lot to take away here.
But your framing is very narrow. Both poker and chess are finite games with fixed rules where it is conceivable to deal in probabilities that are within reason to calculate as a player. Winning is precisely defined and enumerated, there is turn taking, the rules are stable, and it is purely zero-sum with the only externalities being relatively trivial (did a player eat/sleep/lose their job or have subconscious behavior that can be exploited).
No matter how many times you play, it is always the same set of cards and the same rules, so you can grind and become better, even at the modestly stochastic parts.
Poker is a perfect example of a stochastic process where randomness creates uncertainty, but mathematical analysis can still guide optimal play. Life, on the other hand, operates at a totally different level, with ontological indeterminacy, not just epistemological.
Life is like a poker game where you may or may not get a turn, the suits change randomly, and midgame the goal shifts from maximizing chips to stopping an arterial hemorrhage. (Metaphorically, of course)
Business people love the idea of poker as life because a. They don’t really understand life, and b. They fail to recognize that capital presents life as a game by dramatically reducing complexity for short periods . For example, it is obvious that anyone smart should go into private equity or AI, but it is entirely possible that those can collapse completely.
Easily one of the most thought provoking articles I’ve come across lately!
Recently when talking to my long time college friend about why the game of life post college is so different from that in or pre college, I gave the argument of having optionality post college.
There are n number of PnCs possible and one thing that college doesn’t teach is having good judgement. We’ve to develop mental frameworks to make those judgement calls.
You’ve gone one layer deep by presenting the framework and analogising it with poker.
You might be aware that John von Neumann, who basically founded modern Computer Science and Game Theory, said exactly this about 100 years ago and poker was a major motivation for his interest in game theory :
"Real life is not like [chess]. Real life consists of bluffing, of little tactics of deception, of asking yourself what is the other man going to think I mean to do. And that is what games are about in my theory.— John von Neumann"
And if you have any passion for poker and want to improve, check out my app that helps teach game theory optimal play, Live Poker Theory, which incidentally is a speedrun applicant :)
try out the preflop trainer on the landing page : https://www.livepokertheory.com/ which teaches you what to play on the first street based on www.livepokertheory.com/charts , there is also a guide to some intermediate terms here https://www.livepokertheory.com/basics . Honestly its not ultra beginner friendly its more about taking players from intermediate->advanced at this point though happy to hear feedback from a beginner's view
I think all the comments about the nits of chess and poker are nuanced but miss the point. OP uses poker vs chess to paint a motivating analogy about life frameworks. Never let the truth get in the way of a good story. Excellent read.
"I've started using this heuristic: once I have enough information to make a decision that's 70% likely to be right, I pull the trigger or fold"
-- 70%?? I don't think anyone can ever put an number on how much information they have to move forward. If you think you know 70%, then you already know that you don't know 30%. Problem is you will never know what or how much you don't know.
There is a lot of talk about "process based thinking" without ever mentioning what it is or how to develop this.
This article is really good, but somehow lacks the real meat. It smells good, but lacks substance. Was this article heavily LLM assisted?
Great read! I immediately thought of Annie Duke's "Thinking in Bets" book, when I saw it recommended at the bottom. Another of her books, "How To Decide", offers a practical step by step approach to reduce biases and improve decision making.
On book recommendations, I would also add "Reflections" by Marcus Aurelius. Stoicism philosophy overlaps nicely with a probability-weighted approach to life (and venture capital!).
Speaking as both a skilled chess player (2400+ online blitz) and winning live 2/5 NLHE player, and one who completely agrees with the overall message of this article, I'm surprised that I also disagree with quite a lot of points.
----------------------------------------
First, there's a lot of good points that I agree with:
>> "Chess assumes a controlled environment: perfect information, one opponent, predictable outcomes. Life is much messier."
>> "This is the most important lesson from poker: thinking in terms of probabilities rather than outcomes. Many systems are stochastic, not deterministic. You can do everything right and still get crushed by variance."
>> "Table selection might be the most underrated life skill... The hard part about table selection IRL is that choosing easier tables feels like admitting weakness."
>> "Unlike chess where every piece is visible, poker forces you to make decisions with incomplete data. This mirrors basically every important decision you'll ever make... The key is getting comfortable making high-stakes decisions with 70% of the information rather than waiting for 95%. Because by the time you have 95%, the opportunity is gone."
>> Can you maintain process-focused thinking when you're down 50% of your bankroll? When you just got fired? When a relationship implodes? Most people can't. They revenge-trade, rebound-date, panic-accept the next offer that comes along."
----------------------------------------
BUT there's also a lot of very weak points that I disagree with:
>> "See, in chess, the "correct" move is correct regardless of outcome. In poker you can play perfectly and still lose, or play like an absolute donkey and stack everyone at the table."
This is pretty confusing tbh. In chess, the "correct" move will lead to the correct outcome. The way computers solve for the best moves is to work backwards from the resulting game states that these moves lead to. It's actually poker where the "correct" move is correct regardless of the outcome, because the element of luck divorces results from decisions. So, I think I get what you're trying to say, but this way of putting it is pretty convoluted.
>> "Here's where life diverges from poker in a beautiful way. In poker, variance is symmetric. You can only win what's in the pot. In life, variance is asymmetric. The right job, right investment, or right relationship can return 1000x. This means you should actually seek more variance in life than in poker, not less."
This is an extremely bold claim presented with essentially no argument. What about the downside risks? In poker you can only lose the chips in front of you- in life you can lose everything. It would be far more accurate to say that the distribution of outcomes in real life has fat tails, and so you should seek variance while limited the downside tails. But this has now become "try to find free optionality", which is pretty obvious concept and not exactly a lesson from poker or chess.
>> "But once you see life as poker, not chess, you realize something. Chess has a correct answer. There's always an objectively best move. Poker doesn't. Poker is about playing your hand optimally given your bankroll, your position, and your read on the table."
I'm not really sure what this is trying to get at. Optimizing an equation with numerous constraints is still finding the objective best move- and that's what poker players try to do. Most of the article is about how to take the lessons from poker to try to make the best choices given imperfect information. A better conclusion would be "chess makes decisions with perfect information- poker doesn't."
>> Side note- the AI image at the start probably shouldn't have the player holding the deck of cards and definitely shouldn't have both numbers on the 9 of clubs facing the same way.
Incredibly thoughtful analysis, I particularly agree with the 2nd point where the downsides of life can be excruciatingly deep.
But the beautiful thing about playing life is that winning/losing is a false dichotomy. Every "shitty" situation can be converted into an advantage with the right attitude and perspective.
As a statistician, I find the poker life analogy misleading.
In poker, the expected value is strictly constrained: every hand played is governed by fixed probabilities, and the game is ultimately zero-sum, one player’s gain is another’s loss.
Life, by contrast, is neither zero-sum nor bound to a closed system. Collaboration, innovation, and compounding effects mean outcomes can be positive-sum, where everyone benefits simultaneously.
It is fascinating to read a solid analysis from someone with deep insights about Poker and Chess, and there is a lot to take away here.
But your framing is very narrow. Both poker and chess are finite games with fixed rules where it is conceivable to deal in probabilities that are within reason to calculate as a player. Winning is precisely defined and enumerated, there is turn taking, the rules are stable, and it is purely zero-sum with the only externalities being relatively trivial (did a player eat/sleep/lose their job or have subconscious behavior that can be exploited).
No matter how many times you play, it is always the same set of cards and the same rules, so you can grind and become better, even at the modestly stochastic parts.
Poker is a perfect example of a stochastic process where randomness creates uncertainty, but mathematical analysis can still guide optimal play. Life, on the other hand, operates at a totally different level, with ontological indeterminacy, not just epistemological.
Life is like a poker game where you may or may not get a turn, the suits change randomly, and midgame the goal shifts from maximizing chips to stopping an arterial hemorrhage. (Metaphorically, of course)
Business people love the idea of poker as life because a. They don’t really understand life, and b. They fail to recognize that capital presents life as a game by dramatically reducing complexity for short periods . For example, it is obvious that anyone smart should go into private equity or AI, but it is entirely possible that those can collapse completely.
Amazing amazing piece. Almost all of us have some takeaways or other. Thanks for writing.
Easily one of the most thought provoking articles I’ve come across lately!
Recently when talking to my long time college friend about why the game of life post college is so different from that in or pre college, I gave the argument of having optionality post college.
There are n number of PnCs possible and one thing that college doesn’t teach is having good judgement. We’ve to develop mental frameworks to make those judgement calls.
You’ve gone one layer deep by presenting the framework and analogising it with poker.
Great stuff!
Great piece.
Incredibly challenging to execute well on a consistent basis.
But also tough for everyone else. Thus increasing the payoff for those who play life as poker.
Facts
You might be aware that John von Neumann, who basically founded modern Computer Science and Game Theory, said exactly this about 100 years ago and poker was a major motivation for his interest in game theory :
"Real life is not like [chess]. Real life consists of bluffing, of little tactics of deception, of asking yourself what is the other man going to think I mean to do. And that is what games are about in my theory.— John von Neumann"
(source: http://poker.srv.ualberta.ca/about ).
And if you have any passion for poker and want to improve, check out my app that helps teach game theory optimal play, Live Poker Theory, which incidentally is a speedrun applicant :)
How do I check out the app? Don’t know how to play poker but want to learn
try out the preflop trainer on the landing page : https://www.livepokertheory.com/ which teaches you what to play on the first street based on www.livepokertheory.com/charts , there is also a guide to some intermediate terms here https://www.livepokertheory.com/basics . Honestly its not ultra beginner friendly its more about taking players from intermediate->advanced at this point though happy to hear feedback from a beginner's view
I think all the comments about the nits of chess and poker are nuanced but miss the point. OP uses poker vs chess to paint a motivating analogy about life frameworks. Never let the truth get in the way of a good story. Excellent read.
"I've started using this heuristic: once I have enough information to make a decision that's 70% likely to be right, I pull the trigger or fold"
-- 70%?? I don't think anyone can ever put an number on how much information they have to move forward. If you think you know 70%, then you already know that you don't know 30%. Problem is you will never know what or how much you don't know.
There is a lot of talk about "process based thinking" without ever mentioning what it is or how to develop this.
This article is really good, but somehow lacks the real meat. It smells good, but lacks substance. Was this article heavily LLM assisted?
Amazing amazing article
Thank you, absolutely love the theory on have a range of expectations. The entire piece, was refreshing and so applicable.
Amazing, loved the analogy. Any book recommendation, discussing something similar.
Best post I have read today. Also, my business might excited you. Shall I send numbers? I would like to raise from someone like you.
Great read! I immediately thought of Annie Duke's "Thinking in Bets" book, when I saw it recommended at the bottom. Another of her books, "How To Decide", offers a practical step by step approach to reduce biases and improve decision making.
On book recommendations, I would also add "Reflections" by Marcus Aurelius. Stoicism philosophy overlaps nicely with a probability-weighted approach to life (and venture capital!).
Thinking in bets is a great read. Thank you for taking the time to write this!