
Chess champion Jennifer Shahade tells us how we can borrow from the best chess players' decision-tree approach to avoid considering every possible option and instead "think sideways" to consider the best choices on the board.
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David McRaney
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Middle of the Show.
David McRaney
Welcome to the you are not so smart podcast, episode 340.
Jennifer Shahade
When people think about chess players, they think that we think really far ahead and that we analyze 10, 20 moves deep, which is really rare.
David McRaney
That is the voice of Jennifer Shahade, one of the friends of the show and one of the friends of David McRaney, who is me, your host. And Jennifer Shahade is a three time United States Chess Champion. She is an officially recognized woman grandmaster, a Grandmaster of chess. She's also a chess Olympic medalist and Shahadi was the first woman to win the US Junior Open. She plays lots of chess and wins lots of tournaments. And the same is true of poker. She has won poker tournaments in Prague and London and Las Vegas. In fact, she's a two time Global Poker Award winner and she also won writes books about this stuff, especially about how to apply chess thinking to life thinking. She's been on this show before. Back in episode 237 she told us all about her book Chess Queens, which is about the greatest women to play the game of all time. In this episode we are going to discuss her new book, Thinking Sideways, a book that's not really about lateral thinking, it's about thinking sideways. It's very relevant to my current line of research into creative thinking and problem solving as it relates to our folk concept of genius. I'm writing a book about all that and one of the things that I'm obsessed with is something that Shahade is also obsessed with and that she writes about in her new book. And so I thought this would be a great chance to interview her, make an episode about it, promote her book, all those sorts of things. The thing that I'm obsessed with is decision trees. More specifically, there's this myth. It's a common misconception that amazing poker players and other people who do sort of this kind of thing, but poker players specifically, there's a myth that people who get labeled as geniuses within that domain as genius poker players, that they think dozens of moves ahead, hundreds of moves ahead, thousands of moves ahead, and that they see the world that way, that they imagine thousands of possible futures in a this will lead to that and then that will lead to this. And then therefore, if I do this and that and this and that, hundreds of steps like that down the line, they think this way. So they can do something now that will guarantee a desired outcome or avoid an undesired outcome. It's a cool idea. And you may have seen this portrayed in movies and TV shows. Supposed geniuses will often be depicted as if they are thinking hundreds of causes and effects ahead.
Jennifer Shahade
Hey, what was that?
David McRaney
Forward in time to view alternate futures. And that they see all these branching potential futures in a doctor Strange multiverse kind of way. How many did you see? 14 million 605. How many we win? One. And so they choose their actions based on that kind of superhuman foresight. It's certainly cool to think that an incredibly powerful brain could do this. It's just not something brains can do, no matter how dense their gray and or white matter may be. According to the science, according to the evidence on issues such as this, it's just not something that brains are capable of doing. Even a genius, should such a person exist, which is highly debatable and mostly a myth, even that sort of demigod version of intelligence and foresight would not be able to produce this kind of forward thinking, this kind of predictive analysis of future states of the universe. It's just not doable by brain stuff. And you'll learn about that in this interview, and you'll learn what master chess players actually do, which is they think, as Shahade puts it, sideways. You use your experience with chess, your priors, all of the practice you put into it, all that time you've spent playing and identify on the current board the three or four moves available to you right now. And then you rank those moves by imagining what your opponent will do in response. Then you pick the best one of those three or four moves, and if two of them are equally good, you just pick one of those at random and you just make the move and then you repeat that again when it's your turn. That's not to say you don't think ahead a little bit when ranking those moves in that moment, but you limit that to maybe two, three moves ahead at the most. But even masters of the game rarely do that much work most of the time, as Shahade will explain, they think sideways. They think in terms of the moves available right now and how they compare right now to each other right now. This, as you can imagine, is applicable
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to lots of other kinds of decision
David McRaney
making, whether that be in your profession, your job opportunities, your relationships, your education, and so on. And that is what Jennifer Shahadi writes about in her new book, Thinking Sideways. And what follows is our discussion about that book and a few other side tangents as we nerd out over the collider effect and the Einstelung effect and decision trees and chessboxing and psychological studies into IQ versus hours of practice and more. And so here it is, my conversation with Jennifer Schehader.
Jennifer Shahade
All right, I'm Jennifer Shahadi and I am a chess champion poker player and author of the new book Thinking Sideways.
David McRaney
And you also sometimes punch people in chess related ways. Am I wrong about that?
Jennifer Shahade
Oh, yeah, that's right. I recently played in my first chess boxing exhibitions where I alternated between punching and playing chess. You know, this is a sport I have long admired and I didn't really imagine getting into the ring myself, but I have to say, I love the combination of mental and physical fitness. It feels so complete.
David McRaney
It's so weird. Like, chess boxing is the perfect. Like, let's just. I did not know this existed until I saw your updates about this. I was like, chess boxing, of course, of course. Why not? Like, I can see a poetry competition where we also just like poetry. Judo, we could do that. So for anyone who's never heard of this, which is going to be almost if, if they're like me, lots of people like, what do you do in chess boxing? Is it, is it legitimately you just move a piece and then you get in the ring for a minute? I mean, how does it organize?
Jennifer Shahade
Well, the first ever chess boxing match happened 25 years ago in Amsterdam. And it was actually invented by a German artist who was very good at boxing and very good at chess, but not nearly good enough to become the world champion or professional. And his concept was that by combining the two sports and literally you play around a boxing and then you play four moves of chess and then you go back to the ring and then you go back to the chess, that by combining the two, maybe he could become the world champion. And he did. He became the world champion. And so in my book, Thinking Sideways, I use this as a metaphor for the way that all of us should kind of think about our careers. Because if we can't be Magnus Carlsen or Lennox Lewis or, you know, Kobe Bryant, Serena Williams, maybe we can find an intersection like Chess boxing to be the best at whatever we're doing.
David McRaney
I can totally understand this. I, I, I couldn't find we were talking about this before we hit record. Like I, I was like there's no genre for this book idea I've got going here who care. I'll just make up a genre. Whether this is a thing or, or just the Pretty much my entire not have a boss history of my life has been. I, I guess I'll just do this thing where there's no thing for that thing yet. And that's okay, that's fine. The, you don't have to. This is, this is totally covered in your book. Chess boxing is an excellent example of this. What would you say is your version of this?
Jennifer Shahade
Well, I've always been very creative and analytical at the same time and I think that is my chess boxing and that when I'm in a room full of chess and poker players, I'm looking at things from a more artistic angle. But if I'm in a room full of artists, I'm looking at things from a more mathematical, analytical angle. So I feel like I provide extra value in either sphere.
David McRaney
Okay. This is so in line with, with like for people who listen to this, they're used to this happening. I, when I'm working on a book, a lot of the people that I want to talk to, I'm going to ask you about the book because you know how this is when you're working on a book, everything you're doing is the book. So you're, you're, you someone. It's somebody's birthday party and you walk around and go, you know, when you think about it, birthday parties are a lot like there's anything. If you're, you're, you're cooking lasagna and you're like, you know, when you think about it, lasagna is a lot like. And that you'll end up taking a note and it might end up in the book. I knew that your book Thinking Sideways would be somehow related to the work of this psychologist, this cognitive scientist, Robert Weisberg, who sort of helped pioneer research into creative processes. And a lot of what he writes about is like, hey, this whole genius thing is just a hand wavy word to not actually think about what's going on. When a person makes a leap of insight of some kind. And I have this old used copy of some of the early research. You can see the, the, this is, I know you're familiar with this. This is one of the oldest things in psychology. The, the candle problem. You have some, you ask people, you give them a box full of tax, some matches and a candle. And you say your goal is to get this candle to be on the wall burning and free floating on the wall without anybody touching it and let the candle burn. How would you do that? Go. And people approach this problem from a bunch of different perspectives. And a lot of them can't quite figure out what to do, but they ask them to say out loud, like to speak out loud, what are you thinking right now? What are you thinking right now? What are you thinking? Like, work through the problem openly so we can record it and measure what's going on. And the people who eventually actually solve it, they always follow a path that is so similar to what you write about in your book. They this is actual quotes from the research. This is the person talking. They're like, candle has to burn straight. So if I took a nail and put it through the candle, if I take several nails, make like a row, then I can set the candle on that. That's. It's not going to stick out. But if I take the nails out of the box, I could nail the box to the wall, I could put the candle. So what almost always happens is people, they start imagining a couple of different candidates for solutions and then they start noticing that those candidates won't work. And then they switch to the problem is to make the candidate set viable and then they move down the row, they broaden it out and then they center in on and instead of getting stuck on the original goal, they change the goal to this goal midway. And then they almost always arrive if
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they arrive at the solution.
David McRaney
This remind, I thought of this every, all the way through reading the book. I was like, oh yeah, that's thinking sideways stuff. That's what creativity is all about, is adding creativity to analytical thinking. And they, they're trading off one another down the line instead of trying to think, getting stuck in the tunnel of like, I have to get to the goal, like coming up with a solution and then trying to make everything happen, like you have to get burnt out on it. I know I'm going on around, but I just want to know I'm connecting to this very deeply right now because I, oh yeah, this makes total sense to me. So let me not talk for you. Let's start with this. You wrote a whole book about this and you did this. You carved a genre out of the world, which is books that are about chess, but they're not about chess. They're about like things you've learned while doing a lot of chess stuff. And it makes it easier for the reader to make sense of things they wouldn't make sense of otherwise. And I love all your books, and this one's included. This one's called Thinking Sideways. So, Jennifer, as just sort of a rough summary, what is Thinking Sideways?
Jennifer Shahade
Thinking Sideways came out of the realization that when people think about chess players, they think that we think really far ahead and that we analyze 10, 20 moves deep, which is really rare. What we do better, as you describe with this candle problem, is we look at more options and better options. So it's both that our intuition is more refined from playing lots of games, but that we also are good at that initial step of looking at the different possibilities to further check. And that surprises a lot of people because they think of chess players as just being more mathematically inclined, more able to crunch much longer variations into the future and to predict the future, and less about people who are creative about looking sideways, as I like to call it, about the different options. And I think that, to me, this is a beautiful metaphor for people who are successful in life. They're able to discard their plan, be flexible, and be confident that if they see a path that other people aren't picking, it's worth pursuing, and that that part's very tough. I think that it's about confidence and analysis, the confidence to go your own way if you assess that it's the right choice. And, you know, with your work in Changing Minds, I think this is a particularly important one that. That sometimes requires you to do things that are different than what other people are doing. And so you have to be pretty sure that it's worth pursuing.
David McRaney
Yeah, the. Your book, I'm telling you, this is. I. I was like, Jennifer got way out ahead of me already on this because this is. I was like, oh, I'm going to introduce some of this stuff to people. No, you already got there, which is okay, because I know you, and I can just cite you and say, yeah, sure, read this book. But the.
School of Thought / Kitted Thinking Tools Promoter
The.
David McRaney
In the work of the psychologist, the. They talk about analyzing chess players and people who are really. Who have, you know, good track records, exactly what you described, which is like, they bring a lot of experience to the game, but then they don't think 6,000 moves ahead. They think, oh, this is very similar to a situation I've been in before. And I know there are good options and bad options here. Let's take a look at the. And you describe that in detail. I think that's incredible. I. I Think. A lot of people do think this. When you play, you imagine that super amazing chess players are thinking 6,000 moves ahead at every possible. It's the complexity of the, the universe is laid out before them. They, they've seen the movie A Beautiful Mind. They imagine that's happening in their head and it's like they're seeing equations and, and possible futures unfolding. Something from like Doctor Strange World is happening in their head. The. You, you make a point in the book that there are not just billions of possible chess games. The number is, is nutso. How many possible combinations of things could be happening after just the first couple of moves? Yeah, please tell me a little bit more.
Jennifer Shahade
Atoms in the observable universe. It's pretty wild. Of course these are games that are often completely terrible, right? And that's part of the point that the possible games are such a mind blowing number. But great players are very good at winnowing that down and understanding which moves you should actually look at because you would go insane if you look at all of them. But you would also be playing pretty badly if you always pick the first move you see. So it's about balancing, looking at a reasonable amount of moves. A Goldilocks option. I really like to start with people with a number three because I think it's very easy to just tunnel in on one move. And then the next level is you get into binaries and you look at two possibilities. I like people to stretch to three. Sometimes you need to look at four or five. But three is really a good starting point for many people. In fact, when I have students and we're looking at a game, a lot of times I tell them, just give me three options. This is not a test where you have to find the best move. This is a test where you just have to give me three options. Of course that's hard for people because they don't want to give me bad moves. Right. They're used to like having a teacher ask them for correct answers. And here, of course there's probably going to be some answers that are bad, but I want you to give me three. That's the game.
David McRaney
You start out talking about how there's just 20. There are only 20 options at first, but there's 20 options like as your first move. But super chess players like yourself, you don't go, which of these 20, like there's three or four. They are kind of like your favorites, three or four that you're like, I have a move. I have a skill set that follows from these four Am I right? Am I right about that?
Jennifer Shahade
Yeah. There's about four moves that are considered to be the strongest possible first moves, and great test players will choose between them. Now, occasionally, as a surprise weapon, some players will choose like the fifth or sixth or seventh best move. They're not like, terrible, but in general, it's like those top four that we're picking from.
David McRaney
And we can imagine anybody who's fascinated by complexity, science or chaos stuff is like, once the butterfly effect of even chess begins to kick in after just
School of Thought / Kitted Thinking Tools Promoter
a couple moves where you have, oh,
David McRaney
boy, there's a billion possible ways this
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could go from here.
David McRaney
If we were to imagine a supercomputer person, brain expert, genius level, super thing, trying to imagine moves that you were going to do a zillion, you know, moves in the future, it's impossible. Brains are not set up to do this sort of thing. Yeah, but you can. We've all experienced this where we get stuck on a goal that we know will take about seven or eight. I'm talking about life goals. Like, we get stuck on an idea that we want to accomplish five or six moves ahead. And every step forward in this procession is introducing thousands and thousands and thousands of possible things that might happen that are going to affect whether or not you're going to make another decision. I always try to. My thing for this is like the person who orders the second drink is not the person who ordered the first. Like the decision maker who decided to drink the first drink is not the decision maker who's had that first drink. And moving forward from that, this is going to be true for most life situations. You do a great job of, like, helping us understand all this in steps, building a foundation and you sort of separate. Even though we can agree that there are many nuances and variations of human problem solving and planning, we can sort of take it down into two buckets, is what you do. In the book. You've got sort of the scanners versus the tunnelers. If you could help me understand this. What's a scanner do versus what does a tunneler do in situations like this?
Jennifer Shahade
Well, this gets into two common issues. When people look at a chest position or look at a life position. So a scanner will look at all their options. But sometimes they take this too far and they continually scan. You see this for sure in dating and all sorts of scenarios with buying things, making big life decisions that people just want to, to continue to information gather so they'll scan, scan, scan, and sometimes they scan so long that the decision is made for them. They can't choose as many options as before in chess. They would literally lose on time. And then the other person is a tunneler who sees the move that they want and they just play it without looking at their options. And. Well, obviously, as in many cases in life, the beautiful thing to do is to find a option which is in the middle, to scan intelligently and to try to find a move that both satisfies looking at a reasonable number of options, but also not spending so much time on your search that you're wasting time for future decisions. And there's some mathematical puzzles that reckon with this idea of. Famously, the secretary problem is this idea that if you have a number of applicants for a job and you have to decide on the spot who to hire and who to neglect and let walk out the door. So it's a bit of an artificial stipulation. You have 100 potential candidates, and each time you interview someone, you have to immediately let them go or hire them. The math shows you that the best way to tackle this problem is the 36%, where you interview 36% of the possible applicants, and then at that point you pick anyone better than who you've seen in the first 36%. Did I get that right? One second. I think it's 36. Right? 37. Yeah. Sorry, let me do that again. Why did I think. I don't know what.
School of Thought / Kitted Thinking Tools Promoter
Leave it there.
David McRaney
That's fine. You looked it up.
School of Thought / Kitted Thinking Tools Promoter
This is good.
David McRaney
Yeah, this is this.
Jennifer Shahade
I had it in my head that it was 36 or 37 and I picked the wrong one.
David McRaney
No, that's good. I think. I think we're within 1%.
Jennifer Shahade
Yeah, I know, right? It's pretty good. It's pretty good.
David McRaney
That's fine. So if I'm getting this. If I'm seeing this right, like, I'm imagining it, like. And you can see, like, when I was. I was trying my best to map this out so I could ask you good questions. I've got this, like, drawn out where I'm, like, trying to see it as decision trees. Your. Your trees go up, mine go down. I don't know why that is, but the. And I typically say that when I write about things, like, some.
Jennifer Shahade
Because it's. Mine's a tree, Yours is. Mine's a tree, yours is like something else.
David McRaney
Yes. Like some people will say, like, metaphorically or speaking, like. Like the. I'm trying to get a bird's eye view. And some people are trying to, like. I'm trying to dive deeper. I'm trying to look, either way, I get what's like. For some reason, I'm the let's go down to the bottom person. But the I'm seeing it like the person who's tunneling. And you should describe it like this, where, like, let's imagine the goal I'm trying to reach, and it's going to take 10 steps to get there. Trying to, like, sort out, okay, I got to this and that and this and that and this and that. Versus. I'm thinking of it more of, like, an array of possibilities in front of you right here on the board as it sits. Here's what I have in front of me. Label your candidates and then imagine three. And limiting yourself to three helps keep this from the cognitive load from being insane. Beyond that is the veil of chaos. Like, beyond that, there's too many possibilities to even consider, and you're gonna go nuts if you attempt to go that far out. Am I kind of getting that? That's sort of the scanner view of things. Am I seeing that correctly?
Jennifer Shahade
Oh, yeah, right. Absolutely. But that. That's the thing. That's where it gets exponentially vast so quickly, because I might look at three different moves. Doesn't sound like that many. But then I have to look at my opponent's move, and what if I have to look at three of their moves and then another two moves against each of their moves? And now you're starting to see how vast and difficult it is to really parse all of this. And that's actually a lot like life. It is chaotic, and it's very difficult to plan because there are so many things that aren't about you, and they're about other people or they're about luck. So you can only control so much. That doesn't mean you should throw up your hands and not try to make good decisions that, like, what will be, will be. But it does mean that thinking about more options tends to be a spot where you have more control. Once you start going into the future, you lose even more control. And that is why great chess players really need to think sideways even more than they need to think far ahead. Because if I think five moves ahead, but my opponent plays a different move on move 3, then the moves 4 and 5 will have been a waste anyway. It's not going to happen. And that sometimes strikes me when people have really good jobs, really good setups, stable family life, everything is nice. Sometimes I meet up with these people, and they always find something to worry about. But it's often, like, way down the line, like One typical example would be they have a toddler and they're worried about what high school the toddler will go to. And, yeah, I mean, sure, that might be a problem in 12 years, but honestly, if that's still the problem that you have in 12 years, it probably means that things will have gone pretty well for you because more likely there's going to be some other wrench that's thrown in that changes the variables enough that maybe you're not thinking about the question in the same way anyway. So why not just order another drink and think about something else?
David McRaney
Now, I, Yes, I have experienced that just in the last two years. You've experienced weird stuff. Every one of us can go like, hey, what weird things happened to you in the last two, three years that you absolutely had no idea was about to happen? And has deeply affected what's going to happen next. I've had like 11 of those in the last two years. I think we've all experienced that. And it never stops. So. And if I'm hearing you correctly, it's not bad to think, I mean, who. Everybody wants parents who was considering their. The future of their children. It's just your plans are going to get scrambled by. I think, as you write about this, I legitimately wrote this out because there is unpredictable chaos beyond just a few steps in the future, the complexity grows grand. There will be intermezzos. What is that in chess, and how does that relate to what we're talking about?
Jennifer Shahade
Well, an intermezzo in chess is a move where it seems like you're going down a tunnel. It seems like each player has a move that's so obvious you wouldn't even question it. Like, I take your queen. Well, what do you do? You take my queen back. It's the most powerful piece. What else can you do? But once in a while, there's intermezzo. So I take your queen, and somehow you have an unexpected move that allows you to take my queen later and win the game. And these are so difficult to see that even the greatest players in the world will often miss intermezzos. They'll find them against unexpected opponents, and they'll miss them themselves. And I think that it really goes to show that even the greatest thinkers sometimes fall into this habitual tunneling and that being able to work outside of it is so powerful. In life, it often means taking a break from a problem instead of going down the same path. A sudden interruption that gives you more time, that buys you more time, more information. And in chess, they're the way that I've won so many important games. In fact, I'd say they're the most important tactic for any expert level chess player. Because by the time we reach expert or mastery in chess, we already see the kind of basic tactics like the checkmates, the pins, the forks. But they're more like arithmetic, right? Where an intermezzo is like a way of thinking. You can get better at thinking, but you can't just like master thinking. You have to keep doing it, by definition, keep doing it over and over again. So you can't exactly master the intermezzo. You have to continually be, train your mind to be on the lookout and not fixated and not habitually tunneling. And it's difficult because as our intuition gets better, as we get more games under our belt, more years under our belt, we deserve the right to follow our intuition more. You know, we've built up this experience and we're more likely to be right by our intuition. But the problem is just going too far with that concept and then you, you miss out on these life intermezzos.
David McRaney
This, this I, I quote you here.
School of Thought / Kitted Thinking Tools Promoter
It's.
David McRaney
No, this is a paraphrase. It's not about how far ahead you can look. It's about how far sideways you can look. Every chapter of this book brings us back to that idea. But it's, it's such a beautiful thing that they're all going all the way back to the earliest days with behaviorism, like just the very first days of psychology. There they would notice when people enter into a novel situation, they use their predictive processing. There's kind of two paths. They use their predictive processing to see if their priors like, match. And then they try to solve the problem using something they've done earlier in life that seemed kind of similar to that. And after a couple of rounds of that not working, people will tend to just introduce chaos. They will just do some scrambling weirdo stuff to try to create disorder in the system so that it has to jostle something sort of loose from the environment that will then match their predictive processing. It's like this doesn't match the way I expect things to go. Maybe if I like blow it up a little bit and then let the pieces fall where they may. Oh, now I can see a pattern here that I'm familiar with. And in the writing of people like Picasso and others, they've like, that was like their whole life. The way they live their lives. There are no good options in front of me, at least nothing that my Systems are identifying as good options. So what if I scramble things up a little bit and then when I come back to it, oh, there will now be something that seems like a good candidate for moving forward.
Jennifer Shahade
Yeah. Yeah, absolutely. I mean, one of my favorite things about my book is its title, Thinking Sideways. To be rivaled only by my first book's title, Chest Bitch Chess.
David McRaney
You can't get better. You can't get better than that.
Jennifer Shahade
Good names. Good names. Good names. But I feel like the reason you would think that thinking sideways would be a concept that would already be, like, well taken and that it would be not a title that hadn't already been covered. But I think that Sideways actually has a very negative connotation. Like Things Went Sideways is like an idiom for things going wrong. But I believe that that's actually kind of the point.
School of Thought / Kitted Thinking Tools Promoter
Right.
Jennifer Shahade
The fact that people think of it as so bad is partly because we have this fallacy that we have to have it all figured out.
School of Thought / Kitted Thinking Tools Promoter
No.
David McRaney
You write about this. I keep looking at my notes. I love these parts I call this are the many possible futures collapse State. You write, these are quote. These are real, actual direct quotes, not paraphrases. Beauty is in the paths we don't take. This is something you wrote and put in a book. And I read it. And there's another one, which is living with no regrets means you aren't thinking sideways enough. I take from this, and please correct me if I've got. I'm not seeing this the way you're seeing it is since there is unpredictable chaos beyond just a few steps into the future, there's this wave of chaos, a veil of unknowable complexity, butterfly effects in every direction. That means you can rest easy in thinking sideways. Am I kind of on the right path there?
Jennifer Shahade
Yeah. It's a way to comfort people that they don't have to worry about the fact that looking at options will make them regret. And I think that this is very important for people to realize because it's like if you're playing a chess game and you see a winning line that's very beautiful, but you somehow miss some detail so you don't do it. A lot of people feel so devastated, you know, or in poker, if they almost made this wild play, but then they chickened out and they didn't do it. They feel so much regret. And part of the regret is that they had an idea and they didn't follow through with it. But that's normal. If you have a lot of ideas that's going to Happen.
David McRaney
This is. This is what? The price you must pay for thinking too much. Yes, exactly.
Jennifer Shahade
Keep thinking. It's okay. You're gonna. You're gonna come up with good ideas that you didn't follow through on. And that is exactly the price of thinking.
David McRaney
This segues perfectly into. Here's some practical advice that's in the book. And I love this. I've experienced this a gazillion times, and we've mentioned this a couple times in previous episodes. The. I don't know how to properly pronounce it. We're gonna just call it the Einstelung effect or Einstein effect. However you pronounce it, I'll go with that. This is one of the biggest problems with tunneling. And you mentioned research in your book. I've seen other research in other places that more or less says that the better chess players tunnel less. And one of the things that seems to be true about that is, and this is how you put it, when you. If you see a good move, the first thing you should do is look for a better one at that moment. I love this advice. For anything in your entire life, this comes from you. Jennifer writes. I'm paraphrasing. If you see a good move, look for a better one.
Jennifer Shahade
It's pretty much the best advice I think you can get in Chass. And the reason is that when you have a good position, it often has the properties of a great position. So that's where tunneling goes wrong. You just had a huge success in your career, and suddenly you're getting lots of offers. You take the first offer. No, no, no, no. Like, the reason you're getting good offers is because you have the right conditions that you worked hard for. So now this is when you definitely want to scan right, at least not necessarily taking a huge amount of time, but at least taking the time to look at your options. And I think that in chess, this comes up again and again. And we'll see players take a queen when they just have a checkmate on the board. So common. And in life, I feel that it's really important because, unfortunately, you don't always have good positions. Sometimes you have bad positions, and the good position might only come up a few times in a game. So you really need to take the advantage of it, maximize it. The research shows that we can measure this. When people have a good move, they often just play it right. And so if they have a great move and a good move, they'll play the good move. But if all they have is the great move, Then they will find the great mo. So that's interesting because it shows that. That a good move can actually be the enemy.
David McRaney
Yes. This is directly. This is the effect, like when there's something that's familiar. And as soon as you're in the state of ambiguity and novelty, you're going to immediately attempt to assimilate this and try to sort this out, bring your priors into play and go, okay, okay, let's try to make this familiar. Let's try to find a familiar thing within it. Because I have strategies for that. I have things I've done in the past. I've ab. Tested the world a little bit. And then if you ping one, you're like, okay, yeah, I can go that direction. Right. And then with this. In this chess study, they had, as I read it, they had. They produced this thing. These are people who understand chess. They've played it. They're not novices. There's two sort of strategies in front of them. One is more familiar and one is less familiar. It's a little more novel, but it's the better one. And you'll win faster if you go that way. And people tend to pick the familiar one if those two options are in front of them. But if the researchers take the familiar one away, they identify the other one, the other one becomes obvious.
Jennifer Shahade
Right, Exactly. And I think a lot of people understand that anecdotally, and that's why so many people in times of crisis find great opportunities. Right. Like the cliche that. Well, it's not a cliche, but it's often cited that the Chinese character for crisis has opportunity in it. And I think that while that's fantastic that people are so resilient when things are going bad, I really would like to encourage people to have the mindset when things are going good. Right. It's like I always like to say to people, there's that saying that you either win or you learn. I hate that saying, even though I must say that when I found out that Nelson Mandela coined it, I have to give some respect to its history and its legendary origins. But I don't like it in a sports context. I don't like it in a sports context because I always want people to learn from their wins, too, because I feel like when you win, you sometimes just assume you played great. And a lot of times when you win, you have so many much to learn from it. And I want to teach people, especially women, that when you're winning, you can learn a lot, because when you're winning, you have High leverage. And that's where you can often maximize and, you know, start building up that compound interest that you need for your relationships and your money later in life. And so I really don't want everybody to just be focused on their weaknesses and their down periods, because a lot of times you just got to get through those periods. And where the real gains come is when you're winning and you're crushing, getting more, finding better moves, the best moves,
David McRaney
and you pivot off of that into another thing that really destroys them if they're stuck in a tunneling mindset, is tunneling can create false binaries. And this one, for some reason, really made the most sense to me. When you have reduced things down to two options, you often don't take into account that maybe they both are bad. Maybe neither one is the right one. Which is, I think, why you often ask people to at least add a third, at least identify three candidates. Tell me a little bit more about this.
Jennifer Shahade
Yeah, I think that it's great if you stop tunneling and you look for another option, but sometimes that ends up becoming like a sacrificial lamb. Like, you almost purposely pick one that's not as good to too. That happens a lot in checks. Like, I want to sacrifice my bishop. But let me look at this, like, other terrible move where you can. You can imagine, like, somebody really wants to hire, you know, your. Your partners or somebody, and they really want to hire somebody for a new position. And then they're like, oh, well, here's another candidate, and they purposely bring, like, the worst candidate from the pile so that you're forced into the option that they wanted you to pick anyway. So expanding it to three really keeps you a little bit more honest with yourself that you're actually doing the work of scanning and not just toggling between yay and nay.
David McRaney
Yeah, you talk about, in the book about the. People often try to advise people to do the take it down to two so you can do the flip a coin thing. And I felt your revulsion to this because, you know, supposedly it shows you if it comes up the way you.
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You don't want, you're like, oh, it
David McRaney
turns out you really wanted it this way. You're. It's possible both options are bad. It's both. It's possible you have locked yourself into two things that aren't good for you and that you haven't even considered. Oh, what about number three or four? And that's fascinating to me.
Jennifer Shahade
Yeah, absolutely. I feel that this coin idea can have its use case where you're finally sure that you're. You got your two options and you flip a coin. And it's not to actually pick between them, but that when the coin is in the aerial, suddenly know whether you want it to be heads or tails. But yes, not always gonna work. Not always gonna work. And I bring up the example of naming my son how my husband and I were stuck on the names Leo and Isaac for some time. And, you know, like, more than just, like, you know, I'm not talking about, like, a day. Like, we were thinking about this for, like, a month. And when I found out that it was indeed going to be a boy, so we had to, like, really lock down our search process, I called my dad. And as a joke, because my dad is also a great chess player, I said that we narrowed down the names to Magnus or Fabi because those are the two best chess players in the world at the time. And it was kind of like a joke, like, oh, because I'm a chess player, I. I'm a crazy chess mom, and I need to name him, like, the number one or number two chess player in the world. And then suddenly it unlocked that actually Fabian was the right name. Such a wild experience. It was like, almost right after I made that joke, my husband and I were like, wait a second, Fabi, I
David McRaney
love that your child is going to
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get to tell this story over and over again.
David McRaney
Yeah, this is your. This reminds me, I typed it in, I looked it up to make sure I knew this. Ping something. So it's an old kicker guard quote. Do it or don't do it. You're going to regret both.
Jennifer Shahade
I love that negativity as a form.
David McRaney
Oh, yeah.
Jennifer Shahade
It's funny because I was just texting my friends before this conversation, and I said that, like, God, I can't stand it when people focus on, like, the supposed biological inferiority of women in chess. It's so annoying because nobody is really born to play chess. You have to work at it whether you're a male or a female. And so I feel like the best response to this stuff is, yes, women are bad at jazz, but so are men.
David McRaney
We will be right back after this commercial break.
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the School of Thought I love this place. I've been a fan of the School of Thought for years. It's a nonprofit organization. They provide free Creative Commons critical thinking resources to more than 30 million people worldwide and their mission is to help popularize critical thinking reason, media literacy, scientific literacy, and a desire to understand things deeply via intellectual humility. So you can see why I would totally be into something like this. The founders of the School of Thought have just launched something new called Kitted Thinking Tools K I T T E D Thinking Tools and the way this works is you go to the website, you pick out the kit that you want, there's tons of them, and the School of Thought will send you a kit of very nice, beautifully designed, well curated, high quality. Each one about double the size of a playing card, matte cello 400 GSM
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stock prompt cards and a nice magnetically
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There's so many ways you could use this.
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That's smart50 at checkout. 5% of the profits will go back
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David McRaney
You mentioned this thing sort of using all this to make like a five year plan system. You quoted some people who use this where like, you get, if you're trying to think about your actual life using some of this stuff and you talk about having a primary plan, an alternate plan, and then a one with no restraints whatsoever, no, no people to be accountable to and no financial concerns, what would that plan be? And sort of like put that in front of you and then use your system to commit to it. If you find yourself trying to figure out, what am I going to do next? You just laid this out using these chess ideas, and I love it. Scan for candidates. Label three or four, predict about three or four steps for each one of them. Rank each one one to ten, pick the best of abc and don't forget to falsify your moves. Okay, let's start with this. Let's imagine we're doing this. The first thing we do is scan for candidates. What does this step look like to you?
Jennifer Shahade
Yeah, well, scanning for candidates. Well, first, you know, when you have a big decision, whether it's a chess move or you're choosing between colleges. You know, I speak to a lot of high school groups so they have big decisions in colleges. And one of the things I tell them is that first of all, give yourself some grace. Because one of the things I hear from a lot of them is like, I'm so stressed about this decision. And like then they become stressed about being stressed about it. And I'm like, well, actually it's pretty rational to be invested in this decision because it is very consequential. What you really want is you want to avoid decision fatigue on things that aren't that important, like what color shirt to wear during our interview. So I think recognize that when you have these big decisions, it is correct to spend a lot of time and there is a chance you're going to get it wrong. So I understand that a little bit of stress is going to come through. And so figuring out how much energy and how much time you want to put into this decision is so crucial. And I think in chess it's usually pretty obvious because it's especially to good players when there's a lot of pieces and take. And we can equate this to material situations in life. What school you're going to go to, what job you're going to take, what house you're going to buy. There's a lot of material things at stake. That is what Bezos called a one way door. It's not going to be that easy to reverse once you go through it. You can always reverse, but not easily, not without some additional cost. Same in chess. If you offer me a queen trade. Well, if I do that, I'm not going to be able to get another queen, except maybe in the end game when I promote a pawn. So it's really, it's very consequential. So If I have 50 minutes left and I spend 25 of them on this decision, it's not that crazy. That's actually logical.
David McRaney
Yeah. So we got our array, we've scanned for candidates. Your, your advice is like, at least here, as you're learning how to do this, like just pick three or four. Like, like, yeah, whittle it down to about three and then you can. There's a cognitive load introduces here because we are going to go a little bit into the future, just like a step. What are like three possible outcomes for each one of these? And then you suggest you kind of do that as best you can with the time allotted. And then you rank them. You have a system of ranking them from 1 to 10. How do you do that? What is Your rank from 1 to 10 system?
Jennifer Shahade
In chess, it works out well because you have to do all these calculations so quickly. You have to understand that this is not a number that you will necessarily be married to forever. It is something that is also based on uncertainty. So you're estimating a number between 1 and 10, and then it's just almost like a placeholder so you can compare it to the other situations that you're projecting. Right. And then you do the same process for your second and your third option. And a lot of times, by the way, once you do this process, it's going to Be like really obvious. 1, 2, or 3. It's going to be pretty obvious because one will be like an 8 and the others will be like fours. Right. Especially in chess, you might see that if you play this move, they have a fantastic response and you know there's no other choice. So by the time you're done with your analysis, you're just ready to go and you're confident you make your move. Sometimes the evaluation is going to be very much closer. So you're going to find that, like, at the end of the process, there's two moves that are eights, and you have a tough time deciding. And that's where the question of how pivotal and consequential the decision comes in. If it's not that consequential, if it's not like what college you're going to go to or what city you're going to move to, then you can be confident that you've done a lot of rigorous analysis and either eight that you pick is going to be pretty great. So just go with one of them. Now, if it's a very important decision, that means you might want to call in more research, whether that means more advisors, more digging, and try to find out which one's an 8.5 and which one's an 8.1. Right. So it's a combination of analysis and also evaluating the stakes and how much time you should spend into the decision. Kind of the meta thinking.
David McRaney
My worst habit is you go looking for advice from other people, but you only pay attention to the people that tell you what you want to hear.
Jennifer Shahade
I have that. I have people ask me for advice like that, and you can see that they think I'm going to say no, and that's why they're asking me for the advice. And that's okay, though sometimes they just want that They've already kind of decided and they want your stuff stamp of approval, which is. Yeah, that makes sense. A lot of people now are going to LLMs with these types of decisions, which I think is very interesting. I'm not a. I'm not a big fan overall, only because I think the people who are likely to make a good decision already will probably be able to do it without LLMs, and those who are maybe troubled could make really bad decisions because of it. So, you know, it's more. It's not that I think the LLMs are going to be wrong that often, more just that the type of user could be led astray in a very negative way. Yeah, yeah.
David McRaney
My. My advice there would Be have the LLM not commit anything to memory. Ask it, and then ask it the opposite back to back, and watch it tell you that both options are awesome and that you're an awesome person for asking that question. And so you can get a good feel for what's going on on the other side of there.
Jennifer Shahade
Exactly, exactly. It's very. And even like, small word choices can kind of influence them, which, what, like what you want to hear or what they're going to say in this instance, the one pattern I have picked up on with LLMs that I think is worth noting is that they do have a tendency to advocate for action. They're very action oriented and, you know, agentic, if you want to call it that. They are not afraid to encourage you to make changes. And I think part of that is because of the vast data access that they have, which shows them that people often stay stuck in a rut and don't make big changes. And also they don't have the anxiety of movement and acting that we might have. So I do think that's actually kind of valuable. Once you realize that,
David McRaney
I would like to understand what you mean by this. Sort of like a button on the end of the process. Don't forget to falsify your move. What does that mean to you?
Jennifer Shahade
Well, in chess and in many life situations, like negotiations, for example, one of the reasons it's so important to think sideways is because if you think too far ahead, you're by nature neglecting the most important thing in the process, which is your opponent. So I say, I want to move my bishop, then I want to move my rook, then I move my queen, then I mate you. What's missing? All of your moves. And I will tell you that this is how a lot of kids think. And I mean, bless them, kids are so talented in chess and get better so much more quickly than they used to. But that is kind of how the little kids think. They're like, I. I get to make three moves. And you're like, this is why the game is so valuable for youngsters, because they realize there are other universes of desires and wants and chess moves. And they're sitting right across from you and they're gonna checkmate you if you don't pay attention to that other brain across the table from you.
David McRaney
Oh, that's great. Like, you have to have empathy, sympathy, commiserate. You have to have theory of mind. All these things have to come into play. You can't just have a plan
Jennifer Shahade
and negotiation. It's so important because right like this happens in poker, happens in real life negotiations. If you're trying to think too far ahead, like to, you know, what you're going to ask for two years down the line, or, you know, the bonuses you're going to ask for, and you haven't really gone through the process of thinking, like, what if they don't even accept your number? You're going to get tripped up. So it's much better to, like, really practice and think about what they're going to say back. You know, hopefully you can do it in writing so you have plenty of time to prepare. But I think that is. Yeah, that's, that's really crucial, trying to make sure that you're thinking about their possible responses rather than only about what you want, because that actually helps you get what you want, understanding what they're going to do and what they're going to ask for.
David McRaney
The next thing that we're talking about in the interview is I brought up during the middle of our conversation, this new study that had just come out. And the study's title is Does Chess Need Intelligence? A Study with Young Chess Players. This comes from a journal called Intelligence, and it's where people who study that write papers and get them published. And it's sort of a clickbaity title. It's kind of misleading. But the actual study is very interesting. Basically, they took people and they measured their IQs, and they also measured how many hours they had spent practicing chess. And they found that once you have learned how to play well and you've done the practice, you've done the grind, you've been very persistent, the practice and the grind, and the persistence is more impactful on your competitive chess performance. And so I asked Jennifer what she thought of that study. What.
Jennifer Shahade
What you're referring to is the study that showed that after a certain point of chess success, they were studying elite youngster players, the IQ actually negatively correlated with success. And this is kind of a known phenomenon in statistics, which is called, like the collider effect. And the reason is that you need a relatively high intelligence and a strong work ethic to be good at chess. So once you start looking at a very elite subset, the second variable might win out. It might be true that working hard actually correlates even stronger with chess success. So those players are going to do better than the ones with, like, the higher measured iq, which is kind of fascinating. Fascinating and honestly is a little bit like the principle of chess boxing, that you kind of need them both and that it's more about having them in certain relationships, as opposed to just having, like, all the brawn or all the intelligence. By the way, I mentioned this study to my friend Christopher Chabri.
David McRaney
Oh, yeah, I know.
Jennifer Shahade
And I told Chris. Yeah. And I told him I was going to be on your podcast. And he was. Oh, that's amazing that you're talking about it there, because he said he had great memories of being on the pod with you.
David McRaney
Yeah, yeah.
Jennifer Shahade
And, yeah, I just wanted to. I wanted to double check with him that this, this, like, was correct interpretation, this collider effect. And it's. It's great, though it's also very, I think, encouraging because very few people have super high IQs. Just like very few people can be the top boxer in the world, but a lot of people can get really interested in something that they love. And so understanding that at a certain point, that becomes the more important variable, I think is really cool. And you see this with a lot of people who end up not getting into chess, and bless them, a lot of them end up doing even more important things, like Demis Hasabis, who was a chess prodigy. And at 11 years old, he had this revelation during a chess tournament that what if all this mental energy in the room could be used for scientific or medical advancements? He was 11 and he lost the game. But that revelation ended up being like the seed of his interest in machine learning. And he ended up finding co founding DeepMind, of course, and now is like a household name. There are other examples, though. Even the famous Polgar sisters. A lot of people say that Sophia was incredibly talented. I've heard people say she was the most talented. And she ended up becoming an artist and not being as serious about chess as the other two. Dr. John Nunn, Grandmaster and mathematician, was cited by the one and only Magnus Carlson as being too smart to just play chess. So there really is some truth in it in a lot of different fields. Yeah. Even chess,
David McRaney
You say there are two kinds of chess time. Very briefly, what are the two kinds of chess time?
Jennifer Shahade
Well, there are the time on your clock, because every serious chess game is timed otherwise. And this did happen back in the day, by the way. Players for the World Championship would end up spending hours on a game, like many hours. I think it was actually 14 hours for one game, and they had to shut down the Paris Cafe so the workers could go home at some point. So you have to time the game. But then there's also the number of moves, and that part's unknown. So there's one type of time that's very concrete, like the number of hours in a day and the fact that the world's going to keep turning 365 days a year. And then there's also our own lives where we have an estimate of how long it will go, but we don't know for sure. And I believe it's the same in chess, where we don't know how many moves a game will last, but we know how much time we have on the clock and we have to juggle those two types of time.
David McRaney
That is it for this episode of the youe Are not so Smart podcast. For links to everything we talked about, head to you are not so smart.com or check the show notes right there in your podcast player. My name is David McCraney.
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Date: May 25, 2026
Host: David McRaney
Guest: Jennifer Shahade (Three-time U.S. Chess Champion, Poker Champion, Author)
This episode dives deeply into the misconceptions and realities of high-level thinking, problem solving, and creativity through the lens of master chess and poker player Jennifer Shahade’s new book, Thinking Sideways. The conversation explores what truly sets experts apart from novices, debunks myths about “genius” foresight, and demonstrates how “sideways” thinking – creative flexibility and broad scanning – is often the key to success both at the game table and in life decisions.
“It's not about how far ahead you can look. It's about how far sideways you can look.”
– David McRaney, paraphrasing Shahade [30:10]
"Beauty is in the paths we don’t take. … Living with no regrets means you aren’t thinking sideways enough."
– Jennifer Shahade [32:17]
"If you see a good move, look for a better one.”
– Jennifer Shahade [34:49]
“This is why the game is so valuable for youngsters, because they realize there are other universes of desires and wants and chess moves. And they're sitting right across from you and they're gonna checkmate you if you don't pay attention to that other brain across the table from you.”
– Jennifer Shahade [55:30]
Scan for Candidates:
When faced with a big decision, generate at least three or four plausible options.
“This is not a test where you have to find the best move. This is a test where you just have to give me three options.” – Jennifer Shahade [17:18]
Predict a Few Steps Ahead:
For each option, imagine two or three likely outcomes or responses (limit yourself to avoid overload).
Rank Each Candidate:
Use an informal 1–10 scale to rate options; this helps clarify relative strength or appeal (not a permanent or absolute score).
Falsify Your Favorite Move:
Consciously look for information or arguments that could prove your favored option is not as strong as you’d like.
“If you think too far ahead, you’re by nature neglecting the most important thing in the process, which is your opponent.” – Jennifer Shahade [54:33]
Embrace the Unknown and Flexibility: Recognize the role of chaos, luck, and other people’s actions; don’t over-invest emotionally in perfect prediction. “If I think five moves ahead, but my opponent plays a different move on move 3, then the moves 4 and 5 will have been a waste anyway.” – Jennifer Shahade [24:56]
Intermezzos:
Unexpected moves that upend the expected flow—a metaphor for life’s surprises and the need to stay alert for unanticipated possibilities. [27:47]
Applied Sideways Thinking:
Use candidate scanning for life’s big decisions (e.g., college, career moves, relationships) and avoid fixating solely on binary choices.
Learning From Winning:
It’s just as vital to analyze your wins as your losses, contrary to the “you win or you learn” cliché.
The conversation offers a refreshing and nuanced perspective on expertise, problem-solving, and creativity. “Thinking sideways”—scanning broadly, challenging your first instincts, and remaining flexible amid complexity—applies far beyond chess or poker, offering a compelling framework for better decisions in work, relationships, and self-development.
For further details and resources, visit:
youarenotsosmart.com