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Big money is Making more handcuffs.
you have to save more. It's like you're denying yourself more.
Couldn't be more crude.
In the beginning of the interview, but I-
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You just can't try.
Changes later in life.
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conversing with AI about a new project or a new idea you have.
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This isn't your average business. And he's not your average host. James Alteger Show.
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One of my favorite people in the world, she's been on the podcast before, Jen Shihade. She's a great chess player, great poker player, two-time USA women's champion of chess and a grandmaster in the field of chess. She's author of the new book.
¶ Big money in surprising chunks
Thinking sideways, how lessons from chess have given her all sorts of great skills for decision making. And I, as a chess player myself, I can attest that not only do many of these techniques work.
¶ AI, job security, and choosing yourself
But she even talks about me in the book. So thinking side, how how are you gonna think sideways? Listen to this podcast.
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Yeah, I enjoyed thinking sideways. What a great idea for her book. It's and you had so much research in it mixed with stories. It's really great.
Oh, thank you so much. Yeah, and you so I I I shouted you out, so and I I meant every word that that was a real influence on me.
No, I really appreciate it. When's the book coming out?
April seventh in America.
April seventh. All right. Well, uh it's you know, it's so interesting because I think about chess a lot, like and how I make my own decisions. First off, by the way, how are things going? How's life?
¶ A Note from James
Oh, not bad. Pretty good. I mean poker's going well. The book is very exciting. I mean, there's no better thrill than to like talk to people about these ideas and I'm having a great time.
Are you mostly making money from playing poker or or doing chess stuff or?
Talk about combination of the two. Yeah. Last year was a good year in poker. So it's kinda like with poker it's more it's it's almost like you're your speculative income that you're hoping to do well and then you can like, you know, have a year where you invest and save and then you need something in case that doesn't go well for stability. Right. Yeah.
So that's what I always do is I kind of diversify my income streams. So you have investing, you have cash stuff, different businesses to start. So it's always good to to as you put it, have at least three things going on.
¶ The book, poker, and having at least three things going on
Oh yeah, definitely. And I you were influential for me on that too. And I think the key thing about that is it also keeps your spending low. Because if you have like some basic income that you know you're gonna get for stability and then you have like some speculation, in my case poker, you know that that's not gonna happen every year. So you have to be like It doesn't it it doesn't create this kind of lifestyle creep that you would get if your like salary went up.
Yeah, definitely. Like every time in you I really think the only way to save money and perhaps this is just me, but the only way to save money is to get big money in surprising chunks. And because salary, you're always just gonna spend your salary. So that will never a actually allow you to have more money. Because if your salary goes up, you just you're gonna just spend more. It's just natural.
people have a zero percent savings rate. But if suddenly like you, you, you win a poker tournament or you sell a company, you get a big chunk of money. That's the money you could put away.
Exactly. I mean that's brilliant. And I think that that's a little counterintuitive to people because it sounds like speculation should be like less conservative. and more irresponsible, but it's weird how that actually can be a responsible way to look at things in the long range, because eventually if you work at it, whether it's being creative or investing, eventually you will probably have one of those moments.
And and also if you think about it in terms of psychology, like a lot of people think, oh, if they make more income, they should save more money. But actually what you're doing is When you you know, making more income is this positive thing that you should almost celebrate and yet If every time you make more, it means you have to save more. It's like you're denying yourself more.
¶ Why salary increases don't create savings
And it's it's sort of like making more than becomes this painful thing that, oh, I should be saving more, but instead I can't help myself. I'm spending so you feel unpleasant about it. Whereas the the big chunks That's where you can really save. And then you don't have to punish yourself as you actually increase in your career and you know, however it is, you make more money.
The only thing is you have to work hard. That's the hard part. You have to have some like stable income and then also do projects on the side and and that comes naturally to like to me, I love working, but it it can be really hard, especially for people with a lot of family responsibilities and whatnot.
But that but that's life though too. Like because an income is not really under your control. Like there's a boss, there's a company, there's you know, the market that the sp that that defines the need for your for your services. Most people are paid, let's say, by the hour or by the year, and there's a market for those services. You offer sales expertise or computer programming expertise or whatever.
you can control the demand for your services in that market. Whereas how you invest or or try side projects, you can determine what are the risks. Which side projects should I pursue? So it's sort of like life that your your income, again, it's counterintuitive, but your income is more, is more unsteady than your ability to control your risks on whatever side projects you pursue.
And that couldn't be more true now with the rise of AI, not to get too doomer in the beginning of the interview, but I think more and more people are realizing that yeah, they need to choose themselves. as you wisely put it many years ago, because you just can't trust parts of your salary job are gonna be siphoned off to AI.
Yeah, and and but then also AI might give you more time
and and more ability to decide, okay, hey, this I'm gonna pursue this side project that I can use AI to maybe program a side project or learn more about it or educate myself more about it. So there's just this kind of the give and take of AI. Like it's it's developing for a reason because it's probably net a positive impact on society, but yet many people are feeling it negatively because like you say, it it's taking jobs, it's it's destroying industries. There's this transformation happening.
I agree and I feel like you're right that the one positive and you know, it's hard to control the negatives because that's unfortunately a lot about politics and, you know, regulations that an average person might not have a lot of say in, except at the voting both.
But one thing you can control is like learning new skills, upskilling later in life, which used to be less accessible. Now with AI it's a lot more accessible to just learn things that you'd have to maybe go to to school for before. And that's I think that's
¶ AI as threat and opportunity
pretty interesting because it's not only an opportunity to potentially make money, but it's an also an opportunity to feel good about yourself, you know.
Yeah, I mean, well you have this example in the book that was fascinating to me. This guy, Matt, I f maybe he didn't say his last name or forgetting the last name, but he was forty eight years old and decided to pursue a career as a lawyer.
Yeah, and what was really interesting about that, he he was a successful poker player and writer and he got picked for jury duty and it was in jury duty that he was awed by this public defender trying to make a case for the defendant and he noticed that a lot of the other jurors were just kinda like not paying attention, not interested, but the public defender was trying so hard.
To capture their interest, and Matt was like, That's what I want to do. And so he went to law school at the age of 47, was studying. And I think what was interesting there was he had this idea in his head, I want to do this. And a lot of people have that idea and then it just kind of passes. But what if we just continue that thought to its logical conclusion? And another striking thing about that example is that sometimes it feels overwhelming.
to change directions in your career. But at the end of the day, it's always gonna be chunk. It's not gonna be one thing where you just like wake up the next day and you're a lawyer. You have to study for the Altas, you have to actually apply for law school. So why not just take the first step and see how you like it? See if that desire continues to grow or whether it, you know, burns out.
¶ Reinventing yourself later in life
That's a really great point. Like, like, let's say the process from beginning to end to become a lawyer at the age of 47 is a five-year process. But it's not like I have to say, okay, I'm just putting a big X on my calendar for the next five years. Maybe it's like one hour a day. I study for the LSAT. In three months I'll take the LSATS and then I decide the next step.
And and there's there's no downside. Oh, if I take the LSATs, it's just an interesting story. Maybe I learned something about the law. There's no real downside. I in all these three month chunks from that point, there's no downside to kind of moving forward unless I decide I'm not interested in it anymore.
And that's where AI comes in too, because you can ask all your stupid questions to AI about the process that otherwise you'd have to like monopolize a lawyer friend's time who at some point might m might get tired of you calling them about it. So that is something that really always impresses me. People who may changes later in life and pursue something new. And with all the ills of AI, I think that is one beautiful thing about it, that it's not ageist in the way that our society often is.
If you start conversing with AI about a new project or a new idea you have, it's not gonna be like, oh, you're too old to do that. And so that's actually one of my favorite things about AI.
But you know, it's interesting, like it does remind me of of chess a little bit, this decision making process of thinking in like short term chunks. Like you could be playing a game and of course the goal is to checkmate, but You don't and not every move you make is related to checkmating the opponent's king. Let's say I'm gonna get in the weeds for a second, but I'll I'll try to be high-level about it.
Let's say you one of your first moves is you you do knight to d2. Well, now you got to develop, you have a problem, you have to develop your your queenside bishop and your rook. So you might make some decisions or short term decisions related to well, how am I gonna develop the rest of my queenside? So you don't need to think about, well, goal, I better focus on checkmating the king.
Or else I'm gonna lose. You have to solve short term problems along the way. And that's that's always the way to win a chess game.
That's right. If you're too obsessed with Checkmate, if you're too ups too obsessed with the meaning of life. things get really overwhelming. I did want to put a pin in the ageism thing though, because I just re realized that there's like these lawsuits about AI algorithms being used for hiring that end up being ageists. So It's not that it can't be used to promote ageism, but I don't think the technology is inherently inherently ageist, is what I would say.
I I will share with you a conversation I had with um V Vishwana Vanand where You know,'cause Bishi is a you know, his former chess world champion and probably the oldest person in the top one hundred chess players.'Cause he still occasionally keeps his rate his rating active. And you know
¶ Chess and short-term chunks
Chess players used to be older. Like you had, you know, candidate level of players, Smyslov, Kourchnoy. You know, these guys were in their sixties when they played in the candidates tournaments, or even older. I think Horschler was active till I don't know, I wanna say his seventies, but I guess I don't know for sure. And I asked Bisho about this. Like, why is it the case that now it's like younger and younger? Everybody's getting so great. And he said, the problem is, is that yes.
Chess players used to benefit with age, with wisdom and experience, even though they couldn't calculate this fast. They recognized more patterns, they understand stood a little bit more about the strategy. But now the computer, which is basically built on top of AI, and this is what Bisho is saying to me, the computer basically teaches wisdom to the kids.
'Cause you know, they play through all the algorithms to see, oh, why did the computer make that move? And the kids will figure it out by going through all the possibilities with the computer.
That's right. That's a pattern recognition is able to be absorbed so much more quickly. And a lot of that is developing intuition.
¶ AI, age, and chess intuition
Absolutely.
And so the computer now is teaching me intuition because oh, I can s I can ask myself, why is the computer making that move? And the kids will go over every possible variation. They'll memorize better. Oh, well, if it's because of this, this and this. And they suddenly now have an intuition that they would not have been able to develop otherwise.
But then keep in mind that Magnus Carlson's thirty five, which is of course not old, but it's not like super young, and then Hikura Nakamura is A couple years older than that, even. So the top blitz players in the world are not that young. They're young-ish. Yeah, exactly. And so that's that's pretty im impressive kind of counterpoint. And a lot of people have made the point that I agree with is that people like Nakamura
But specifically Magnus have kind of benefited from both sides of AI taking over everything. And that, you know, he's had this experience of computers being like somewhat less relevant and being able to think for himself. And then of course also the side where he's been able to work with Leland Stockfish.
I mean, obviously computers were chess computers were around even when he was very young, but the the importance of books used to be even higher in those days. And my understanding of Magnus is he just like gulps down books. Like he just like devours then. And what's interesting is his knowledge of chess history is so deep and wide.
Like he has memorized every important game, knows where it was played, like what the players who played it ate for breakfast, like random stuff that you wouldn't expect like Magnus Carlson to need to know to be the number one player in the world. But
How important do you think it is that Magnus and players like that basically started doing nothing but chess from the age of five or six on. So this way when their memory was still very elastic or whatever the term is. They were able to kind of just absorb all this stuff at a very early age. So, you know, if you start later, it's a much more difficult.
Yeah, to be absolutely number one in the world, it seems that starting very early uh anecdotally is extremely important. Right. B and it does I think it's also just having those extra years of pure freedom to play jack. you know, where you're you don't have any other responsibilities, that really is almost like a form of compounding trust. Like when you have it at six, seven, eight and nine, it's very difficult for others to catch up.
You know, and again, I wonder, you know, like I kind of started playing in tournaments relatively late, you know, I was seventeen years old and I felt like, okay, I improved pretty quickly, but then there's things like college and career and and so on.
You can't really you know, it was harder for me to really improve. I just had other things going on in my life and You know, on the one hand I always regret that, but on the other hand, and this is related to your book, I feel like the lessons I learned from chess has helped me in every other area of of my life in so many different ways.
just the idea of making decisions calmly, the idea of what happens when things don't go your way. Like let me ask you a question and and you address this, but when you're playing a game and you make a mistake, now you're losing, I always notice
For myself at least, there's always at least one chance I have. Like the up my opponent's gonna make some mistake at some point, even after they're already winning. Like you always have another chance. And that's a good thing to keep in mind in like other areas of life.
Yeah. Yeah. And also just to understand that if you're not having those moments where you make big mistakes and you're embarrassed, then you're probably not putting yourself in enough tough spot. Right. Like in poker, the truth is that if you're never caught red faced with a bad bluff, it's probably not just because you're a great bluffer, but that you're also not bluffing enough.
¶ Regret, mistakes, and always having another chance
And so I think that that is a good way to make yourself feel a little bit better about those blunders. Cause, you know, I love playing dynamic openings like the dragon Sicilian, like the Nyorf Sicilian, the open Sicilian, m openings where you're gonna make a lot of mistakes. And, you know, you can't then beat yourself up if you go right into the lion's dead. Right. You could play something super dry where you're gonna make fewer mistakes, but that doesn't fit your style. You don't wanna do it.
But I go back and forth on this too, because take a player like Wesley Sow. He's had I think the seventh or eighth highest chess rating in history, but he's not as known as some of the other kind of you know, spectacular players out there because his d drawing percentage is the highest of all like the top players. He plays openings that are very drawish and so on. And sometimes I think that's the better way to play. Less stressful. Go for the draw. And then if you happen to wear in, good.
I agree on one level, if you want to have a like a very long career, I think that's a bit better because like if you look at somebody like Gary Kaspar You know, it's not that surprising that he retired at a relatively young age, Judith Polgar, because the energy that their styles require. is just immense the amount of opening knowledge, memory, and energy putting into the board. I mean part of of course was that Gary wanted to get into politics, but it also kinda made sense.
If you wanna play until you're like seventy or eighty, play something that relies a little bit more on intuition, makes some sense, right?
And So so in your book, you kind of talk about all these decision making styles that that you've learned from chess and there's a couple of things that really stood out to me. One is I really like towards the beginning of the book, you talk about always have three when you're trying to make a decision, always have three choices. And this is not as simple as it sounds. Cause often
You're making you y you know, let's say I'm trying to decide where to go on a vacation. Usually I'm trying to decide between a location and not that location. Or I get a job offer. Usually I'm trying to decide between Taking the job or the career or or the investment or not the investment. I like the idea of trying to force myself to come up with a third choice.
Yeah, I feel like that's really helpful because sometimes when you're deciding between two things you know in your heart the right decision, but s and but the and the reason that you're stalling is all sorts of psychological fears or one common fear is just that people think that not making a decision is different in some way, right? So they would prefer to do the passive thing and hope that something will just come up
and save them from having to make a decision. That there all be like a saving moment. And yet there's also
Oh
often the case that if you think wider, you think sideways, which is why is the title of my book, you'll come up with a third thing. And I I mentioned in my book something, you know, kind of just personal and
¶ Always have three choices
small to the rest of the world but massive to a mom, which is when I was trying to decide what to name my son, my husband and I were just like torn between Isaac and Li Leo. Those are the two names that we had in mind and we loved them both, but we couldn't pick between them. And then we made a joke that we were gonna name him either Magnus or Fabiano after the two best chess players in the world at the time. And suddenly we were like, wait a second.
That's it. And it's just like that that that moment of coming up with a third name really kind of clarified that we weren't deciding between Leo and Isaac. Neither were correct.
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What's another example where the three choices role sort of helped your life?
Well, I mean sometimes I definitely make the wrong choice entirely, like which I know would resonate with you, James,'cause you're not a big fan of people spending all their money to buy a house. One example for me was when I was trying to decide what cows to buy.
I was, you know, really sucked into this process because it's so much fun to look at houses. It's so much fun. It's like you just feel like you're learning all about real estate and you're also thinking about all these different possible lies. And I don't know if you've gone house hunting recently or you like the process at all, but it's also just really fun to look at the places with no furniture in them.
¶ Buying a house vs. not buying at all
'Cause everything feels like this like massive party. You can imagine like just having like a a fun party there. And so when I was In this process, I got really sucked in to two options in particular. And it kind of blinded me to the fact that maybe I just shouldn't buy a house at all. And I should, you know, pick the third option, which is like fold off on this.
and you know, continue to rent or even just like travel the world and store my stuff somewhere. I was pretty young when I bought my first house.
And s you know, but that's really interesting, though like some pipes people miss the completely offbeat third choice, which is that you are stuck into this paradigm of I'm either gonna buy a house or not. But then there's this third choice, which is I can just not even live anywhere. I'll just store all my stuff for a year and travel the world or okay, maybe financial considerations aside.
Maybe just live in Airbnb. It's a different one every month in a different part of the city while all you have your regular job. Like who knows? There's like there's there's a choices that I think people forget to to make.
Yeah, and and actually the example that you gave, like it actually can be l m it as expensive as renting or buying, not necessarily more, because the travel is offset by the fact that you don't have to, you know, have a home base that you're funding while you're not there.
Or or or Airbnbs. You y it's offset by you don't have to buy furniture and pay utilities and and and stuff like that.
Yeah, absolutely. Yeah, so I feel like this way of thinking is really valuable.
You have a great example that I want you to describe, which is the Stanford five dollar experiment, where I really love the dis decision made by the winning group.
Oh right. Yeah, this is one of my favorite examples of, you know, psychological experiments. So a business professor from Stanford, Tina Seelig She has all of these experiments in creativity and developing creativity. And in this one case, she told her students in a business class. to each they each were gonna get a five dollar envelope an envelope with five dollars in it and the challenge is five dollar challenge
¶ The Stanford $5 challenge
was to make as much money as possible. And the gimmick was that you had to spend the five dollars within two hours of opening the envelope, right? And they had the weekend to do this. And so some groups were very straightforward about the problem. and try to, you know, buy items with the five dollars and resell them and make a a small profit, right? If you have a year to do this, you could be like the paper clip guy who turned a paper clip into a million dollars, but with two hours
These gains are gonna be relatively limited, right? And now some other groups realized, so they got kind of like the second stage, and they realized wait a second. This five dollars a red herring. Like five dollars is almost no money. We should just use the weekend to sell our time, right? So we could like pump.
air into tires or babysit, you know, find some other way and then just open the envelope with the five dollars and add it to whatever we made with our time. But the winny group came up with something really brilliant, which was that they knew that at the end of this process They were gonna have to present to the Stanford business school class.
how much money they made and how they did it. So they sold their presentation time to an advertising company. And and then they won m made m one made much more money than any of the other groups. And I th just a really brilliant idea of creativity. I'm kind of seeing that sometimes by reframing the question, you can get a much better answer.
Not only reframing the question, but forcing yourself to have more options, to think meta in terms of your options. Like not just, oh, here are the ways I could spend$5 to make more money, which was kind of like that first stage you mentioned. What is every component of this problem and what can be sold? And you know, which of these components can be sold? There's there's the money I'm getting in the envelope, there's the w the weekend time, and then there's this.
Amazing thing, this ability to prov pr present to Stanford students, which many be of the groups probably didn't even think that that was an an asset that they had.
Yeah, because it's like a baseline if you go to a school like that, like this everybody is probably kind of assuming that that's like normalized, but in in the world at large, of course, it's not. And that's like the the value of prestige. is very high. And ask it again to bring up AI because it's always in our minds. I feel like the value of prestige and reputation is only going up because it's harder to cold call people now in some way. Right. Because a lot of people are
more heightened to the concern of scams and AI writing and AI content. And I think that being trustworthy now has really risen in value.
Yeah, and so... For yourself, you're like this essentially an athlete, like a mental athlete, chess, poker. Like let's say someone wants to emulate what you're doing. Oh, I'm gonna be a chess player, I'm gonna be a poker player, like what what kind of basic skills Other than chess, the specifics of chess, other than the specifics of poker, what do you think you had to learn or at least deal with as you were, you know, going on to to be a champion of both of these activities?
So many skills. Definitely one that came rather naturally to me is the ability to focus. But for for many people that'll be a a hard one. The ability to focus a hundred percent when you're playing.
¶ Focus as a competitive advantage
Because that's your moment to shine. I think a lot of people see something like a test, a presentation, a chess game, a poker game is like a where you're just gonna be tested on your knowledge. No, no, no. It's much more than that. It's an athletic performance. where you need to bring your energy in order to do more than what you studied, right?
That I think is a really crucial skill that just kind of came more or less naturally to me. Like I feel like when I won my various titles in chess and poker, oftentimes I was not the most knowledgeable player at the table. But if you look at me in like these pictures, you see like I'm like completely locked in, as they call it now, in the zone. And I feel like that gave me like an extra couple hundred rating points, honestly. You know, it's just uh it makes you really tired though.
Yeah.
There's always a cost. So that that is that's a key skill and people are really noticing now that with the advent of massive distraction on cell phones that this skill is more and more important. The ability to completely focus. You know, I'm actually looking at my bookcase over here and I see the book Deep Work by Cal Muport, which is all about this. That as People get more and more distracted, the ability to lock in is of increasingly increasing value because it's a rare scale.
Yeah, that's a really good point. That right now, I mean, again, there's AI, there's the internet, there's all these things that distract us. And because of that, you can identify these skills that can very not I don't want to say easily, but
¶ Deep work in a distracted world
There are basic skills that can help you stand out, like focus being one of them. And so how do you log in? How do you get more focused in general?
Well, like I said, it it comes naturally to me when I play chess and that's why I love keep teaching chess to children, because I feel it actually grown ups too. For chess it's like almost like a incubator or flow. like f the flow experience meaning that like you're completely absorbed by whatever you're doing. I think like chess can really bring it to people very, very easily at a very young age, as long as you like chess.
If a child likes chess, once they start playing, the size of the board and the mental challenge that it presents. is honestly like the perfect incubator for flaw. And so you will just like kind of automatically feel that. And then say you give up chess a couple of years later, fine. But what I'm hoping is that that child remembers that feeling.
and is able to emulate it at different stages in their life. If you're older and you struggle with the flow because not as much because you don't know what it feels like, but it's like harder to reach because of distractions. I think that's where you wanna really look at your cell phone diet and see if you can come up with systems.
to get yourself away from your phone and your notifications in the periods of the day where you're finding flow most easily. For many of us, us, that's in the morning. You want to protect your mornings? Sure, you might have to check your email in the beginning of the day because it's part of your job. But if you can find a two hour spot like
think it's very common nine to eleven AM people are very, very locked in and their brain is kind of like really flowing. That's a time where you wanna put your phone aside and your email aside and try to do something that you really care about. And for me actually, one thing I've started doing is a lot of my interviews that I'm doing for my book, I do on my phone. And one reason is because that blocks all notifications.
Yeah, exactly. So I'm doing this interview with you now and people could be texting me about all sorts of stuff, you know. Something could be happening in the the world, the glob global politics, but it's it's not gonna pop up. I'm not gonna get any notifications and That's the kind of system people want to create. Like in my book I talk about how Tim Urban, a podcaster and writer, uses a chess clock, even though he doesn't really play chess, to measure out flow state.
And what he does is he sets a clock in the beginning of the day for four hours to do deep work and four hours to do like other stuff. Like emailing, chatting. He I think he works from home, so like washing the dishes and listening to music, whatever, right? And that he hits the clock. for the deep work when he's locked in and then when he's taking a break, he hits the other side of the clock to kind of try to divvy up his day like that.
Yeah, similar to the and you talk about this in the book, but similar to the Pomodora technique, which assumes you can f focus for at least like forty minutes, then you take a ten minute break and whatever. Yeah.
Yeah, I I think those I the Pomodoro didn't work as well for me, but 'Cause I just feel like because the chunks are s are relatively short, sometimes like the process is a little distracting. But the point is there are there are kind of permutations of this and you can kind of try what works best for you.
If you had to learn like a new skill right now, like not chess, not poker, but any other skill, what what would be what would be the how would you think about it? Like what how would you start yourself off learning this new skill?
Well, yeah, it's interesting because I'm one of those people who had never written a line of code before. In the last couple months I've been kind of working with Claude on various projects and it's been so amazing because not only do I get to see things come to life, but through this process you learn about coding. And so that's getting me some thought into adult education and how you can pick something up.
¶ Learning new skills with AI
So that I guess like suppose I wanted to learn another language, which I would like love to do. I speak some Spanish, but I would love to learn like Arabic or Chinese. I think what I would do is I would start By coming up with a strategy to find something that I already love, like chess or poker, and to
chess and poker broadcasts in that language. So that would definitely be my first step. And I would like to never thought of it that way. Yeah. And I think I would absorb a lot that way because I already know what's happening in a chest position. So I would be able to kind of see what they're saying and it would like match my brain.
And then I would definitely work on use spaced repetition and vocabulary drills with with an app with an L L N. And I I I would probably personalize it. That's the nice thing about L L M that you can create your own. Training materials quite easily and that helps you because when you create your own training materials, it makes it more personal to you.
would you do that? Like how would you ask it to come up with personalized training materials?
Well, you could create like a simple code for like uh, you know, chess and poker vocabulary drills. Right. And then yeah, and you honestly you it you would have you'd have an HTML file like fixed like like an hour later that you could continue to edit. So then you would learn about coding as well as whatever you're trying to learn.
Which is
Yeah, which is a lot of fun. And honestly, I I read a study by the Harvard Business Review a couple of weeks ago that's now going viral in all the different major publications. There's something about it in the Financial Times and Wall Street Journal. I've seen it everywhere now. And it's basically The idea that AI is making people more tired and more overworked.
And it sounds negative, but I'll say there is also a positive. The reason for this is because it's kind of putting people in this dirt deep work state for a higher percentage of the day. Because the AI ends up doing some of the grunt work and so you end up kind of like in the more absorbed state longer. And that's very tiring, you know? So that's something to think about.'Cause when I was working
Because you can, it's very like let's say I want to learn something. So I asked AI the first question, it's it gives me three or four paragraphs. There's something I don't understand. Now I have the
¶ Why AI can feel exhausting
And the next question gives me another three or four paragraphs. There's something I don't understand. So I can keep diving in. And this is kind of like what you how how you talk about the flow state in the book. I'm always Just I'm hitting kind of like the very
Not
Not beyond what I can understand, but at the very top of my level of understanding. Oh, here's something I don't understand. Here's the first thing I don't understand. So it's it's right above my skill level I could start to keep asking about. So I could remain in that flow state while asking questions to AI for much longer because I'm directing it.
¶ Why large language models are bad at chess
Exactly. It's very tiring. And that's one interesting thing I found about when I was trying to play Chat GPT and chat and kind of understand more about ChatGPT and Claude or Gemini via playing chess against them. For your viewers who might not know this, because it's a little bit surprising, the LLMs are very bad at chat.
So they're like less than a thousand level. And the reason is that they've never tried to extend their intelligence to chass in the way that they have with math. So it's not like they've like plugged in a stockfish engine or allowed the AI to consult stockfish. or the LLMs to consult stockfish. So they're really just basing their chess moves on pattern recognition and, you know, probabilistic output. Like what would probably be the right move if you play night takes D seven.
They they know the rules of chess, but it's very hard for them to make good moves over an extended period of time. And what I noticed was that it started to cheat against me when I made certain captures against it.
How would the tool for cheating be the cheater?
Well, what it would do is like suppose I play against cat GPT and I play like Queen Takes D seven and I'm just winning a free knight because like their knight is already gone. It's gonna it's gonna say like night takes D seven. I'm like, wait, you don't have a night anymore. And it's gonna like, Oh, sorry.
And so Mick, this is this is quite typical. So it's basically confabulating. It's saying like most games of chess history, if you play Queen Takes D7, I usually have a knight to recapture that queen. Right? So i I don't this time, but usually I would. So that's the move I'm gonna try to play. And so you correct me. Uh so that's kind of more like confabulation than cheating. And confabulation is usually a word to describe people who have gaps in their memory and they try to fill in the sequence.
with the most likely explanation, right? Happens a lot when we try to remember our dream. happens with people with memory gaps. But even when we try to remember a dream, a lot of times we're confabulating. We don't really remember it. We might remember like two things from the dream and then we just kind of like thr make a story to thread them together. That didn't actually happen in the dream.
So this is kinda what the LLM is doing. But what really struck me is that after I played this these games with it and it kept hallucinating, cheating, confabulating, whatever you want to call it. I had this idea that I would now try to play it and play like a rank beginner, like 200 level. Just play the worst modes possible. And so I did this and what happened now was that The LLM cheated, but in my favor.
So it brought me up to its level. Yeah. So I tried to get like fools mated and then it was then it was like saying like it didn't give you check mate. It was like, oh, I can play like my I already put my pawn to G four and it was like, Oh, you can play G three here. So it's almost like it was making me its level no matter what.
And that's something people have noticed is probably the biggest promise of AI for education is because there's a lot of dangers of course with it that will converge, that'll damage the teaching profession. There's definitely some dangers, but I'd say like the number one positive. especially with adult education, is that it meets you where you're at.
Yeah, I think I think, you know, the AI in general is programmed or not programmed, but it it it it wants to say things that you're gonna like because then you're gonna continue talking to it. So it's it's gonna wanna be at your level. It's not gonna wanna be too high above your level because then you'll go somewhere else for your information. And it's not gonna wanna be too low because then it's not useful for you. So it's always trying to make you mildly happy.
And and that's the the the focus of its responses.
And that's why it's so good at teaching things at a beginner or intermediate level. Because uh many topics it's just not good enough to teach like the best in the field. So obviously it's not gonna be able to do that. But if you're trying to learn something that you never got a chance to study in high school or college. like math, coding, anything like that, suddenly you can basically take the one on one class and have it personalized to you, which that's pretty cool.
And you've been using it for coding. So let me let me ask you. I'm a coder. Like I went to school for programming and I have my first few jobs out of school or I went to grad school for this. I wanted my first few jobs outside of school or programming. But I've never used Claude or or any kind of AI coding. So let me just ask you, like, how do you do it? Like so I go to Claude
And I say, oh, write me a program that, you know, is an e-commerce site. Then what is it what happens? Does it write the code? What do I do with the code? I mean I'm asking like very basic questions here. Does it create a place where my store exists? Or what do you do?
Well generates an HTML file basically. And then you can continue to tweak the HTML file. And then if you wanna do some things that are more complex, I I do pretty basic projects like creating like chess games or mini games and things like for instance I I created versions of my online chess games that I created years and years ago, like hula chess and roulette chass. And then I also created a uh
And where does it where does the code now like does the code run? Like where does the code live?
Well, because I have a personal website I can always just stick'em up there. If you don't, then there are all sorts of platforms like where you can like crew you I mean, you might as well just get yourself a personal website and then stick them there. Yeah, that's probably the best thing to do. But there are also places where you where you can put your your games in your websites to test them as well if you don't wanna make that investment.
But you can just test it on your browser too. So that's pretty fun. And I one thing I made was just for my like social media, I was kind of like, For some reason Canvas sometimes can be counterintuitive to me. And so I was like, oh I just wanna make my own like my own thing where I can just like create my own quotes and stuff just so it's like very fast and I don't have to like navigate this. That it's really good at too.
It's not the big great greatest designer though. So I feel like you do need like some design skills or some visual assets that you like that you can use when you try to make things with it.
But it'll get better at that though, probably.
Probably. Yeah. Yeah. And also maybe it's good that like there is a lot of concerns with IP theft, lots of lawsuits. So if you can actually use your own photos and images that you generate as like the backdrop for something, it's probably the safest. 'Cause you never know when there could be like a a crackdown. And maybe that's one of the reasons why the images are so basic that it generates now. Not really sure. But yeah, that's
It's kind of how I go about it. And I've really learned a lot. I've only been doing this for a few weeks. Apparently, Claude really just really stepped up the game with this so that somebody who's never study this can really start working with it right away. They they call it vibe coding. One of my sub stacker that I just discovered talked about this and says that once people realize how powerful it is, they tend to have like a
sort state of mania because like all those ideas that have kind of been incubating through their adult life that they just would never be able to do because they don't have the skill set, suddenly they can just do it. And that's really empowering.
🎵 Music
You know, you mentioned cheating earlier and and you talk about cheating in in the book and obviously I think in April the Netflix is gonna have this documentary about, you know, Magnus and Hans Niemann and the whole chest cheating scandal. Like what Like why did you talk about cheating in this book? So this is a book about decision making. What's the r relevance to the to cheating?
That's a great question because that's what my editor said too. Fun story is that I used to have an entire chapter on cheating and she was like, This is more about life skills. How is cheating a life skill? And I was we because obviously I'm ta telling people not to cheat. Right. Tell people why not to cheat, but she thought it was a stress.
¶ Ambition, values, and cheating
that like putting a bunch of stuff about cheating in a book where the whole thesis was don't cheat and like don't be paranoid she thought it was a bit of a scratch. So what we did actually is we kept some of it But we put it in a chapter about ambition. And the idea is that if you are overly ambitious and you forget your real values and like why you're trying to achieve the stuff that you can, you're very vulnerable to temptations like Jade.
Right. If you believe in the process and becoming the best version of yourself, then not cheating is gonna become very, very naturally to you because why would you cheat? And so what I did for this book, which I really love, was I talked to some teeth. some reform teeter. So people who cheated in chass and then they had a change of heart. They realized that what they were doing was bad and they quit cheating.
And one thing that all the cheaters had in common, I would say,'cause there was a lot of differences as well, but one thing they had in common was they tended to think a lot of other people were cheating. So this is quite common. If you think that other people are cheating, you're more likely to cheat.
because you feel like it's kind of like a wink wink, everyone's doing it. If you don't do it, you won't be able to keep up with the the others, right? In the same way that like steroids and some sports A lot of the excuses have been everybody's doing it. Nowadays, AI use and writing papers in college is apparently just
you know, complete so rampant that they can't even assign essays anymore. Right. So this was something you found. And when people decided to quit cheating, a lot of the time it was just'cause they got caught. And sometimes they also realized the potential impact could be much, much greater than what they originally intended. So for instance, one of the cheaters cheated online.
And he realized that somehow work could get out to people in his IRL circles and it could damage his reputation in real life as well. And so there were there are different reasons that people quit, but I found it interesting that there is usually a common thread that they believe there was rampant cheating.
That that is interesting. And Ye you know, I wanna I wanna just for a second pretend there are positive aspects to cheating. And and one of them might be just figuring out how to cheat and not get caught. Let's see if let's say even in real life cheating, cause the cause the Hans Magnus case. Really involved did did Hans cheat in real life? And it's actually an amazingly difficult problem. You have to be really creative.
Cause'cause I guess the room they were playing in had no windows or a very small window. And how would one cheat? It's a very difficult problem to figure out.
¶ Chess cheating, Hans Niemann, and online trust
Well yeah, I don't think that Pon cheated.
I I don't think so either, by the way.
Okay, yeah, if you but if you did want to cheat, let's just say like hypothetically, the before the Magnus Hans incident, the measures against cheating were much less hard. So it was easier to teach. Like for example, they used to have a real-time broadcast. So the exact time that you're making a move on a chessboard, it would be broadcast to millions of people on the internet, which can include, of course, Stockfish, Leela, all the strongest chess AI in the world.
So if you had a bad actor, like relaying that to somebody via beads, more likely in somebody's ear than in other parts or in their shoe, you could like in real time relay via Morse code or by some sort of code, what the best move is. And yeah, that's I think a a serious concern. That could definitely have happened. Now with the broadcast delay, it seems much, much harder. I don't really know how you could do it with the broadcast delay.
And you know, the other you know, Hans one thing that came out was that Hans did cheat when he was younger and on online, not in real life. We don't know of any case where he cheated in real life, but when he was younger, like I don't know, thirteen, fourteen years old on chess dot com And his his argument there was that he wanted to get a higher rating so he could challenge himself against higher rated players. I mean, I would say that is unethical. I mean he shouldn't have done that.
Oh yeah, that's actually really common justification for cheating. And some of the cheaters I spoke to in the book, they're anonymous, but of of course Hans was not one of them. A lot of them use the same justification. They said they wanted to play against stronger players so that they could become strong.
and that then their level would catch up and they wouldn't have to cheat anymore. And and you can see that same kind of logic with people who might cheat or lie on a resume hoping to get a job, thinking It doesn't matter, once they get the job, they'll be able to make up for this these lies that they told in the in the resume. So it's also a very, very common justification.
But also it could be like in some areas of life it could be a method of learning. So so my one of my daughters was gonna do an open mic for for stand up comedy and I told her an idea, which was take a joke which has worked for other comedians, like steal a joke and do that joke and see if people laugh. And if people don't laugh,
It means you're the reason. Because we know the joke's funny. In this case it would be the joke rating part. She doesn't have to focus on the joke rating part because that's been done because she's stealing a a successful joke. And she and and so she isolates the the delivery part. So if it doesn't work, she knows she has to work on the delivery. If it does work, she should probably work on her writing and not her delivery. So to so I think
And of course her response to me was, Well, that's you know, you can't do it. You can't steal a joke. And I'm like, this is not you're not going on Netflix here. You're just doing an open mic at a comedy club. There's no real downside. for you. So so sometimes the the same idea or or another another case where cheating happens is in magic acts. So a magician, if I'm let's say
Let's say you're you're picked out in an audience and I'm um a mentalist trying to figure something out about you. Well I I'm on the stage, so I'm not Googling who you are, but perhaps other people in the audience are goo who are working for me are Googling who you are and they'll make hand motions or do something, i.e. they're cheating, to kind of signal me information about you. So some areas of life, the same techniques that would be considered cheating in chess.
could actually cr you know, enhance learning or or or provide ammunition for a career or whatever.
It's funny the magic example I think I feel like that's not exactly cheating, but the example about your
It's not cheating in magic, but it would the same thing would be cheating in chess.
There's a victim though. Like in in magic, there's no victim. Like the audience is not a victim. They're just kind of like they're confused about how it happened and maybe some of them realize some of them don't. Whereas if you're cheating in chess, you're the person who's getting cheated is the victim and their confidence might be a little bit damaged, their
They're a little bit upset. They've been studying and they're just losing to this lower rated player. And I've seen it happen. I've seen people who get cheated live. You just you know, because you find out later that it's a banned account. And I remember watching one person where this happened and
They were they were frustrated. They were just like, damn, they played so good. I thought I was good at this opening. It's it's gaslighting. You're gaslighting the people that you cheat against, I think.
And even in real life, like let's let's say I'm playing a kid and the and for whatever reason the parent is allowed in the room, depending on what side the sometimes I'm thinking. Oh, if the parent is on the left hand side, the kid don't maybe gets some information and if the parents on the right like I like I just the concept of cheating really could get me down, particularly when I'm playing kids for some reason.
Yeah. No, the the fear of cheating is really abhorrible also because it stops you from thinking clearly and from getting that flow state, which is one of the beauties of jazz. I think in in uh comedy I feel like Isn't there like some famous jokes that people uh all tell, like the aristocrats joke or
So there there is some jokes that are made to ba basically. I've actually seen and and this is gonna be astonishing, but I've actually seen Jerry Seinfeld steal almost word for word a George Carlin joke. So it happens in in comedy, but it's very rare.
Yeah, but I think the difference there is like the the it's it I think it would be an interesting experiment if she reveals to the audience what she did at some point. But just doing it and not predating I mean you say that it's not like you're on Netflix. But the f the thing is people go backwards in time if she becomes really successful in comedy, they could like dig up this video or something. So I can see like the fear and the reputational pop.
Which we saw in the case of Hans Niemann, right? Like he was doing these cheating before he became famous. And then, you know, the chickens came to roost when he beat Magnus in a big game. And that's actually like something that one of the cheaters of my book said. It's like you realize that you're doing it in what seems like a low cost game, but then later if you become successful
Like suddenly people are bringing this up. In the same way that people who become really successful sometimes get quote unquote in trouble, slash at threat for cancellation for some tweet they made offhand like, you know, a dozen years prior.
Do you think do you think Hans actually got better in chess because of this scandal? I mean, he's like top twenty in the world now in Chester. It's kind of astonishing because he was just he wasn't even a GM at the beginning of COVID and he just like shot up and then there was this scandal and then now he's like a top twenty player. He's like practically uh you know candidate level.
Yeah, I think he's super ambitious. And honestly, he was able to do something that I think is quite admirable, which is take the good from the scandal, which was all this massive attention. He there were a lot of Hans stands. There were a lot of people who took his side because they thought that, you know, there was never any evidence that he cheated and he had a lot of haters and a lot of lovers.
And he was able to just kind of like focus on the positive and you know become this like megastar. And you know, it's it's it's been a pretty incredible, I think, show of his scrappiness. Now, I I still think the one thing about it is like I feel like when he cheated, the the times that he ch he admitted to cheating, it was already the chess was becoming more popular online and there was potentially money to be made by having a a high online chess rate.
So I still feel like it wasn't meaningless games. And that's the one thing I don't like. I don't like that when he talks about it, he says like these games are meaningless. Because, you know, they're not meaningless to the people who got cheated.
So sometimes that's like the one thing when I see the interviews like he did an interview with Pierce Morgan and he's saying it's it's meaningless. It's like, you know, you can own up to it and say, like, yeah, I cheated. I was younger then, I don't know. And like one of the tears in my book says He says that he steals like tournament chat.
where you play a person and you sit in front of them and you look into their eyes, he feels like it's a church. He wouldn't cheat there. It's like so spiritual. The online chats. That's removed and he didn't feel that way about it. But that as time passes, you see these formats becoming closer and closer together. So I feel like that's a completely legitimate explanation. I didn't see it as real chess. Now I do. Like I just why can't people just admit that they made a mistake?
Well, and to your point, there is a victim. Like it's it's oddly it losing to a cheater is different than losing because you never have a chance. Like it's really disheartening. To to at the end of a game like what the heck just happened there? Like I never once
had a moment to breathe even. I get and it and and if you play them multiple times and you lose each time y and you never once have a chance at any of these games, it's like what I was saying earlier. Like even when you blunder a game, you usually have you know, some chances afterwards. There's usually some upside, you know, oh, I lost a a piece, but now I have some a tiny bit of compensation to play.
But against a computer there's nothing. And against a human that you don't know is a computer, it's it's very disheartening. So so being a victim to cheating is very painful online. But I was just wondering if the if the skills of cheating and chess could be used for for other things like like
again, in this example of a of a magic act or or in the stand up comedy situation. But, you know, one one other thing in your book that I thought was very interesting, and there's many things that are interesting, but this is another one, is It's very emb you s you said you mentioned how the best players are are spend more time Trying to falsify their moves, meaning trying to to before they make an actual move, they try to prove to themselves that the move is bad.
And you know, Maurice Ashley, you give an example on the Daily Show, and Mauri Maurice is a grandmaster. He he says he's always aware that he's got an opponent. And I think weaker players don't always play that way.
¶ Falsifying your own ideas
Exactly. And that's kind of one of the genesis of my title, Thinking Sideways, that if you think too many moves ahead in life or in chess, you're often forgetting about the world, the other guy. The all the things that your family members, your boss, all these people that what they could be thinking and what they might be reacting. And that is why it's so important to be flexible and to try to steam steel man your various arguments, your chest moves, your ideas.
And yeah, it's really a fascinating show. And the way they tested this, by the way, in chess, they there was a couple of research studies and there was also a whole book written about this. They actually had players look at a chess position and speak out loud. And they measured the number of times that a player would try to falsify their moves and consider their opponent's options. And it was a direct correlation between the strength of the player and the amount that they did that.
All the way up to super grandmaster Mickey Adams, who was the co author of a book about this effect.
Yeah, and I I'll I'll give you my own personal example from this. I was once talking to Jan Gustafsson, who's like a twenty six fifty grandmaster, and he showed me a chest problem. And I gave an answer and he said, Oh, that's correct. And I was all proud of myself. But then I I I think I was sort of lucky because then he just starts asking me questions like, What if this? What if this? What if this? And these were questions I hadn't considered at all.
And I just again, I was right, but I didn't really have all the answers to his questions. I just happened to have kind of gotten the right move. There was some instinct, but I saw how he thought was much different than me. He was trying very, very hard to prove the answer wrong, you know, and asking questions that I hadn't even considered. And that made me think he had a very different style of thinking about moves than I had.
Oh yeah, Jan Bruce Dustin, one of the great chess commentators and also chess opening theoretician.
Yeah.
And and and and again in life it's really important. Like I think entrepreneurs don't think of this a lot. Like they think of a good idea, but they don't think of all the ways the idea could be bad. And so they might spend two months, six months, two years pursuing an idea without Really trying to falsify the idea.
Yeah, although you probably need a mix of both'cause otherwise you you wouldn't there's a lot of things you wouldn't do in life if you thought of only about the bad things that could happen. I feel like in an organization you need teams where there's somebody like that and you actually give power and responsibility to that person.
Yeah, so how do you how do you overcome that? How do you find the balance? How do you find the balance in life?
It's really hard because that can freeze you, that type of thinking in life. And I think part of it is compartmentalizing it so that you're not thinking about all the things that can go wrong all of the time, but that you are.
Uh
trying to give it its due and then move on and have this delusional confidence that everything's gonna work out. And be also aware that you're gonna make mistakes despite the skill.
¶ Balancing doubt with action
Because in chess, like if you try to prove why everything is wrong and, you know, think and think and think and think about this, you will lose on time. So you actually have to make moves. And to use another s life skill that I think we can learn from AI, one thing I really noticed about AI is they're constantly telling you to do things. You know, like the whole cliche of
just do things. Very popular phrase in Silicon Valley now, right? Just do things. And I noticed that when I sometimes talk to AIs about different ideas and about like you know, different things that I want to do. They're always like, just do it, just do it, you can do it. And they're also very quick. Like if you keep asking about her, like, you should have sent that email already. Why are you still talking to me about this?
And I find that very interesting. I'm like, for some reason their data is showing them their vast amount of data is showing them that people should make decisions more quickly. Like a chess player. We n we can't just sit around and think forever. We have to actually make moves or we will lose on time.
And it's a really good point because I get I think what computers show in chess, and this is probably true for for every life decision really, is that most decisions are pretty good. Which is why they don't have to overthink it. Like you mentioned in in the book, how Magnus Cross isn't the best player ever.
has basically said, hey, you should try to checkmate your opponent in three roofs. The the so-called scholars mate, which is a really re we used to think uh like we would grow up learning this is a really bad way to play. But actually if you put it in the computer, white's still kind of ahead.
Even after you make these lousy three first three moves, but it's still like a little bit it's even basically. It was it didn't really ruin your game to try to check main in three moves. But but you'll learn, you know, really fast as a kid.
Oh I love that.
thought by Magnus. And it you know, as a poker player, it made so much sense to me after I heard him say it to my my son was in a class. And Magnus said, yep, we'll go for the four move made. And the coach is like, but the idea there is that you wanna have this philosophy of winning. You want a child to want to win.
¶ Why ambition matters, even if the first move is crude
You don't wanna like try to abstract everything and say like, Oh, you know, you shouldn't try to checkmate your opponent quickly because Technically, there's like a slightly better opening where your position will be better and you'll learn more if you continue to do this. Like sure, that makes some sense.
But there's also a way in which a child wanting to win is something we should celebrate because if they keep that spirit, they're gonna keep playing chess longer because they're gonna win more.
Yeah, it's and I think by the way, I think this is a really good life skill. You see, like Elon Musk starting businesses, he's like, Yeah, what let's make a rocket ship to fly to Mars. Like it sounds insane. Just like checkmating someone in four moves and chess seems like it should be an insane thing to do. And yet it kind of c is a starting point for ambition and curiosity and and learning and and so on.
So it's a it's the it's a good way, a good way probably to make decisions. It's like, yeah, go go for the gold while you can and then learn back up and learn from that.
Absolutely. Absolutely. One thing I write about in my book actually also for the inspired by Magnus and all of his equity driven kind of work when he plays chess. is this idea of when you're being successful in life, being relentless and like working really hard, because I think there's so much attention paid to like resilience and grit.
And like continuing to work when you fail. And that's important. But I think even more important when I've noticed in my career is that sometimes when you're having a tough period, you just have to get through it. You know, but the other type where you're having like a golden zone, that's actually where you should go really, really hard because your your spirit is so strong and people can kind of vibe on success.
They feel it. And that's where you have much more opportunities. And I think that like instead of celebrating, sometimes I look back at my life and I'm like, when I had that win or I had that win, instead of celebrating, I should have just kept going, kept going, kept going.
¶ Work harder when things are going well
So celebrate when you fail and work harder when you
Yeah, that is really interesting. Well well look. Jen, you've been author of so many great books. Chess Queens. What was the what was the instructional one called? Play?
Play like a girl and play like a girl.
Girl. Yeah, I love that book. And you sent that book to me like 10 years ago for my girls. I really appreciate it. Now, this one thinking sideways. Such a great book. I've seen lots of different books about decision making. This is so great how you you interweave all the stories and your real life experiences with.
you know, very concise explanations of the research and studies and actual recommendations of what to do to take advantage of this research in real life. Such a great book. I highly recommend it. You know. As always, I mean we've known each other a long time from the chess world. Thanks once again for for coming on the show.
Thanks so much for having me. You are such a thinking sideways guy. So I'm really flattered that you like the book because it's written about people like you and you are mentioned in it. So thanks again for having me, James.
¶ Final thoughts on the book
Yeah, no, I appreciate it. Thank you.
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Säg det med kyckling. Gör relationsquizet i McDonald's app och låt en de sköta snacket. Vi ParGIP är med våra kunder hela vägen. Från planering till leverans och montering. Eller tills du känner att du har allt du behöver.
Ursäkta, kan vi släppa handen nu?
Ja, just det är ju klara. Se bara till om du också behöver en hjälpande hand. Och oss får du mer än bara inredning. Du får avgivning hela vägen. Välkommen.