Navigating Happiness, Success, and Self-Prioritization in Modern Life

Happiness is being satisfied with what you have. Success comes from dissatisfaction.

Is success worth it then? Oof. I'm not sure that statement is true anymore. Like I made that statement a long time

ago and a lot of these things are just notes to myself and they're highly contextual. They come in the moment,

they leave in the moment. Happiness. Okay. So very complicated topic but I always like the Socrates

story where he goes into the marketplace and they show him all these luxuries and fineries and he says how many things

there are in this world that I do not want right and that's a form of freedom so not wanting something is as good as

having it in the old story with Alexander Dionius right Alexander goes out and conquers the world and he meets

Dionius who's living in a barrel and Dionius says get out of the way you're blocking my son and Alexander says oh

how I wish I you know could be like Dionius the next life and Dionis says that's the difference I don't wish that

I could sorry Dioynes Dioynes Dioynes says I I I don't wish to be Alexander so two paths to happiness and uh one path

is success you get what you want you satisfy your material needs or like Dioynes you just don't want in the first

place and I'm not sure which one is more valid um and it also depends what you define as

success if the end goal is happiness then why not cut to the chase and just go straight for

uh does being happy make you less successful? That is a conventional wisdom. That may even be the practical

earned experience of your reality. You find that when you're happy, you don't want anything. So, you don't get up and

do anything. On the other hand, you know, you still got to do something. You're an animal. You're here. You're

here to survive. You're here to replicate. You're driven. You're motivated. You're going to do something.

You're not just going to sit there all day. Unlikely. Some people do. Maybe it's in their nature. But I think most

people still want to act. they want to live in the arena. Uh I found for myself as I've become uh happier is a big word,

but you know, more peaceful, more calm, more present, more uh satisfied with what I have, uh I still want to do

things. I just want to do bigger things. I want to do things that are more pure, more aligned with uh what I think needs

to be done and what I can uniquely do. So in that sense, I think that being happier can actually make you more

successful, but your definition of success will likely change along the way.

Is that a realization you think you could have gotten to had you have not had some success in the first place?

At least for me, I always wanted to take the path of material success first. I was not going to go be an aesthetic and

sit there and renounce everything. That just seems too unrealistic and too painful. Uh, in the story of Buddha, he

starts out as a prince and then he sees that it's all kind of meaningless because you're still going to get old

and die and then he goes into the woods looking for something more. I'll take the happy route that involves

material success. Thank you. I think it's quicker in some ways. You know, one of your uh insights is it's

far easier to achieve our material desires than it is to renounce them. And uh

it depends on the person, but I I think you have to try that path. If you want something, go get it. Uh, you know, like

I I I quipped that the reason to win the game is to be free of it. So, you you play the games, you win the games, and

then you get hopefully you get bored of the games. You don't want to just keep looping on the same game over and over.

Although a lot of these games are very enticing and have many levels and are relatively open-ended.

Uh, and then you become free of the game uh in a sense that you're no longer trying to win it. You know, you can win

it. Uh, and either you move to a different game or you play the game for the sheer joy of it.

Yeah. You, another one of yours, most of the gains in life come from suffering in the short term so you can get paid in

the long term. I think that's classic. Winning the marshmallow test on a daily

basis. But, uh, there's an interesting challenge where I think people need to avoid becoming uh, a suffering addict.

Sort of using suffering as the proxy for progress as opposed to the outcome of the suffering. Right? It's like I was in

pain not eating the marshmallow. I was in pain doing this work. I have attached well-being and satisfaction to pain, not

to what the pain gets me on the other side of it. If you define pain as physical pain, then it's a real thing.

It happens and you can't ignore it. But that's not what we mean by suffering. Suffering is mostly mental anguish and

mental pain. And it just means you don't want to do the task at hand. Uh if you were fine doing the task at hand, then

you wouldn't be suffering. And then the question is what's more effective to suffer along the way or just to

interpret it in a way that it's not suffering? You hear from a lot of successful people

they look back and they say oh the journey was the fun part right that was actually the entertaining part and I

should have enjoyed it more. It's a common regret. Uh there's a little thought exercise I like to do,

which is you can go back into your own life and uh try to put yourself in the exact position you were in 5 years ago,

10 years ago, 15 years ago, 20 years ago. And you try to remember, okay, who was I with? What was I doing? What was I

feeling? What were my emotions? What were my objectives? And really, really try to transport yourself back and see

if there's any advice you'd give yourself. Anything you do differently. Now, you don't have new information. And

don't pretend you could have gone back and, you know, bought a stock or bought bought Bitcoin or whatever, but just

knowing what you know now in terms of your temperament and a little bit of age related experience,

how would you have done things differently? And I think it's a worthwhile exercise to do. So don't let

me rob you of the conclusion, but I'll tell you for me uh I would have done everything the same

except I would have done it with less anger, less emotion, less internal suffering because that was optional. It

wasn't necessary. And I would argue that someone who can do the job uh at least peacefully but

maybe happily is going to be more effective than someone who has unnecessary emotional turmoil.

Well, you end up with a series of miserable successes, right? The outcome may have been the same, but the entire

experience of getting there and and the journey is not only the reward. The journey is the only thing

there is. You know, even success, it's human nature to bank it very very quickly, right? Because the normal loop

that we run through is you sit around, you're bored, then you want something, then when you want something, you decide

you're not going to be happy until you get that thing. Then you start your bout of suffering or anticipation while you

strive to get that thing. If you get that thing, then you get used to it and then you get bored again. Then a few

months later, you want something else. And if you don't get it, then you're unhappy for a bit and then you get over

it and then you want something else. Right? That's the normal cycle. So whether you're happy or unhappy at the

end, it tends not to last. Now I don't want to be glib and say that oh there's no point in making money or being

successful. There absolutely is. Money solves all your money problems. So it is good to have money. Um that said there

are those uh those stories. I I don't know if you've seen those studies. I don't know how real these are. A lot of

these psych studies don't replicate, but it's a fun fun little study that shows that uh people who break their back and

people who win the lottery are back to their baseline happiness two years later. Yep. Again, I don't know if

that's entirely true. I think money can buy you happiness if you earned it because then along the way you have both

pride and confidence in yourself and you have a sense of accomplishment and you you know set out to do something and you

were right. So I I'll bet that lingers and then as I said money solves your money problem. So I don't want to be too

glib about it but I would say in general this this loop that we run through um of desire, dopamine, fulfillment,

unfulfillment like you you have to enjoy the journey. The journey is all there is, right? 99% of your time is spent on

the journey. So, what kind of a journey is it if you're not going to enjoy it? How do you shortcut that desire

contract? You could focus, you could decide that I don't want most things. I think we have

a lot of unnecessary desires that we just pick up everywhere. We have opinions on everything, judgments and

everything. Uh so, I think just knowing that those are the source of unhappiness uh will make you be choosy about your

desires. And frankly, if you want to be successful, you have to be choosy about your desires. You have to focus.

You can't be great at everything. You can't be great at everything. You're just going to waste your energy and

waste your time. Is fame a worthwhile goal? Uh, it gets you invited to better

parties, gets you into better restaurants. Uh, fame. So, fa fame is this funny thing

where a lot of people know you, but you don't know them. And, uh, it does get you put on a pedestal. Uh, it can get

you what you want, uh, at a at a distance. So, I wouldn't say it's worthless. Obviously, people want it for

a reason. Um, it's high status, so it attracts the opposite sex. Uh, especially for men, it attracts women.

Uh, that said, it is high cost. It means you have no privacy. Um, you do have weirdos and lunatics. Uh, you do get hit

up a lot for weird things. Uh, and you're on a stage, so you're forced to perform, so you're forced to be

consistent with your past proclamations and actions, and you're going to have haters and all that nonsense. But the

fact that we do it, the fact that we all seem to want it means that it would be disingenuous to say, "Oh, no, no, I'm

famous." But you don't want to be famous. Um, that said, I think fame, like

anything else, is best produced as a or pursued as a byproduct of something potentially more worthwhile. Um, wanting

to be famous and craving to be famous and being famous for being famous, these are sort of traps.

Fame for fame's sake. Yeah. Exactly. So, it's better that it's earned fame. Uh so for example earn

respect in the tribe is you do things that are good for the tribe. Uh who are the most famous people in human history?

Uh there uh you know there there are people who sort of transcended the self. The Buddhas and the Jesuses and the

Muhammads of the world. Who else is famous? Uh the artists are famous. You know art lasts for a long time. The

scientists are famous. They discover things. The conquerors are famous presumably because they conquered for

their tribe. There was someone that they were fighting for. So generally the higher up you rise by doing things for

greater and greater groups of people even though it may be considered tyrannical or negative like uh you know

Jenghaskhan is famous but uh to the Mongols he was doing good to the rest of them not so much uh

the higher level you're operating at the more people you're taking care of the more you sort of earn respect and fame

and I think those are good reasons to be famous if if if fame is empty if you're famous just cuz your name showed up in a

lot of places or your face showed up in a lot of places then that's a hollow fame and I think deep down you will know

that and so it'll be fragile and you'll always be afraid of losing it and then you'll be forced to perform

so the kind of fame that uh pure actors and celebrities have I wouldn't want but the kind of fame that's earned because

you did something useful uh why dodge that now you can there's a challenge I think especially if people

make uh very loud public proclamations about things you mentioned there about um you're almost hostage to the things

that you used to say that um being able to update your opinions and change your mind looks very similar to the internet

as hypocrisy does. No, no, no. The difference between me saying something in the past and saying something

different now is perhaps I've learned, perhaps I've updated my beliefs, but so few people do it in a legitimate way. I

think that the grifter shill you see this is the the the smoking gun that shows that he didn't really believe that

thing all along. Right. And uh yeah, I I went to a retreat in LA a couple of years ago and there was a

guy that I used to follow that a big um business and productivity advice content creator really really successful and he

just totally stepped back from everything and went uh like monk mode and focused on his business. I asked him

why and he said uh I started feeling like I had to live up to in private the things that I was saying in public.

Right. Yeah. It's a it's a what was it that uh who said it was a mein that um foolish

consistency is a hobgoblin of little minds right um but essentially look all life is all learning is error correction

right every knowledge creation system works through correcting errors making guesses and correcting errors so by

definition if you're learning you're going to be wrong most of the time and you'll be updating your priors and so

for example I did this Joe Rogan podcast I don't know it's like eight or nine years ago um and people will call out

like the one thing that didn't turn out to be correct, right? And it's just like and they just beat on it because it it

helps them in their mind raise their status a little bit. Aha, I caught him in an error. Well, I think if you catch

someone in a blatant lie where there's believe one thing and they say another, that's legit. That's a character flaw.

They shouldn't be lying. But on the other hand, if they just made a guess at something and they got it wrong. And by

the way, mostly it's about the AI AGI thing. And I think I'm still right about that, but it's a different story. Um

people who think we have achieved AGI just fail a touring test from their side. Um but uh

it's funny how people latch on to single proclamations. But the reality is all of us are dynamical systems. We're always

changing. We're always learning. We're always growing. And uh hopefully we're correcting errors. What you don't want

to be doing is lying in public so that because you're you're trying to look good. And I think people can smell that.

I I I what this world really lacks right now is authenticity and because everybody wants something. They want to

be seen as something. They want to be something that they're not. And so you do catch a lot of people uh saying

things that they don't really believe. And I think people are very sensitive to that.

Uh [ __ ] radars have become hypers sensitized to try and work out whether or not this person means the thing that

they're saying. Yeah. I mean they they a lot of people are wrong. Most of us are wrong most of

the time especially in any new endeavor. Difference between being wrong and disingenuous though, purposefully wrong.

Correct. Exactly. So I think I think that's the big difference. If someone is wrong, no big deal. As long as they have

a genuine reason for saying what they're saying, or believing what they're believing. But if they are lying to

elevate their status or their appearance or to live up to some expectation, that's the mistake. And that's a mistake

not just for the listener, it's a mistake for themselves cuz then you're going to get trapped in a hall of

mirrors. You yourself are going to be consistent with your past proclamations. So if you're lying to others, you're

going to be lying to yourself. You're puppeted by a person that you are not even.

That's right. Yeah. It's it's like what was that line? There's you're you're basically trying to impress people who

you know don't care about you. Um so they don't like the real you and if they saw the real you they wouldn't care and

the people who would like the real you don't get to see the real you so they pass you by

right? You only want the respect of the very very few people that you respect. Uh trying to demand respect from the

masses is a fool's errand. status games, the allure of acrewing, whether it's fame, actual fame, or just

the competition comparison trap, it's always there. Uh there's a real draw of being swayed by social approval. How

should people learn to get less distracted by status games in that way? I think it it just helps to see that

status games don't matter as much as they used to. uh in old society, let's go back hunter gatherer times, there was

no such thing as wealth. You just had what you could carry. Um there was no stored wealth. So wealth games didn't

really exist to wealth creation games. All that existed was status games. If you were high status, then you got what

little was available first. Um but even back then, you had to earn your status by taking care of the tribe. Uh now we

have wealth creation where you can actually create a product or a service. you can scale that product or service

and you can provide abundance for a lot of people. Uh and that's not zero sum, that's a positive sum game. I can be

wealthy, you can be wealthy, we can create things together and clearly since we are all collectively far far

wealthier than we were in huntergatherer times. Uh wealth creation is positive but status is limited. There's limited

status to go around. It's a ranking ladder. It's a hierarchy. And so it's a rise in status. Somebody else has a

lower in status. Now you can have multiple kinds of status. So you can expand some kinds of status, but it's

not like wealth creation where it can go infinitely where we can all be, you know, living in the stars and moon bases

or Mars colonies or what have you. So just realize that status games are inherently limited. Uh they're always

combative. Um they always require uh direct combat whereas uh wealth creation games can be just you're creating

products. You don't have to fight anybody else. Yes, in the marketplace your product has to succeed, but that's

not quite the same as uh invective against other people or being angry with other people or feeling pushed down or

pushed up or having a beef with somebody. So, I would argue that wealth creation

games are both more pleasant. Uh they're positive sum and they actually have uh concrete material returns. If you have

more money, you can buy more. Show me where you can exchange your status at the bank.

Exactly. Yeah. It's it's it's vague and it's fuzzy. Now, you see people get rich, they have money, what do they

want? They want status. So they go to Hollywood, start starring in movies, they donate to nonprofits, they go to KS

or Davos or what have you. Um, and they start trying to trade the money for status. So, you know, people always want

what they don't have. Uh, and we are evolutionarily hardwired for status because as I said, wealth creation

didn't really exist until the agricultural revolution, uh, when you could store grain and then the

industrial revolution took it to another level and now the information age is taking it to yet another level.

But there's never been an easier time to make money. Yes, it's still hard, but there's never been an easier time to

create wealth because there's so much leverage out there. There's so much opportunity. You still have to go find

it. It's not easy. It's not going to fall on your lap, and you have to learn something and know something and do

something interesting. But nevertheless, it's possible to many more people. A few hundred years ago, you were born a

surf, you were going to die a surf. There was almost no way out of that. That's changed. And so I would argue

that you're better off focusing on wealth games and status games. If you're trying to um build up, for example, your

following on a social network and get famous and then get rich off of being famous, that's a much harder path than

getting rich first. Um and then go for your fame afterwards would be my advice.

Well, a lot of people do that as you said. It's funny how uh people who have achieved such a level of wealth that you

don't think why do you need the status given that most people use status to then try and cash in to achieve wealth

if you've achieved [ __ ] money already if you're post money or uh asset heavy as it's known. Um why are you trying to

go in the other direction? Well, as you said because we've we've got an illustrious history biologically of

wanting status and wealth is kind of novel. It's new. It's new. Wealth is uh

something that you have to understand more intellectually. Yeah, there's a physical component, more food, more

survival, but uh to truly understand the effects and the powers and the abilities and limitations uh and the advantages

and disadvantages of wealth, you have to use your neoortex a lot more. Does that mean

it's not limbic? The reason to play the game is to win the game and be done with it is harder

to win and be done with for status than it is for wealth. That's a good observation. I had thought

that through, but you're right. Yeah, I think that's right. I think you people will always want more status. Uh but I

think you can be satisfied at a certain level of wealth. Well, as well you always have this sort of sense. This

is what leaderboards are, right? This is the the billboard chart, right? And it is zero sum and it is

I guess you know the Forbes richest people on the planet thing. That one's harder to climb the ladder

on. But uh the fact that for example iTunes and YouTube can put you in competition against your contemporaries

every single day and make you go up and down and show you likes and comments and ratings. This is how much you're up.

Exactly. They they keep you running on that treadmill forever. Jimmy Carr has this cool idea where he

says trajectory is more important than position. So if you are number 101 in the world

but last year you were number 200 versus you're number two in the world but last year you were number one. there is this

sense of the deceleration is very very tangible and um it's again it goes back to evolution you know

something that is bleeding eventually dies unless you stop the bleeding so you're you're hardwired not to lose what

you have and because we evolve in conditions where we're so close to just not surviving uh you don't want to give

anything up. It's hardwired into us to not give anything up. So you grip tightly.

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outcome in the world is not having self-esteem. Why? Yeah, that's a tough one. Uh, well,

I I I look at the people and I don't want to offend anybody, but I look at the people who don't like themselves,

and that's the toughest slot because they're always wrestling with themselves, and it's hard enough to face

the outside world. Um, and no one's going to like you more than you like yourself. So, if you're struggling with

yourself, then the outside world becomes an insurmountable challenge. And it's hard to say why people have low

self-esteem. It might be genetic. It might just be circumstantial. A lot of times I think it's cuz they just weren't

unconditionally loved as a child and that sort of seeps in at a deep core level. Um but self-esteem issues can be

the most limiting. Uh one interesting thought is that you know to some extent self-esteem is a reputation you have

with yourself. Um you're watching yourself at all times. You know what you're doing and you have your own moral

code. Everyone has a different moral code. But if you don't live up to your own moral code, the same code that you

hold others to, uh it will damage your self-esteem. So perhaps one way to build up your self-esteem is to live up to

your own code very rigorously. Have one and then live up to it. Uh another way to raise your self-esteem might be to do

things for others. Uh if I look back on my life and you know what are the moments that I'm actually proud of,

there's very far and few between and it's not that often and it's not the things you would expect. It's not the

material success. It's not having learned this thing or that. It's when I made a sacrifice for somebody or

something that I loved. And uh that's when I'm actually ironically most proud. Now that's through an explicit mental

exercise. But I'll bet you at some level I'm recording that implicitly. So that tells me that even if I am not being

loved and the way to create love is to give love to to express love through sacrifice and through duty.

And so I think doing things like that can build up your self-esteem really fast. It's interesting when you talk

about sacrifice because a lot of the time people say, "I sacrificed so much for my job." It's like, "Yeah, but that

was you sacrificing something that you wanted less for something that you wanted more as opposed to genuinely

taking some sort of cost." And uh yeah, I wonder whether if self-esteem is you adhering to your internal your your

actions and your values aligning um even when it's difficult or perhaps even more so when it's difficult. I wonder whether

there is a price that people who are more introspective, high integrity pay because you think well you've got this

uh heavy set of overheads that you need to pay in some way.

Well, if being ethical were profitable, everybody would do it, right? So, uh you at some level it does involve a

sacrifice. Uh but that sacrifice can also be thought of as you're thinking for the long term rather than the short

term. Um for example the virtues are the set of uh virtues a set of beliefs that if everybody in society followed them as

individuals it would lead to win-win outcomes for everybody. So if I am honest and you are honest then we can do

business more easily. We can interact more easily because we can trust each other. So even though there might be a

few liars in the system as long as there aren't too many liars and too many cheaters uh a high trust society where

everybody's honest is better off. And I think a lot of the virtues work this way right? If I don't go around sleeping

with your wife and you don't sleep with mine and you know if I don't take all the food that's at the table first and

so on, then we all get along better and we can play win-win games. Uh in game theory, the most famous game is

prisoners dilemma. But that's all about everybody cheating and the Nash equilibrium. The stable equilibrium

there is everybody cheats and you're for the only way you can be you can play a win-win game is if you have long-term

iterated moves. But that's not actually the most common game played in society. The most common game played as one

called a stags hunt where if we cooperate, we can bring down a big stag and both have big dinners, but if we

don't cooperate, then we have to go hunt like rabbits and we each have small dinners.

So most of uh and and that game has two stable equilibriums. And one could be where we're both hunting the rabbit and

one could be where we're hunting the stag. So the high trust society is a more most more virtuous society where I

can trust you to come hunt the stag with me and show up on time and do the work and divide it up properly. So you want

to live in a system where everybody has their own set of virtues and follows them and then we all win. But I would

argue you don't need to do that for sacrifice. You don't need to do that for other people. You can do it just purely

for yourself. You will have higher self-esteem. You will attract other high virtue people.

Would I go on a stag hunt with me? Correct. Yeah, that's right. And if you're the kind of person, if you're the

kind of person who long-term signals ethics and virtues, then you will attract other people who are ethical and

virtuous. Whereas, if you are a shark, you will eventually find yourself swimming entirely amongst sharks. And

that's an unpleasant existence. But again, this goes back to the equivalent of the marshmallow test. And by the way,

the marshmallow test does not replicate. I saw it replication crisis hard recently.

But it is about trading off the short term for the long term. Uh, and so I think for a lot of these so-called

virtues, there are long-term selfish reasons to be virtuous. Yeah. Uh, did you deal with self-doubt

in the past? Is that something that was a hurdle for you to overcome? Yes and no. I think I I dealt with

self-doubt in the sense that, oh, I don't know what I'm doing and I need to figure it out. Um, but I didn't doubt

myself in the way of somebody else knows better than me for me or that, you know, I'm an idiot or I'm not worthwhile or

anything that I I guess I had the benefit of I grew up with a lot of love like the people around me love me

unconditionally. And so that just gave me a lot of confidence. Uh, not the kind of confidence that would say I have the

answer, but the kind of confidence that I will figure it out and I know what I want or only I am a good arbiter of what

I want. Yeah. That level of self-belief, I suppose, allows you to determine what is

it that matters to me, my self-esteem, should I chase this thing or not? I can make a fair judgment on that as opposed

to being so swayed. But it's such a good point about even if you think you're not consciously logging the stuff that

you're doing, there is some that's in the back of your mind. Was it the Damon? Is that what the ancient Greeks or

something used to talk about? Yeah. The Yeah. Also in computer science like there's a concept of a demon which

is a uh a program that's always running in the background. You can't see it. Okay.

Um but yeah, it probably comes from the ancient Greek demon. Uh but yeah, I what you know that you don't even know you

know is far greater than what you know you know, right? You can't even articulate most of the things you know.

There are feelings you have that have no words for them. There are thoughts you have that are felt within the body or

subconsciously that you never articulate to yourself. You don't really you can't articulate the rules of grammar yet you

exercise them effortlessly when you speak. So I would argue that your implicit knowledge and your knowledge

that is unknown to yourself is far greater than the knowledge you can articulate and that you can communicate.

And so at some level you're always watching yourself. That's what your consciousness

is, right? It's the thing that's watching everything including your mind, including your body. M

so if you want to uh have high self-esteem then earn your own selfrespect.

I had this idea the internal golden rule. So the golden rule says treat others the way that you should be

treated. You want to be treated. The internal golden rule says treat yourself like others should have treated you

and it was a a repost to maybe people that didn't grow up with unconditional love. Yeah.

In that way. On the love thing, one of the interesting things about love is you can try to remember the feeling of being

loved. So go back to when someone was in love with you or someone did love you and like really remember that feeling

like really sit with it and try to recreate it within yourself and then go to the feeling of you loving someone and

when you were in love. And I'm not even talking about romantic love necessarily. So be a little careful there. I'm

talking more about like love for it can sometimes get complex if you're talking about past romantic love,

right? a sibling or a child or something like that or or a parent and uh think about when you felt love towards someone

or something. And now which is better? And I would argue that the feeling of being in love is actually more

exhilarating than the feeling of being loved. Being loved is a little clawing. It's a little too sweet. You kind of

want to push the person away. It's a little embarrassing. And you know that if that person is too much into it that

you feel constrained. On the other hand, the feeling of being in love is very expansive. It's very open. It actually

makes you a better version of yourself. It makes you want to be a better person. And so you can create love anytime you

want. It's just that craving to receive it. That's the problem. The most expensive trait is pride. How

come? Oh, that was a recent one. Uh I I tweeted that just because I think that

uh pride is the enemy of learning. So when I look at my friends and colleagues, the ones who are still stuck

in the past and have grown the least are the ones who were the proudest because they sort of feel like they already had

the answers. And so they don't want to correct themselves publicly. And so this goes back to the fame conversation. You

get locked into something you said. It made you famous. You're known for that. And now you want to pivot or change.

So pride prevents you from saying I'm wrong. It What's pride in this context here?

It could be as simple as you're trading stocks and then you don't admit you were wrong. So you hang on to a lousy trait.

Uh it could be that you uh made a decision to uh you know marry someone or move somewhere or enter a profession, it

doesn't work out and then you don't want to admit that you were wrong so you get stuck in it. Uh it's mostly about

getting trapped in local maxima as opposed to going back down and climbing up the mountain again.

Mhm. And that's why it's an expensive trade because you continue to need to repay it in one form or another.

Yeah. You're you're just stuck at a suboptimal point. Uh it's going to cost you money. it's going to cost you

success and time and time. Uh the great artists always

have this ability to start over whether it's Paul Simon or Madonna or you two and I'm dating myself a little bit. Um

but even the great entrepreneurs, they're just always willing to start over. Uh I'm always struck by the Elon

Musk story where, you know, he uh he did PayPal as X.com originally. Actually, it was his his financial institution that

got merged into PayPal. It's good that you've got the domain. You know what I mean?

Yeah, exactly. I'll park that. I'll hold on. He's consistent. He's been using it for

quite a while. Um, and he said something like along the lines of, uh, I made $200 million from the sale of PayPal. I put

$100 million into SpaceX, 80 million Tesla, 20 into Solar City, and I had to borrow money for rent. Right? This guy

is a perennial risk taker. He's always willing to start over. He doesn't have any pride about being seen as successful

or being seen as a failure. He's willing to put it all in. Back himself again each time.

Back himself again each time. But the key thing is he's always willing to start over, right? even now when he's

sort of made his his new startup is a USA, right? He's basically trying to fix it like he would fix one of his

startups. And I think that is a willingness to look like a fool and that is a willingness to start over. And a

lot of people just don't have that. They become successful or they become rich or they become famous and that's it.

They're stuck. They don't want to go back to zero. And creating anything great requires zero to one. And that

means you go back to zero and that's really painful and hard to do. Talking about risk, something I've been thinking

about a lot to do with you. Any moment when you're not having a good time, when you're not really happy, you're not

doing anyone any favors. I think lots of people have become unusually familiar with suffering

silently in that sort of a way of not having a high bar for your expectation for

quality of life. Uh yeah, a lot of it is just you're memeing yourself into a bad outcome because you think that somehow

suffering is glorious or that it makes you a better person or you know my old quip was if you're so smart why aren't

you happy? Why can't you figure that one out? Um the reality is you can be smart and happy. There are plenty of people in

human history who are smart and happy. Uh and I think it just starts with saying yeah you know what I'm I'm going

to be happy. There was a guy that I met in Thailand a long time ago and uh he used to work for Tony Robbins. uh you

know he had a great attitude and uh we were sitting around and he said you know uh he said I realized one day that

someone out there had to be the happiest person in the world like there just that person just has to exist he said why not

me I'll take on that burden I'll be that guy and I heard that I was like wow that's pretty good that's a good frame

right he knew how to reframe things and so I think a lot of happiness is just a choice uh in the sense that you

make first you just identify yourself as actually I'm going be a person that's going to be happy. I'm going to figure

it out. And you just figure it out along the way. You're not going to lose your other predilictions. You're not going to

lose your ambition or your desire for success. I think a lot of people have this fear that, oh, if I'm happy, then I

won't want to be successful. No, you'll just want to do things that are more aligned with the happy version of you,

and you'll be successful at those things. And believe me, the happy version of you is not going to look back

at the unhappy version and say, "Oh man, that that guy was going to be more success. I wish I was him."

You're actually trying to be successful so you'll be happy. That's the whole point. you have you've gotten it

backwards. You you unlocked one of my trap cards. Um, one of my favorite insights is that

we sacrifice the thing we want for the thing that's supposed to get it. So, we sacrifice happiness in order to

be successful so that when we're finally sufficiently successful, we can actually be happy. And if you have some sort of

simultaneous equation and you just sort of stripped success off from both sides, the at least in my own life, I have not

found there to be a trade-off. If anything, I have found that the happier I get, the more I am going to do the

things that I'm good at and aligned with and that will make me even happier. And so, I actually end up more successful,

not less. The aligned with thing is interesting. Uh, I'm going to try and put this across as delicately as I can.

I would say from the bit of time that we'd spent together, you have a really interesting trait of

holistic selfishness. Uh, you're sort of prepared to put yourself first. um you seem largely unfazed by saying or doing

things that might might result in other people feeling a little bit awkward if it's truthful for you. Uh it's like

unapologetically self-prioritizing, I guess. Yeah, I think everybody is. Uh maybe unapologetic is the part that's

that's relatively uh rare, but I think everybody puts themselves first. That's just human nature. You're you're here

because you survive. You're a separate organism. That's interesting. I'm maybe. But I

know we like to virtue signal and pretend we're doing it for each other. How many how many times does somebody

say, "Yeah, of course. I'd love to come to the wedding." They're like, "I don't want to be at the [ __ ] wedding." How

many times does someone say, "How are you doing today?" And they don't tell you. How many

I don't go to weddings. But this is my point. So I don't think you're necessarily

right with that. I think that people do I don't think they put themselves first. I sometimes think that they they

compromise what it is that they want in order to appease socially what's in front of them.

Yeah. I just view it as you're wast everyone's wasting their time on it. Um, don't do something you don't want to do.

Why Why are you wasting your time? There's so little time on this earth. Life goes fast. What is it? 4,000 weeks.

That's your lifespan. Um, and and yes, we hear that, but we don't remember it. But, uh, I guess I'm keenly aware of how

little time I have, so I'm just not going to waste it. How have you got more comfortable at um,

being the unapologetic self- prioritizer? Yeah, I've gotten I've gotten utterly

more and more ruthless on it. Ma mainly it's that I see or hear people's freedom and then that liberates me further. So I

read a uh I read a blog post by uh P Mark aka Mark Andre where he said don't keep a schedule and I took that to

heart. So I deleted my calendar and I don't keep a schedule. I try to remember it all in my head. If I can't remember

it, I'm not going to add I'm glad you got here on time. Yeah, exactly. Um

I hate to look things up at the last minute. Mhm. Uh so, but ironically, I don't even know

if Mark himself follows that, but he made the correct point. Uh I read a little story about Jack Dorsey doing all

his business off his uh iPhone and iPad and not even going into a Mac, and I said, "Okay, I want to do that." So, I'm

going to operate through text messaging and not put up my nasty email. Does that feel like more freedom?

It does. Yeah. Cuz you're on the go. Um so, I have a nasty email autoresponder that says, "I don't check email and

don't text me either." Right. If you need to find me, you'll find me. Obviously, some of this is a luxury of

success, but some of these habits I adopted long before actually the hostile email autoresponder started a long time

ago. Um, I used to own the domain. I let it go. I don't do coffee.com. I used to reply from that email uh just so people

would get the point. But I stopped being rude about it. Now I just ghost. I just disappear. Um, my wife knows not to ever

uh book or schedule me for anything. Uh, I'm not expect I'm not expected to go to couples dinners. I'm not expect to go to

birthdays. I'm not expect to go to weddings. If somebody tries to rope her into having me show up, she says he

makes his own decisions. You got to ask him directly. What about vice

versa? Well, are you not killing serendipity in a way that No, no. I'm freeing up all my time. So,

my entire life is serendipity. I get to interact with whoever I want, whenever I want, wherever.

You'll hear the invite, but make the decision because if you're if there's fewer things in coming, you're assuming

that you know what's best for you to anything in the future. So, I'll say, "Okay, if that thing is interesting,

I'll see if I can get in that day when I'm in the mood." But there's nothing worse than something coming up that your

past self committed you to that your present self doesn't want to do. God damn it.

Past. Yeah. And then it destroys your entire calendar. It destroys your your day because there's like, oh, this 1

hour slot which is sitting like a turd on my calendar that I have to like schedule my whole day around. I can't do

anything the 20 minutes before, the 20 minutes afterwards. Even for phone calls, if someone wants

to do a phone call, say, "Okay, just text me when you're free. I'll text you when I'm free." and we'll just do it on

the fly. It's a much better way of living than this overly scheduled uh you know cal.com or iical whatever.

The uh the overscheduled life is not worth living. It's not. I think it's a terrible way to

live life. That's not how we evolved. It's not how we grew up. Um it's not how how we were as children hopefully uh

unless you're a helicopter parent or a tiger mom. Um

your natural order is freedom. Uh I had a friend who uh said to me once, you know, uh I never want to have to be at a

specific place at a specific time. And I was like, "Oh my god, that's freedom." When I heard that, that changed my life

right there. You still arm alarm clockless? Yes, I'm alarm clockless. Today, I did

set my alarm clock just so I wouldn't miss this. Very important. Yeah. If you still,

but just so you know, I set the alarm clock from 11:00 a.m. in case I was stricken with a flu that day. I wasn't

going to set my alarm clock for 8:00 a.m. or 9:00 a.m. And sure enough, I got up many hours before that.

Um, but it was sort of a backup emergency alarm. In fact, sometimes when I something

that I need to do, I don't want to look at a calendar, so I'll just set an alarm for it.

Just sink a little bit more into that like kind of that [ __ ] you energy, that self- prioritizing energy because I

think people rationally love the idea of this. I'm going to do what only I want to do. uh even if they've got the level

of freedom, it's not [ __ ] you energy in the sense that I think everyone should live their

life that way to the greatest extent possible. Obviously, we have our requirements around work and obligations

that are genuinely important to us. But don't fritter away your life on randomly scheduled things and things that aren't

important don't matter and events and weddings and you know tedious dinners with tedious people that you don't want

to go to. To the extent you can bring freedom into your life, optimize for that, you'll actually be more

productive. You won't just be happier and more free. You will be more productive because then you can focus on

what is in front of you, whatever the biggest problem of that day. When I wake up in the morning, uh the first 4 hours

are when I have the most energy and that's when I want to solve all the hard problems. And the next 4 hours are when

I kind of want to, you know, do some more outdoorsy activities or I want to work out or maybe I can, you know, have

some meetings, but I'll try to do those last second based on whatever the day's priorities demand. the last 4 hours I

kind of want to wind down. I want to hang out with the kids and I want to play games or read a book or something

like that. So having that flexibility and freedom is really important. So you can just put

whatever is most needed into the slot at that moment. Uh and instead if I have like a meeting at 2 p.m. and then I have

to like get a thing and some emails done, I put that off till 6 p.m. I'm rushing. I'm not going to be productive.

I'm not going to be uh You're certainly not free. You're not I'm definitely not free. But

also another thing that I really believe is that inspiration is perishable. Act on it immediately. So when you're

inspired to do something, do that thing. If I'm inspired to write a blog post, I want to do it at that moment. If I'm

inspired to send a tweet, I want to do it at that moment. If I'm inspired to solve a problem, I do it that moment. If

I'm inspired to read a book, I want to read it right then. If I'm inspired to solve a problem, I solve it right there.

If I want to learn something, I I do it at the moment of curiosity. The moment the curiosity arrives, I go learn that

thing immediately. I download the book. I get on Google. I get on ChatGpt, whatever. I will figure that thing out

on the spot and that's when the learning happens. It doesn't happen because I've scheduled time because I've set an hour

aside because when that time arrives I might be in a different mood. I might just want to do something different.

So I think that spontaneity is really important. You're going to learn best when you're having fun when you

generally are enjoying the process not when you're forced to sit there and do it. How much do you remember from

school? You know you were forced to learn geography, history, mathematics on this schedule at this time according to

this person. Didn't happen. All the stuff that sticks with you is you learned it when you wanted to, when you

genuinely had the desire. And that freedom, that ability to act on something the moment you want to is so

liberating that most of us go through our lives with very very little tastes of that. If you live your entire life

that way, that is a recipe for happiness. It feels like efficiency that that you

have efficient also. You have the inspiration that is going

to be the most frictionless time to ever do that particular task. So, oh, I've had the inspiration to do that. I'll put

that off until a time when I no longer really want to do it quite so much. And while I do want to do that thing, I'll

do something else that I needed to do because it's on the schedule. It does not work. Procrastination is

because you don't want to do that thing right now. You want to do something else. Go do that something else. I

reject this frame that efficiency and productivity and success are counter to happiness and freedom. They actually go

together. How so? The happier you are, the more you can

sustain doing something, the more likely you're going to do something that will in turn make you even happier. and

you'll continue to do it and you'll outwork everybody else. The more free you are, the better you can allocate

your time and the less you're caught up in a web of obligations and commitments and the more you can focus on the task

at hand. In other news, this episode is brought to you by Function. Staying on top of your health requires more than

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That's functionhealth.com/modernwisdism. This is related to another insight of yours. The less you want something, the

less you're thinking about it, the less you're obsessing over it, the more you're going to do it in a natural way,

the more you're going to do it for yourself, you're going to do it in a way that you're good at and you're going to

stick with it. The people around you will see the quality of your work is higher. But this seems like a difficult

tension to navigate because an obsessive attention to detail is a competitive advantage of your work as well. So you

have these two things sort of conflicting with each other. No one is going to beat you at being you if it So

one of the things I like to say is like find what feels like play to you but looks like work to others. So it looks

like work to them but to you it feels like play. It's not work. So you're going to out compete them because you're

doing it effortlessly. You're doing it for fun. They're doing it for work. They're doing it for some byproduct. To

you it's art. It's beauty. It's joy. It's it's flow. It's fulfilling. Uh, you must enjoy podcasting. If you didn't,

you wouldn't be good at it. You would either, right? If you would, you if if you decided that the right way to get

ahead in life was to go write books, you would nobody would have heard of you. Chris Williamson's book would be a

complete flop. That's not who you are. You're a podcaster. You enjoy talking to people. You enjoy interviewing them. The

more you do things that are natural to you, the less competition you have. You escape competition through authenticity.

by being your own self. If I had to summarize how to be successful in life in two words, I would just say

productize yourself. That's it. Just figure out what it is that you naturally do that the world might want that you

can scale up and turn into a product and it'll be it'll eventually be effortless for you. Yes, there's always work

required, but it won't even feel like work to you. It'll feel like play to you. And modern society gives us that

opportunity. You know, if you were 2,000 years ago, you're born in a farm. Your choices are very limited, right? You're

going to do stuff on that farm. Now, you can literally wake up and you can move to a different city. You can switch

careers. You can switch jobs. You can change the people that you're with. Uh, you know, you can change so many things

about who you are and who you're with and what you're doing that there is infinite opportunity out there for you.

Literally infinite. And so it's much better to treat this like a search function to find the people who need you

the most, to find the work that needs you the most, to find the place you're best suited to be at. And it's

worthwhile to spend time in that exploration before diving into exploitation. The biggest mistake in a

world with so many choices is premature commitment. If you prematurely commit to being a lawyer or a doctor and now

you've got like, you know, 5 years invested into that, you might have just completely missed. You might just end up

in the wrong profession, the wrong place, or the wrong people for 30 years of your life grinding away. And yes, the

best time to figure that out was before, but the second best time is now. So, just change it.

And also, presumably kill things that aren't working very quickly. By default, you should kill everything.

You know, if you can't decide, the answer is no. Uh, and most things you should just be saying no to. The part of

my keeping my calendar free is just by default saying no to everything. Do I want to create a calendar just to add

your event, right? Or to add your need or your desire. One of the other things about, you know, early on in life,

you're looking for opportunities. So, you're saying yes to everything. And that is a phase that you go through.

That is the exploration phase. Later, when you found the thing you want to work on, you're in the exploitation

phase. You have to say no to everything by default. And if you don't say no to everything by default, if you have to

even explicitly go out of your way to say no to something, that will take up time. Uh, for example, you know, there

there are a lot of people out there who are into hustle culture and and a big piece of hustle culture is like, well,

you're not going to get something if you don't ask for it. So, they'll hustle people. They'll always be sending you

requests, messages. Yeah, this is a famous person problem, but I have it. And people are always asking me for

things. And I kind of squirm when I get these messages, and I'm sure you get these two text messages, emails saying,

"Hey, Chris, my friend so and so should really be on your podcast, or you should come to my event. You should write a

forward for my book." And you kind of squirm when you get this, right? You have to figure out how to say no. And

one of the things I learned along the way is that if you wouldn't ask somebody else to do it and then you get that

request yourself, you can just dismiss it. You don't have to respond. You don't you don't even let let it enter your

brain. You have to be able to delete emails and text messages without flinching if you want to scale. And

scaling is very important. Scaling your time is really important. Every interruption will take you out of flow.

So the only way you can remain in flow is if you get either very good at ignoring these things by default or

closing yourself off like a hermit like our mutual friend Tim Ferris does or you just become emotionally capable of not

registering these as something that causes turbulence inside of you. That not registering it emotionally

thing is that uh it's fundamental. That's so fundamental to so many things in life.

Okay. Can we dig into that a little bit? is because again I've only seen you as you right I didn't know you 20 years ago

I didn't know you as a child um so I've only seen you with this holistic selfishness the in integrated

self- prioritization whatever we I don't know what we called it selfish is fine I'll take selfish I'm

selfish I'm very selfish person don't contact me uh yeah that emotional reaction I also

get the sense too that maybe people have lived obligation life for so long that they actually kind of

struggle to tap into what it is that they want. They've hidden their wants and their desires and their needs and

they've dep prioritized themselves so much for so long they go, "What do I want actually? What what is it? Do I

want to go to this thing or not?" Because all I've done is be [ __ ] puppeted, right? I've been marionetted

by other people's desires for so so so long. I can't even tap into that anymore. And saying no feels like a war

crime. So, so I think it's really good to be able to view your own mind and your own thoughts objectively and that

is the big benefit of meditation. It creates a small gap between your conscious observation self and your mind

and that lets you then look at your thoughts and evaluate them a little bit like you would a third party's

statements. And uh if you just take your mind to be you and they're integrated in one and the same at all times and you're

reacting from the mind, then you're not even going to question things that come into your mind. Anything that comes in

that creates a reaction will immediately create a reaction. But if you can observe your thoughts a little bit and

not in some woo way, but you can even just do it through therapy, you can do it through journaling, you can do it any

way you would like, you can just take long walks, you don't have to meditate and do lotus position. uh all that is

unnecessary. But if you can observe your own thoughts and view them a little objectively, then you can start being uh

a little more choosy, a little more critical and you can realize that there are no problems in the real world other

than maybe things that inflict pain on your body. Everything else has to become a problem in your mind first. You have

to view it and interpret it and create a narrative that it is a problem before it becomes a problem. And then you realize

that a lot of your emotional energy is spent on reacting to things that your mind is automatically saying are

problems. Uh and you don't need all those problems. Do you really need that many problems in your life? Again, I

would say try to focus on just one overarching problem and then go solve that problem. It's like if you want to

be successful, define success very concretely. Focus on that. In everything else, when it enters your mind, it

becomes a problem. Whether it's a judgment about the girl walking down the street or the car that just cut in front

of you or whether it's like you know this your accountant did this stupid thing like yes it's going to trigger you

but observe for a moment that like it's triggering me. I've created a problem. Do I really want to have this problem

right now? Do I want to spend the energy on this problem or do I want that going somewhere else? And it it doesn't have

to be that overt. You don't have to the mind mud wrestling with itself is also a problem but because it loves to do that.

I have my problems have got problems and I have a real problem about fixing my problems.

Yeah. Exactly. So you just you're going to be much happier and much more focused. Again, I think happiness and

focus and success can kind of complement each other. You're going to have much more energy. Just think about as mental

energy. You have much more mental energy to focus on the actual problems you want to solve if you don't start

unconsciously, subconsciously, reactively picking up problems everywhere. So before anything can be a

problem that takes up your emotional energy, you have to accept it as a problem. You can be choosy about your

problems. And I'm not saying I'm perfect in that regard, but I think I'm better than I used to be.

Well, lots of people are addicted to solving problems. So much so that sometimes people create problems when we

don't have any simply so that we can solve them. We have that going on. And then even worse is we take on problems

that we can't affect. So, uh, you know, another one of my little quips was, uh, you know, um, a rational person, uh,

can, uh, sort of a rational person should should cultivate indifference to things that are out of their control,

right? Uh, or a rational person can find peace by cultivating indifference to things that are out of their control.

Uh, and I'm as guilty as anybody of doom surfing on X or social media and getting worked up about things that I can't do

anything about, right? like, do I want to be fighting those battles in my mind when I literally cannot do anything

about it? So, if you find yourself looping on a problem, like you're watching the news too much and you're

getting caught up in a problem you can't do anything about, um, you have to step away from that. And, uh, modern media is

a delivery mechanism for mimetic viruses. And now, what's happened now is, you know, 100 years ago, 500 years

ago, if something wasn't happening in your immediate vicinity, you wouldn't hear about it. it wouldn't be a problem

for you. But now every single one of the world's problems has turned into a mimemetic virus which is going into the

battlefield of the news and is trying to infect your mind in real time so that yeah so that you become obsessed with

the war in Ukraine which is really far away or you get obsessed with climate change or you get obsessed with AI doom

or you get obsessed with whatever and there's nothing as riveting as the old religion the world is ending the world

is ending pay attention the world is ending and if you don't Cassandra complex at global scale

Cassandra complex at global scale Well, and I would argue that large percentages of the population are essentially just

infected with these mimetic viruses that have taken over their brain and are causing them to do incredible girration

about things that probably aren't even true or are greatly exaggerated. But even to the extent they are true,

they're things that that person can do nothing about. And they should put their own house in order first. So, you know,

another little line I have for myself is your family is broken, but you're going to fix the world. Right? People are

running out there to try and fix the world when their own lives are a mess. Oh my god.

Right? And and I think it defies credibility if you can't fix your own life first. I'm not going to take you

seriously if you can't fix your own life. Like all these philosophers who, you know, seem like people you emulate

and so smart or like these brilliant celebrities and they go off and commit suicide. Well, you just kind of

invalidated your whole way of life. It's like that line of in No Country for All Men where the killer is waiting for

the protagonist and protagonist shows up and the killer says, "Well, you know, if your set of rules brought you here, then

what good are your rules?" I didn't work. Um I I I I am self I'm holistically selfish in in that I want

to be objectively successful in everything I set out to want. Mhm. Yeah. Uh you have one life. Don't

settle for mediocrity. Don't settle for mediocrity. And and I think the only like people debate

intelligence for example, right? We talk about IQ tests and all that, but I think the only true test of intelligence is if

you get what you want out of life. And there are two parts to that. One is getting what you want so you know how to

get it. And the second is wanting the right things. Knowing what to want in the first place. I could want to be a,

you know, 6'8 basketball player and I'm not going to get that. So it's wanting the wrong thing. So

that's wanting something that you can't get. That's wanting something you can't get.

Is also wanting something that you don't want. Yeah. Wanting something that's a booby

prize. There are plenty of booby prizes out there, too. Right. I haven't heard that word in about 20

years. Yeah. Prizes that are just not worth having or that create their own

problems. Well, if you're not careful, you can end up in a place in life not only that you don't want to be, but one

that you didn't even mean to get to. That's if you're kind of proceeding unconsciously. Uh but and usually I

think people end up there because they are uh going on autopilot with sort of societal expectations or other people's

expectations. So, uh you know, or out of guilt or out of like uh mimemetic desire. You know, Peter Teal has this

whole thing from Rene Gerard about how mimemetic desires are desires are picked up from other people. Uh, and some of

those are automatically baked into society like, you know, go to law school, go to med school, go to

whatever, go to business school. Um, or they might be from watching what your friends are doing and, you know, the

other monkeys are doing. Um, or it might just be, you know, what your parents expectations are. I might be a guilt.

You know, guilt is just society's voice speaking in your head, socially programmed, so you'll be a good little

monkey and do things that are good for the tribe. Um, but I think the the the best

outcomes come when you think it through for yourself and decide for yourself. And I don't think people spend enough

time deciding. For example, we run on these uh four-year cycles. You know, in Silicon Valley, you go join a startup,

you vest your stock over four years. That's the standard. Okay? Um uh in u uh college, you know, you go for four

years. High school, you go for four years. Um some things take longer. You know, you have children, they hit

puberty 9 years later. That's like a 9-year cycle until that relationship changes. Um but we're used to these

fairly long cycles, multi-year cycles in which we are committed to things. You go to law school, you know, four or five

year cycle. You go be a lawyer, 40-year cycle. These are very long cycles. The amount of time we spend deciding what to

do and who to do it with, very short, very very short, right? We spend, you know, 3 months deciding, one month

deciding on a job where we're going to be for 10 years or 5 years. And because a lot of discovery is path dependent

where the next thing you find on the path is depend on where you were on the previous path. You sort of start going

down this vector that is a very long distance. People decide frivolously which city to live in and that's going

to decide who their friends are, what their jobs are, their opportunity, their weather, their food supply, their air

supply, quality of life. You know, it's such an important decision, but people spend so little time thinking it

through. I would argue that if you're making a four-year decision, spend a year thinking it through. Like really

thinking it through. 25% of the time. Yeah. Exactly. There's the secretary

theorem. I don't know if you know that one. Computer science.

After you've done this many people, pick the best one of the next however many. That's right.

Yeah. The secretary theorem is this computer science professor is trying to figure out uh how much time he should

spend interviewing secretaries and then how long to keep the secretary. So let's say he's going to have a secretary for

10 years. Does he keep searching for you know one year, 2 years, 3 years, 1 month, 2 months? What is the optimal

time? Uh and it turns out that the optimal time is somewhere around a third. about a third of the way through,

you take the best person you've worked with and try to find someone that good or better. So that by the time you've

gotten about a third of the way through, you have, excuse me, seen enough that you now have a sense of what the bar is.

And then anybody who meets or exceeds that bar is good enough. And this applies to dating, this applies

to jobs and careers, this applies generally. But the interesting thing about the secretary theorem is that it's

actually not time based. It's not based on onethird of the time. It's iteration based.

The number of candidates, the number of shots you took on goal. That's right. So, you want to have lots

and lots of iterations. So, that means that you need to bail out quickly and you need to be decisive quickly.

That's right. You need to you need to take opportunities quickly and bail out

quickly. Correct. Like if you go back and you look through failed relationships, uh

probably the biggest regret will be staying in the relationship after you knew it was over.

Exactly. You should have left sooner. The moment you knew it wasn't going to work out, you should have moved on. So

in that sense, I think Malcolm Gladwell popularized this idea of 10,000 hours to mastery. I would say it's actually

10,000 iterations to mastery. It's not actually 10,000. It's some unknown number. But it's about the number of

iterations that drives a learning curve. And iteration is not repetition. Repetition is a different thing.

Repeating is doing the same thing over and over. Iteration is modifying it with a learning and then doing another

version of it. So that's error correction. So if you get 10,000 error corrections in anything, you will be an

expert at it. don't partner with cynics and pessimists. You mentioned there about uh the people who've got a

nightmare going on at home and are trying to fix the world. But a lot of the time that cynicism and pessimism we

find in ourselves. We see the world whether we want to whether it's because we've embied what the news or or the

negative people around us have said or it's a bit more kind of endogenous than that. It's just sort of in us. It's the

way that we see the world. How can people avoid cynicism and pessimism within

themselves? Yeah. Synism and pessimism is a tough one. It's we're naturally hardwired for

it. Again, I go back to evolution. I I'm sorry to keep harping on evolution, but within biology, there's very few good

explanatory theories. And you know, theory of evolution by natural selection is probably the best one. So, if you

can't explain something about life or psychology or human nature through evolution, then you probably don't have

a good theory for it. And I would say that pessimism is another one that comes out of this, which is in the natural

environment, you're hardwired to be pessimistic. Because let's say that I see something rustling in the woods and

if I move towards it and it turns out to be food and prey then good I get to eat one meal but if it turns out to be a

predator I get eaten and that's the end of that. So we are hardwired to avoid ruin um and and uh you know just dying.

So we are naturally hardwired to be pessimists but modern society is very different despite whatever problems you

may have with modern society. It is far far safer than living in the jungle and just trying to survive. uh and the

opportunities on the upside are nonlinear. For example, when you're investing, if you short a stock, you the

most money you can make is 2x. You just lose, you know, if the stock goes to zero, you double your money. But if the

stock is the next Nvidia and it goes 100x or a,000x, you make a lot of money. So upside through because of leverage is

nearly unlimited. Uh also in modern society, because there's so many different people you can

interact with, if you go on a date and it fails, there are infinite more people to go on a date with. In a tribal

system, there might have been 20 people and you can't even get through all of them. So, modern society is far more

forgiving of failure. And you just have to sort of neoccortically realize and override that. You have to realize that

you're much more running a search function to find the thing that'll work. And then that one thing will pay off in

massive compounding. Once you find your mate for the rest of your life, you find your wife or your husband, then you can

compound in that relationship. It's okay if you had 50 failed dates in between. The same way once you find the one

business you're meant to plow into and it'll compound returns. It's okay if you had 50 small failed ventures or 50 small

failed job interviews. It doesn't the number of failures doesn't matter. And so there's no point in being a

pessimist. It's you want to be an optimist. But I would say you want to be you want to be skeptical about specific

things. Every specific opportunity is probably a fail. But you want to be optimistic in the general. In the

general you want to be like something in here is going to work out. How do you navigate that tension?

I mean, exactly as I said, I'm optimistic in the general that if something fails right now, then this is

a little woowoo, but it wasn't meant to be. It was a learning experience. It was an iteration. As long as I learned

something from it, then it's a win. If I didn't learn from it, then it's a loss. But as long as you're learning and you

keep iterating fast and cutting your losses quickly, then when you find the right thing, you have to be optimistic

and compound into it. So, you don't want to jump into the first thing. And you don't want to marry the first person you

date necessarily, unless you got very lucky. Um, but you you want to investigate and

explore very very quickly until you find the match. And then you have to be willing to go all in. You have to be

willing to move your chips to the center of the table. So both those uh both those uh approaches are required.

So it's a barbell strategy. It's sort of black or it's white. And most people are sort of stuck in this gray bit. And I'm

like half in, but I'm kind of don't really know if I am. I also think like labels like pessimist, optimist, cynic,

introvert, extrovert, these are very self-limiting. Humans are very dynamic. There are times when you feel like being

introverted. There are times when you feel like being extroverted. There are contexts in which you'll be pessimistic.

There are contexts in which you'll be optimistic. Leave all those labels alone. It's

better just to look at the problem at hand. Look at reality the way it is. Try to take yourself out of the equation in

a in a sense. Like obviously you're involved, but motivated reasoning is the worst kind of reasoning. Uh you're not

going to find truth through highly motivated reasoning. You have to be objective. And objective means trying to

take yourself out of it as much as possible or at least your personality out of it as much as possible.

And so to the extent you run with this thick identity and personality, it's going to cloud your judgment. It's going

to try and lock you into the past. If you say, "I'm a depressed, unhappy person. Yeah, I'm going to be unhappy."

That's a way of locking yourself into your past. even saying, "I have trauma. I have PTSD." Yeah, you you feel

something. There are memories. There are flashes. There are occasional bad feelings. But don't define yourself by

it because then you'll lock it into your identity and you're just going to loop on it. It's better to stay flexible

because reality is always changing and you have to be able to adapt to it. Adaptation is also intelligence.

Adaptation is survival. Adaptation is kind of how you're here. You're here because you're an adapter and your

ancestors were adapters. So to adapt, you will be able to see things clearly. And if you're seeing them through your

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wisdom. [Laughter] Moving on to sort of thinking about

happiness. Obviously a topic of yours that's a it's honestly the one that I feel least

qualified to talk about. Is it like a guy that's got long arms teaching you how to bench press or a

dude that's really tall teaching you how to deadlift? someone that feels like they came from behind the eightball.

Yeah. Is you're you're asking a crazy person about their thoughts. So, just thought it through. Is happiness still

more about peace than it is about joy? It's just one of those overloaded words that means different things to different

people. So, I'm not even sure we're communicating the same language. But, uh what is happiness?

I think it's just basically being okay with where you are. Not wanting

not wanting things to be different than the way they are. Not having the sense that anything is missing in this moment.

Needing something to change. Your current positive situation being contingent on an adjustment

on getting something from the outside world. Ironically,

I think most people if you were to ask them when they were happiest for a sustained period of time, not for a

brief moment, because pleasure can override happiness and create kind of this illusion of happiness.

But if you ask people when they were happy for a sustained period of time, they were probably doing some variation

of nothing. That's interesting because in the chase is this sort of lack, this contingency.

That's right. But then you get bored. If you just sit around all the time, you get bored. So you want adventure, you

want surprise. Like there's a funny thought experiment of the bliss machine, right? Which is suppose I could drill a

hole in your head and put electrode in. And they did this with monkeys and I can put a wire in there and I can stimulate

just the right part of your brain and I can put you in bliss and you'll just be in bliss. Would you would you want that?

Would that be nice? For how long? Do it and I'll tell you.

Right. So most people will say, "Well, I don't want that. I want meaning. I don't want just bliss. I want meaning." And

you're like, "Okay, well, I'll put an electrode in there and I'll give you meaning. How about that?" And if you

kind of run this thought experiment long enough, I think most people realize actually what I want is I want surprise.

I want and I want the world to surprise me and I want to wrestle with it in ways that are

somewhat predictable but somewhat not. And you kind of end up back where you started.

So I I don't know if necessarily for some people Pure happiness is the ultimate goal. They want to, you know,

just be blissfully happy wherever they are, whenever they are. But I think other people, most people would say,

well, I'm here in this world. I'm here in this life. I don't understand it or why, but I want to be I want to be

engaged. I want to be surprised. I want to do things. I want to accomplish things. I want to want things and then

get them. Right? That's kind of the whole game that we're all playing here. Surprises are really interesting. the

sort of unpredictability. I think total bro science here, but I'm pretty sure that that's kind of how dopamine works.

That things are a bit better than you expected. That within that it means that if you for the perennial insecure

overachievers that uh cloy for control that really want to be able to the schedule is perfectly done and we know

the itinerary, we know where we're going to be at this time. you're in some ways I guess reducing down the capacity for

surprise because everything has become uh very contrived prescribed done in advance laid out your ability to be

surprised actually diminishes. Yeah. If if nothing worked out the way you expected, if it was all serendipity and

you didn't want that, you would just be a ball of anxiety. On the other hand, if everything worked out as you expected

and wanted, you'd be so bored you might as well be dead. So there's some, you know, the the river of life kind of

flows between these two banks and enjoy it. You say thinking about yourself is the

source of all unhappiness, but presumably you need to work on yourself and your weaknesses as well. So some

degree of reflection is important. And if thinking about yourself is a source of unhappiness, is this a price that you

need to pay? I need to sort of reflect inward. I'm going to have to diminish this level of happiness for a little

while and then I can use this new level. I've got my brown belt on and I can go out into the world as a brown belt.

What I'm specifically referring to that is if if you're thinking about your personality and your ego and the

character of you and uh you're obsessing over that. That's where a lot of depression and unhappiness sort of

lingers and and gets cultivated. Uh so uh thinking about woe is me, this happened to me. that happened to me. I

have this personality. I have this issue. I deserve this. I didn't get that. That's you're just strengthening a

little beast in there that is insatiable. And that's where I think a lot of unhappiness comes from.

What's the beast? It's the ego. But that word is so overused that I kind of hate to use the

word. Um, but it's like a it's a recurrent collection of thoughts that are very self-obsessed and will never be

satisfied. Very concretized as well. So, they're not malleable, not particularly

flexible. So you're just adding to them by thinking about them all the time. You're creating narratives and stories

and identities. Um but that's different from solving personal problems. So if you encounter something, you learn from

something, you're reflecting upon the learning, then you can reflect upon it, absorb it, and then just move on. But

sitting there saying, "I'm Chris. I'm Nal. I deserve this. This happened to me. That person wronged me. This is who

I am. This shouldn't have happened. I need to go get revenge on this or I need to fix that or change this." I mean that

I think is where a lot of mental illness is, you know, comes from. So it depends if you are thinking about

something to solve a problem and get it off your chest and get it off your mind. If it leaves your mind clearer at the

end of it, then I think it was worthwhile. If it leaves your mind busier at the end of it, then you're

probably going the wrong direction. Is this a a justification for detachment? uh cultivated ignorance uh

distraction. Detachment is not a goal. Detachment is a byproduct. It's it's just a byproduct

of just realizing you know what matters and what doesn't. Uh and and just for one moment on the self thing, I think

everybody craves thinking about something more than themselves. If you want to be, you know, happy to some

extent, you have to forget about your personal problems. And one way to do that is take on other problems, bigger

problems. Uh and that could be a mission, that could be s that could be spirituality, that could be kids, um it

could be caring about the planet, although I think people take that a little far, you know, and then they get

kind of oppressive and and tyrannical in support of abstract concepts. But so these can be taken too far. Just like

religion for example, just like anything in excess, anything in excess, right? Um but

generally the less you think about yourself, the more you can think about a mission or about God or about a child or

something like that. I remember Vinnie Himmath uh the founder of Loom said uh I am rich and I have no idea to do what to

do with my life and you replied God kids on mission pick at least one that's right preferably all three.

It's very liberating. Um yeah thinking I think overthinking about yourself is probably the it's it

may not be the cause of depression but it certainly doesn't help rumination. Yeah. I

I kind of had a self-induced Stockholm syndrome from this sort of a thing because I like to think about stuff and

you provide you with an endless number of things to think about. So, you're kind of Yeah, you have this um you're

the prisoner and the prison guard at the same time. And I had Abigail Shrier on the show. She was wrote this book called

Bad Therapy, sort of pushing back against therapy culture for kids, specifically for kids. there was a blast

radius that covered pretty much everything, including kind of CBT, I'm like, f like we're getting perilously