The Six Pillars of Agency: Insights from Poker Pro and Entrepreneur Cate Hall

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today, I am really excited to be talking with Cate Hall. I ran across her story in an article she wrote about how to become more Agentic: Embrace Your Agency in Life. She's a former lawyer, but has now gone on to do a number of things. And she actually introduced herself in this article.

I thought it was a really perfect way to really just capture what I want to explore in this conversation. She said, I was a Supreme Court advocate and the number one female poker player in the world, started art and perfume companies, and led operations at Alvea, a pandemic medicine company I co-founded when it set the record for fastest startup to take a drug to clinical trials. Really excited to explore these things. She outlines in this article 5 factors of agency, which we're going to dive into and resonates so deeply with my journey in the past 7 years, sort of leaving the default path too. Excited to explore these things with you, Kate. Welcome to the podcast.

[02:22] Cate Hall: Thank you. Thank you for having me on. I've been looking forward to this.

[02:26] Paul: Fantastic. So first question we always start with is around growing up. So what are some of the stories and scripts that shaped kind of how you saw the world around work, life, success, growing up, all those things?

[02:43] Cate Hall: Yeah, so I think it's funny that a large part of my life feels like it has been spent unlearning things that I learned when I was young. I think that when I was young, I got a lot of messages of, here are some narrow ways to be successful and to make sure that you're successful. And this is important because you don't want to end up stuck here in Tucson, Arizona. You had better do X and Y. Um, and I think that put me on a track in life where I was continuously seeking success for its own sake until I got to my late 20s, early 30s, and took a step back and thought, whoa, what am I doing here? I don't want the lives of anybody that's around me.

I should try to do something else.

[03:34] Paul: Yeah. So I'm guessing you were pretty good at school.

[03:38] Cate Hall: I was very good at school. Yeah.

[03:41] Paul: Growing up, like, I was always so good at at school that it was sort of like boring and easy for me.

[03:47] Cate Hall: Mm-hmm.

[03:48] Paul: Uh, but because of that, I think everyone, like, there was never anyone challenging me, like, oh, you need to figure your life out or do these things. It's just like, yeah, keep doing that. Was that sort of similar for you growing up?

[04:03] Cate Hall: Yeah, totally. Um, I think there was just always an obvious next step for me, and I didn't really sort of follow my curiosity as a general matter. I just sort of followed the path that was put down before me. I think that's probably like an oversimplification. Like nobody was telling me specifically you should do this kind of degree and then go to law school, but it was a very obvious, easy path to success, and it's kind of like nobody gets fired for hiring IBM. Nobody like gets in trouble for going to law school, I think.

[04:41] Paul: Yeah, law school's a fascinating thing. I, I saw so many peers get interested in law school because they didn't know what else they wanted to do, which seems sort of crazy looking back. And it's also one of the most gamified things. It's basically these two factors, like, I don't know if people know, but law school admissions is basically what's your GMAT or what's your GPA and what's your LSAT? And then it's basically just a ranking of schools based on those two factors. Was that sort of gamification, um, make it more appealing for you?

[05:22] Cate Hall: Um, I think it made it more legible for me.

[05:26] Paul: Yeah.

[05:27] Cate Hall: So it was just clear that there was a specific game being played and then it was a game that I knew how to win and I think that attracted me. I liked, I like winning, I like success, and where paths were a little bit more amorphous and less clear-cut, I was, I tended to be less interested in them.

[05:53] Paul: When I was in undergrad, I pulled up the rankings of consulting firms and they literally had prestige rankings. Right. And they had like these very detailed rankings, the Vault rankings. I think for law school it's, it's a different company that runs these, but you can basically just look at the list. Did you do a similar thing, sort of looking at the list of, uh, schools to get into and then after that, like the law firms and like basically pick the best offer you got?

[06:22] Cate Hall: Basically exactly that. Um, and it's funny, I can remember. Getting into Yale Law and like crying with happiness. And I look back on that, I'm like, what were you doing? Like, why were you crying? You didn't even know what law school was going to be.

You didn't know what Yale was going to be like. None of this actually mattered to you. Why were you so emotionally engaged about it? But yeah, it was just, it was just that, it was just winning. It was the most prestigious thing. It feels so silly in retrospect.

[06:53] Paul: Yeah, I— it's an interesting thing. I'm actually exploring this in my second book now, writing about how I sort of switch from one source of motivation to another. And I think for me, I got into MIT for grad school and it was sort of a similar thing that like finally the world knows I'm special. And I think for me it did come from a real sense of lack, like not feeling good enough, not feeling special enough, like wanting to be admired, especially like by the opposite sex. And I think it's tricky for me to sort of figure out what was going on because I think actually some of these things do actually improve your confidence. So how do you think about the other side of that looking back?

Right? Because there is, I'm sure you have some very useful skills from law school and working at law firms.

[07:49] Cate Hall: Yeah. So there are some useful skills left over from being a lawyer. I can review contracts quickly when I'm an executive at an organization and just like move things along faster. I can understand types of legal risk that the company might be facing and figure out whether that trade-off is worth it. I think that by far the biggest thing that I got out of law school was just the degree and the sort of stamp of success. And that has actually opened a lot of doors for me.

So it's not as though it wasn't worth anything. I think that that has given me instant credibility with a bunch of different crowds of people over the course of the last 10 years. And, you know, it's honestly put me in a position where I've been able to like co-found companies or take senior roles at companies that I didn't necessarily have a resume for just because I had that legible external signal. So I'm not complaining.

[08:51] Paul: Yeah, so how do you make sense of that when I'm sure people say, oh, you can do what you did because you went to Yale Law School, right? And I think it's sort of a yes and situation where they're missing the feeling and the challenges you actually face when you enter new domains or start something new.

[09:12] Cate Hall: So is the idea that people think that it is too easy because this credential opens doors?

[09:22] Paul: Well, I don't even know if it's that. I think it's, It's basically a worldview I had earlier in my career, which is that, okay, you do these certain like tracks to get access to things. But actually, once I stepped off that path, the things that enabled me to like go freelance, go start my own thing, go write another book, seemed to me to have much more to do with like emotional, emotional sophistication. Ability of stepping into new domains and learning things rather than anything that has to do with any sort of like credentials giving me that.

[10:04] Cate Hall: Yeah, absolutely. I think what I have done at each stage of my life professionally has had very little to do with what I've done at any other stage professionally. And so there's rarely skills that are transporting over. Things do come back around and end up being useful later. But a lot of times I'm stepping into a new domain and don't know very much at all. And I think that the willingness to do that and the willingness to kind of look dumb moving into something new is something that is not just not taught at law school, but is like aggressively selected against at law school in particular.

[10:44] Paul: Yeah. What, what did some of the people at your law firm say to you when you were thinking about leaving?

[10:54] Cate Hall: I think the honest answer is that they thought that I was having some sort of crisis, in part because I was getting divorced at the same time. So the idea to leave the law firm predated the divorce, but I decided to go ahead with it anyway. And I think that those were sort of indistinguishably linked in people's minds. So they were fine just chalking it up to Kate's having a troubled time right now. We should give her some time off. And I remember my law firm was like, you will regret this.

Why don't we give you a year-long sabbatical instead, and then you can come back? And so I took the sabbatical, and I decided not to come back. And I don't know, I, I got a fair amount of surprise from people, especially because I think where I was in the law firm, it felt clear to me that I was going to make partner in a year or so. Um, but that was also kind of part of the reason why I was leaving. Um, I felt very much that I would become entrapped if I stayed at the firm to that point because the rewards just get kind of ridiculous after a certain point and people end up getting stuck there just always saying one more year, one more year. And I watched a couple of people who are older than me do that and really didn't want to fall into that trap myself.

So I decided to just cut the cord, walk away. And yeah, I'm very glad that I did.

[12:35] Paul: Yeah. And I know you had sort of been experimenting with, uh, poker on the side. Was there some sort of energy or feeling you were getting from that that contributed to you sort of embracing the unknown and uncertainty?

[12:50] Cate Hall: Yeah, I think I just loved poker and felt fully engaged when I was playing, had it sort of consume my mental energy, and I just thought it's kind of silly to get this from a hobby. At which I could make money, like that is very easy to monetize while doing a job that I hate. So I think that the, the goal was never to play poker for a really long time professionally. The goal was to do something that I enjoyed for the first time, really, I think in my life while I was sorting out what I was going to do long term.

[13:34] Paul: Yeah. And well, the thing I find with people is there's often an activity like that that, I mean, for me it was writing on the side. I didn't even realize I should commit to writing until a year and a half after quitting. But I think something in that energy gave me enough confidence to say like, okay, I'm gonna blow up this path and give up some of the rewards without knowing what comes next. Tell me a bit more about that transition. I know there was some other stuff going on at the time, but what was the balance between like, uncertainty, not knowing what was coming, and sort of leaning into possibility and things that might emerge?

[14:16] Cate Hall: Yeah, I think it was just thrilling to me. I don't recall after making the decision to leave ever seriously questioning it again. It took me probably 6 months to a year to get to that point. Where I felt like my feelings about it were stable enough that I could trust that they would be the same a year out. But yeah, I remember when I finally finished my last court case, I immediately flew out to the World Series of Poker and just had this feeling of absolute freedom for the first time in my life. Where I knew I didn't have to do anything that I didn't want to do for some significant period of time.

And yeah, it was just, it was really incredible. And the uncertainty, the uncertainty didn't really bother me in part because I'd saved money from being a lawyer, to be honest. So I knew that I could handle some uncertainty for some period of time. Um, but I found it really exciting to not have any idea where my life was gonna head from that point.

[15:34] Paul: Yeah, this is so common in people that take uncertain paths. You, you sort of need that positive feeling.

[15:40] Cate Hall: Mm-hmm.

[15:41] Paul: Uh, I think when people only price the uncertainty as a, as like a bad thing, they have a hard time understanding why people take these leaps. Uh, but. I similarly had this like intoxicating feeling of like, oh my gosh, what have I been doing? Um, but at the same time, like I faced a lot of criticism and doubt from the people around me and I sort of struggled to come up with a story to tell people. Uh, I guess in yours you had poker, but I imagine it was still somewhat difficult to like tell your parents or explain to people close in your life, like, why or what was going on. Do you remember the stories you were using to describe it?

[16:27] Cate Hall: Yeah, I remember being really anxious about what I would tell my parents, because my parents had always sort of, my mom in particular had always sort of pushed me down the path of success. And I felt like, my achieving stuff and my going to the right law school and my getting the right job had been like a source of parental pride for her. And that quitting that to gamble professionally was going to be a blow. So I remember I wrote up a long email. I should go back and read it sometime. I wrote up a long email to them about the reasons why I didn't want to be a lawyer anymore.

And the reasons why I wanted to play poker professionally. And my parents just said, it seems like you've thought through it very thoroughly. You know your life best. You have our blessing. Which I was just shocked by, because it meant that my model of my parents had been somewhat wrong and that I had been making choices probably that were informed by that bad model of them.

[17:42] Paul: Yeah, it, this is like the number one thing I hear from people is like the approval of their parents. And often they've actually internalized their parents as like their own compass steering how they think about things. And it can keep people in these worlds for a long time. And the parents may not even know how much suffering they're going through. Uh, did your parents' support turn into active support or was it just like a neutral, like, okay, keep going, you do have our support if you need the backup?

[18:19] Cate Hall: I mean, I think it was really easy because I happened to be successful right out of the gate at poker. I had a really excellent first season. Um, and so I was getting a lot of attention and a lot of press for how well things were going. And I remember my mom just being like, well, if I had any doubts, they've been resolved. Good choice to play poker. And I kind of wanted to be like, yeah, but this is all luck.

Um, because that's really what short-term results in poker are. But I didn't say that. I was just like, yes, it was very wise.

[18:58] Paul: Yeah. And did you have a mental model at this point around like your own agency and acting into that? Or was this something you were sort of thinking about as you were entering this new domain?

[19:10] Cate Hall: I think that I had done particular things in my life that displayed like narrow types of agency. So yeah, meeting and running away with and eloping with. My husband had been an example of that where I just sort of went for it. I hadn't done that professionally though. I'd done that personally in a few different domains. And it's funny, I don't know if this was a story at the time, but looking back at it, I actually remember a particular lyric from a particular Avett Brothers song that was like, "Decide what to be and go be it." And just that lyric really hitting me hard and being a part of my like day-to-day motivation to go do something that was scary.

And I think that was like, I didn't have the word agency for that at the time, but I think that that's what that was.

[20:12] Paul: Yeah. Do you have examples, like looking back when you were younger, of like really bold moves you took? Or do you think this is something you really had to develop as you got older?

[20:26] Cate Hall: I think the examples that I have from when I was young are really pretty boring. They're like agency in particular social situations, which is really just like not acting according to the social script for how relationships should develop, or taking really intense interest in things personally, like particular topics. I think To me, it feels like I developed agency as a way of living quite late in life, which is one of the reasons why I feel like it is quite learnable for people. And something that, yeah, if people are 30 or 40 or something, it's still incredibly learnable and your life can always change significantly for the better if you focus on it, I think.

[21:25] Paul: Yeah, I think this is something I developed like in my 30s too, which is why I found your articles so interesting. Do you think there's something about being in the 30s? Like we're a bit calmer, maybe we've had some success, maybe our, our prefrontal cortex has calmed down a little.

[21:42] Cate Hall: Perhaps, um, perhaps there's something to seeing like the emptiness of success and how it is actually not very satisfying, that might be a contributor. I think a lot of it is just luck, is just like bumping into the right people who have a kind of mindset that then you can absorb. And I did that at sort of an increasingly fast rate as I got further along in my life because I was putting myself in communities that valued that more. So yeah, it was kind of like my environment was increasingly selecting people who were more agentic than me and who I could learn from.

[22:30] Paul: Yeah. What, what, how are you finding these people? And I mean, still you're, you're seeing these people and saying, I want to go further. I want to continue to align or be around these kind of people. So what was that like?

[22:46] Cate Hall: Yeah, so I think I've found a lot of these people in poker. Um, poker players have a variety of different sort of personality quirks, um, but one that is really common is a disdain for sort of set paths in life. And traditional success. And I think being around a lot of people in my early 30s for the first time who had not sort of followed the set path, who had mostly dropped out of college or never entertained it, who were really happy and successful in my life, that that was a big first step. And then I think Actually, getting involved in the rationality and effective altruism communities, which I did around the same time, was another step in that direction because I met a bunch of people through those communities who were really trying to radically rethink a bunch of different dimensions of their lives. And that, I think, opened the door further for me.

[24:02] Paul: I keep like, I keep attracting ex-poker players in my life. And I think one interesting— and I think it's spot on, like they, most of them either like dropped out of school or were playing poker online, making more than they were at their day jobs and stuff like that. But it's this probabilistic view of the world too, which I think is increasingly becoming how our economy is shifting. And it's opposed to this more deterministic world, like poker, if it's probabilistic, right? And luck is definitely involved. Law, the law path is like this most deterministic, like analytical thing you can map out.

Like you can really map out a path to partner when you're a senior in high school if you want, and you can pretty easily execute on that if you're willing to go all in.

[25:03] Cate Hall: Yep, absolutely. Um, I'm curious actually what makes you say that things in general are shifting more in this direction? Because I've observed the same thing, but I always wonder, is this an effect of the community that I'm putting myself in? Is it all VCs and poker players or something? Or is this a wider trend?

[25:25] Paul: I think the interesting tension I'm seeing is that even while people are experiencing probabilistic results, like they might end up at a company where they have a small amount of equity and they then become millionaires, right? By being a normal employee. But there's still this lag of people believe, like put your head down, hard work and you become rich. And then, but in like a friend circle, you have like this one random person that ended up at the right company. And like, to me, that's like, okay, that's just clear luck. And you're, you're seeing more evidence of this.

I mean, you're seeing examples in gambling, in poker, the attention economy, right? Like my book was shared by a YouTuber, Ali Abdaal. And it led to 10,000 to 15,000 sales of my book.

[26:22] Cate Hall: Mm-hmm.

[26:24] Paul: Right. And so I don't actually know, like, basically put your head down, focus on like doing good work in your book. It seems like the right advice, right? If you had to give somebody advice on writing a book, but I think it's based on this more like traditional hierarchical world. Industrial world, whereas probably the best thing I could do with my time if I was trying to make as much money as possible is hang out with YouTubers who have more than 5 million followers and try to convince them to make a video about my book, right? Yeah.

And so that can make people cynical too, right? Because it does disconnect the actions from the results.

[27:10] Cate Hall: Yeah, that's That's interesting. I think so. I do see this general shift in terms of, well, I wasn't alive 40 years ago, or at least sentient, so I don't really know what the world was like 40 to 80 years ago. But I feel like traditional paths to success that are more reliable, like being a doctor, being a lawyer, maybe being a consultant, were more respected and looked at as signs of the kind of success that mattered to a greater extent in prior times. And now there is a lot of emphasis on people getting ludicrously rich from ideas that they're able to contribute, or I guess ways that they're able to benefit from those ideas. So we've just shifted toward a model where like software companies that have, are able to have 1,000x returns are driving a lot of the economy, or other industries that are VC investible are driving a lot of the economy.

So the most sort of prestigious thing that you can do in many circles is go be a part of that economy, uh, take on a lot of risk relative to being a lawyer, being a doctor, but have the potential upside of being really successful and respected.

[28:47] Paul: Yeah, it's, it's an interesting trend. Like, I think even I, I have a bunch of friends now who basically like made it in the, the ZIRP economy of low interest rates and got bought out and put it like join these startups early and made out really well. But their goal from the beginning also was like, okay, I'm going in, I want to find lottery tickets that have high odds of success. And like, this was the whole goal. Whereas like you can get slowly rich in a job, but you can't sort of play that lottery ticket game. And it does just reshape how you're thinking about things.

So I guess it'd be interesting to see how you thought about like work when you shifted from law where like the law salaries are so predictable, right? It's like everyone pays the same. It goes up a certain amount every year. And then when one firm increases the salaries, everyone else increases them too.

[29:53] Cate Hall: Yeah, totally. I think playing poker was a kind of unusual edge case of this because playing poker is— yeah, this is actually interesting to think about. Playing poker is kind of one of the highest risk activities, I think, um, in that you can easily show up to work every day, work really hard, study really hard, actually make excellent decisions, and end up losing money for a month straight and basically having to pay in order to do your job. And that is, that is really psychologically taxing. Downswings are just awful to go through. And I think that it's possible that this gave me a lot more risk tolerance overall.

Because now when I'm like at a startup and I have a bunch of comp and equity or something, the fact that I'm earning a salary that I can live on makes it feel incredibly stable. Like if I have a permanent position somewhere, that just feels incredibly stable in relation to I might, you know, lose a significant amount of money and have nothing to show for myself and be in a worse position because I'm doing this job. I don't know if it would feel that way if I had stuck to law.

[31:31] Paul: Yeah, so this might be a good way to transition to the agency article, and I'll link to this. You basically outline 5 things. And so the 5 things are court rejection, seek real feedback, increase your surface area for luck, assume everything is learnable, learn to love the moat of low status, and don't work too hard. So 6 things. I counted incorrectly, but I think the interesting thing here is the 6th one to start with, which is don't work too hard. And I love what you said, like you don't trust anyone that hasn't burned out because you, you basically realize the game was to not burn out, right?

Survival on any path is ultimately what you're aiming to do. And so if somebody hasn't burned out, they don't really know what the edges are, the limits of any sort of activity. Um, and poker is like the ultimate manifestation of that, right? You, um, are trying to survive tournaments, but you're also trying to survive the long game. So what does that have to do with agency?

[32:40] Cate Hall: I think I might respond to the general case first, and then we can see if we can tie it back Okay. I think that people who haven't experienced burnout have a really wrong model of what it does to somebody's brain. And this is a lesson that I learned the hard way repeatedly. I burned out at the end of college. I burned out as a lawyer. I burned out a bit at a not not too distant job.

And I've sort of learned to recognize what is happening only through repetition, unfortunately. But I think people have the, the sense that burnout is just getting really tired of working. And if that happens, taking some amount of time off is going to be able to fix it, or some other intervention is going to be able to fix it. And I think it's a much, much deeper thing that can take actually years to recover from, and some people just don't recover from it. So it's actually fairly catastrophic in my experience, or it can be, to burn out of a profession. Um, and I don't think that that is taken seriously enough.

[34:03] Paul: Yeah, I totally agree with that. I basically burned out 7 years ago.

[34:07] Cate Hall: Mm-hmm.

[34:08] Paul: And I would say it took me 3 to 4 years to really recover. And I think it was just a total disconnect from what I thought I valued and what I was spending my life doing.

[34:20] Cate Hall: Mm-hmm. Yeah.

[34:22] Paul: But it became an advantage because I then had this mental model of don't ever come close to that state again. So my entire path became avoid anything that looks like my former path. And I sort of stumbled into a lot of accidental great things in how I structure my life through that. And one of them was literally don't work too hard or not don't work too hard. Like don't work too long on stuff I don't care about was basically the principle.

[34:54] Cate Hall: Mm-hmm. Yeah, I think that, that seems exactly right. In some sense, all of poker was me recovering from being burned out as a lawyer. So I had a pretty long period of it as well. Um, yeah, I think that there, there can be silver linings in what you learn about yourself and what you learn about the world, but it is a costly lesson to learn. And then you end up avoiding a bunch of stuff that, you know, might otherwise be good.

Like I avoid law as to sort of like neurotic extent, you know, if, if, if something needs to be reviewed at a company, I'll do it if there's like a really good reason to, but I'm trying to send it to outside lawyers all of the time because I have this reflexive ick reaction to anything that is law related. And I wish that I didn't have that. Like, that is useful to guide me away from stuff that is law-shaped, but it would also be cool if I could exercise some of the skills that I learned in that context without feeling emotionally wounded by it.

[36:09] Paul: Yeah, I, I resonate with that too. I'm 7 years from leaving consulting and I actually realized in the past year or two, I'm I have this fear of success, probably. I don't even know if that's the right framing, but like, I'm so scared to double down on anything that's not my writing or the thing that brings me alive because everything feels like it might turn into the old path. But in the last couple of years, I've actually pushed my limits and sort of just find myself, oh, I'm okay. I can, I can go a little further. It's going to be okay.

And man, yeah, it just takes so long.

[36:54] Cate Hall: Yeah. I have like paranoia around money, I think for the same reason. I'm very suspicious of myself when it comes to money and compensation for jobs. So if if something is high paying, I have a tendency to discount my own interest in it. And I think that's just because chasing money as a lawyer or law student led me to such a bad place that I don't want to risk it. So I kind of, I kind of like cut myself off from some paths that would earned me a bunch of money for that reason.

[37:37] Paul: Totally resonate with that. Number 2, learn to love the moat of low status. I love this phrase from Sasha. I've also called it the status tax myself, which is that I think there's an arbitrage opportunity if you're actually willing to pay the status tax because it's not that bad.

[37:59] Cate Hall: Yeah, that, that's the secret. It's actually not that bad. Yeah. I think this is a really, really big one. Like, it holds people up a lot because people are extremely afraid of looking dumb. And I think it causes them to overestimate the number of situations in which they will actually look dumb.

Like, it engenders a kind of paranoia about it. But it's also just fine to look dumb some of the time.

[38:33] Paul: Exactly.

[38:35] Cate Hall: Or at least that's my experience. Now, I can't discount the idea that it's easy for me to get into the mode of low status because I've been successful at a bunch of other things, and people see that and know that I'm not like an idiot. But I think that people in general are too paranoid about it. I have certainly been too paranoid about it. At other points in my life, where I just didn't want to ask a question. Like, it felt physically painful to me to ask a question that I thought that the other person thought was dumb.

Because, yeah, it— I just should know for some sort of cosmological reason what the answer to all of these questions were. And that kept me from asking so many questions.

[39:25] Paul: So this is number 3, court rejection. And this is such a perfect example of asking a silly question, which sort of shocked me when I read it. I'm planning to start an organization similar to yours. Would you consider letting me run yours instead? You asked this to somebody, which is like, man, that's actually like a really convenient way to start a company.

[39:51] Cate Hall: Right? It's a good shortcut.

[39:56] Paul: Yeah, it'd be like if you were like, hey Paul, can I just have your podcast here and you stop running it?

[40:03] Cate Hall: Yeah, I think, I think those were— so I did that with two people, and I think that there were both situations in which it made a certain amount of sense because, uh, they were kind of casually considering people for an executive role or something like that. But I have pulled this kind of move on a few occasions. And I think most of the time people just think it's ridiculous. But You really only need like one maybe for it to pay off as a strategy. Yeah, so I don't know if I recommend that particular one, but it's a good example of how aggressive you can get with like asking for ridiculous things.

[41:01] Paul: Yeah, I actually went through this exercise and realized I had only asked to go on podcasts and that I knew I would get Um, yeah, a lowdown. And I actually put out a bunch of asks for podcasts. I basically got ignored by all of 'em. I was trying to go on like a big podcast, talk about my book. It was fine. It was totally fine.

Yeah. They just ignored me and I got some nos, but I don't know, maybe it'll turn out into a yes in a year or two.

[41:33] Cate Hall: Yeah. And this is a good example of something where it feels like This is a form of delusion that I was clearly living under for a large part of my life. I was terrified of rejection for the first 30 years of my life and really did kind of the same strategy, like tended to only apply for things that I knew that I would get. And getting some experience with getting rejected for stuff was so freeing for me because it opened up a bunch of possibilities for more ambitious goals that aren't there if you need to have success as like the default condition.

[42:19] Paul: How do you define ambition now?

[42:22] Cate Hall: Oh, interesting. So I was asked a related question recently, which is— was in the context of a job discussion, um, and The question was like, how do you decide what things are ambitious enough for you to do? And my answer was, it's something like, there's a greater than 1% chance that when I look back on this in 10 years, I decide it's like the very best thing that I could be doing, um, based on the information that I have now. And I think that 1% could sound low, but it's actually a really high standard to meet. And almost no jobs in a decent period of time that I was looking met that criterion. Because yeah, there's always more research that you can do.

There's always, you know, there's always other things that might come up. But I think if it can meet that criterion, I know that it's something that really matters. Um, and that's good enough.

[43:37] Paul: I love that. This is basically a similar thing that caused me to double down on writing my second book recently. Because I was just spending all my time doing all these marginal activities, but then I said, okay, at the end of my life, what am I going to be happiest about? And basically it was like, write the book. Um, what do you do to seek real feedback? So this is your fourth point, um, seek actual real feedback.

[44:09] Cate Hall: Yeah, so one thing that I mentioned in the piece, which I highly, highly recommend, is having an anonymous feedback forum that is just like publicly accessible, that you sort of advertise People, no matter how much you signal openness to feedback, people don't like to give it if it's negative. It's just too painful and it's sort of a tendency that is bred out of people. So having that outlet, I think, is really good. The other thing is, I mean, in professional environments, it's somewhat easier because you can take steps to sort of set up a healthy feedback culture and both give people feedback and solicit feedback enough that it becomes commonplace. But I like giving people opportunities to do it, not just in professional contexts, but in personal ones too.

[45:08] Paul: What's some of the most valuable feedback you've gotten?

[45:12] Cate Hall: The piece of feedback that I got I mean, I can't, I'm sure there's a ton of feedback that I've gotten in person that has been really, really valuable. And it's harder to bring to mind than like what was the most valuable thing that ended up in my inbox. And the most valuable thing that ended up in my inbox was a comment from somebody that I clearly worked with who was almost certainly a subordinate who said, that they found it really difficult to tell if I liked them, that I was really harsh and cold, and that they found me intimidating. And that sort of, that sort of confirmed something that I had been trying not to see about myself because it would be inconvenient to have to fix it. But That made it hard to avoid.

And so after that, I spent quite a bit of effort trying to become better about that and have like warmer, more authentically engaged relationships with the people that I work with.

[46:24] Paul: I love that. The next one was, uh, assume everything is learnable.

[46:30] Cate Hall: Mm-hmm.

[46:31] Paul: It sounds, sounds obvious and simple, but I think it's actually hard. It's actually surprising to me how little learning people seem to actively throw themselves into after they're like 5 years into a career.

[46:46] Cate Hall: Mm-hmm. Yeah, and I think that the really big thing for me is that personality traits can be learned. I think that there is a ton of pop psychology that says that isn't the case. But it's based on sort of the observation that people rarely do change. And that's not surprising because, I don't know, all of modern discourse, I think, operates under the assumption that you're just like a particular kind of person. And that is really, that's basically impossible to change.

And I think that there are way, way more degrees of mental freedom than people realize. Some people discover this through like the contemplative path and meditation, and some people discover it through emotional work. But I think a lot of people go their whole lives feeling like they're, you know, there may be things that they don't like about their personality that they just feel sort of powerless to change because they are just a certain type of person. And I think that this is true of almost nothing. I think general intelligence is difficult to change. That's, that seems like pretty close to fixed, though you can do some stuff, arguably.

But most other big determinants of success seem to be pretty malleable.

[48:23] Paul: Yeah, it's, it's been interesting to observe myself change in my 30s, and it really undermined a lot of my own beliefs in that, oh, you are this person. And it's funny how much of that was driven by, I think, like a career-first view of the world, which is like, I almost think like, I don't know if this happened to you, but I had partners in consulting and the people around them be like, that's just the way they are. Like, you have to learn to, to deal with that. And like so many people embrace that belief that it sort of becomes the reality and you can't see that there is another way to be. And I actually wrote an article one time around this guy Donald Super's model of career and life. And it was basically ages 15 to 24, you're exploring.

Then you establish yourself until the age of 44, then it's maintenance, and then decline. And this is like the most depressing view of life, but I think was very prevalent in the industrial world where like there were limited options and there was a set life path and things like this.

[49:37] Cate Hall: Yeah, that's fairly horrifying. Um, Yeah, I think, I think probably not to that extent, but a pretty defeatist attitude is common. And I think people just vastly, vastly underestimate the extent to which they have the ability to shape their lives, even after they've gone down a particular path for a while. And there's this general, like, generally agreed-on delusion that that's the case and that people are just sort of stuck in their careers and it's too late to switch to a new thing, um, that pervades huge swaths of society.

[50:31] Paul: So number 6 is imagine your surface area of luck. I'd love to hear first, how do you— what do you mean by surface area of luck? And then how do you imagine that?

[50:45] Cate Hall: Yeah, it's funny. So I totally thought that I invented this concept, but then after I wrote this, I read it in a Paul Graham essay from, I think, like 10 years ago. So I clearly absorbed this at some point and just ripped it off unintentionally. But I think it's a really, it's a really useful concept. So the idea is just basically, you know, say you have projectiles that are trying to hit a target. If you have a very big target, it's more likely to hit than if you have a small one.

And increasing the surface area of something just gives a bigger target. So increasing your surface area for luck, it assumes that a lot of the determinants of success are luck-based. It's like what, what opportunities you stumble over, what collaborators you happen to bump into. And I think that is really true. And most successful people will say that that's true as well, that a lot of their success in life was based on luck. And so the idea is just like go out in the world and make a lot of contacts, try a lot of stuff, sort of flail around and give— create a lot of opportunities for luck to find you.

[52:15] Paul: This is my book marketing strategy. I gift books and I leave them around the world. I basically everywhere I am, I leave them on park benches or I drop them in cafes and I leave little notes in them. So I've done over 1,000 at this point. And yeah, I don't know what's going to emerge from that, but it's the same, like optimistic sort of like, who knows? Would you give me other advice on expanding my surface area even further?

[52:49] Cate Hall: You know, the piece of advice that I would give to somebody, which might be you or might not be you depending on your disposition, I think networking has negative connotations and for good reason. And I avoided it, like anything that might be described that way for most of my life. And felt on some level, though it wasn't really examined, that I was willing to accept the trade-offs for that. I think I really failed to appreciate how big the trade-offs are and how valuable it is just to meet a lot of people who are interested in the same thing that you are and who are doing projects in the same area. And since I started making an effort to be a social person in the context of my profession, which didn't happen very long ago, um, I've seen it have like a multiplying effect on my effort and everything becomes a lot easier.

And so for introverts out there, I would say it is a really valuable thing if you can learn to force yourself to do it and It is learnable, like many things are.

[54:12] Paul: Yeah, I actually had 400 curiosity conversations with people before writing my book, and I'm much more extroverted. So this is like fun for me. But I really think that people get the tradeoffs wrong, that there is so much upside to just these random encounters. But they can feel costly, especially if you have some sort of like, oh, this work will get me X or make me feel better about finishing stuff. And for some reason, I've just always been good at dropping the ball on sensible work to do the more fun stuff of just hanging out with people.

[54:53] Cate Hall: That, I mean, that's a huge value add, I think. My husband has a piece I like on the value of extroversion and It's unfortunate, but it's just real. Extroverts have a huge advantage in life.

[55:08] Paul: Um, especially in the US, I think probably anywhere though.

[55:14] Cate Hall: Yeah, that might be right.

[55:16] Paul: It could be more valuable in other places. Like I think in Taiwan where my wife's from and where I lived for a while, extroversion's probably higher return because it's, um, less of a social ideal. Hmm.

[55:29] Cate Hall: Okay. I think, yeah, it probably is valuable just about anywhere for reasons related to increasing your surface area for luck. And just because people like being around extroverts, which I had to come to terms with as a big, big introvert.

[55:50] Paul: Did you have a script like, okay, I am the kind of person I just need to work hard. I'm not going to rely on social connections. Or anything like that that you had to unlearn?

[56:03] Cate Hall: Yeah, absolutely. I, I think my approach would all— was always, I'm gonna be so excellent that it doesn't matter that I don't wanna do various things that other people say are important. And I, I think that I was able to achieve a level of success doing that that was like adequate. To me, but that kept me from being able to perceive how much I was being handicapped by that nonetheless. It's like, like adequate performance is the enemy of great performance, and it can be really difficult to see opportunities, like massive opportunities for improvement if you're doing like fine by your own standards.

[56:51] Paul: So I have a decent amount of listeners here. How can people listening help you now, now that you're expanding your own surface area of luck?

[57:00] Cate Hall: Oh my gosh. There is literally nothing I want or need in life. So I don't, I don't know how to answer that.

[57:11] Paul: That's a very—

[57:11] Cate Hall: that's my answer. Yeah.

[57:16] Paul: This is always my response to I have to sit down sometimes and like come up with ways I might want help in the world.

[57:26] Cate Hall: Yeah, I mean, there's like domain-specific things. Like if you know a synthetic bio researcher who is trying to scale up fermentation practices, talk to me. But it's all that kind of thing. There you go.

[57:40] Paul: You never know. They could literally be listening right now and we could solve that problem. I'm glad we're expanding the surface area of luck. Um, anything else since writing that article? I know it got a pretty big reception, um, that you'd add to your model of agency.

[58:02] Cate Hall: I think there's just a lot more to talk about. Um, that article, you know, I started with a list of 10 things that probably could have been 20 things, and I just picked the few that were easiest to write about. Yeah, I think once you start viewing your life through this lens of like, how can I create more opportunities and more, more like questions for myself? Like, how can I learn to see more things as optional or based in choice than I currently do? I think it is a like, it was for me a revolutionary way to see the world. And I find that I'm consistently able to like find deeper levels of that.

[58:51] Paul: I love that. Is there a place you want to send people to follow along? Do you plan on writing more on the blog? Other places you want people to connect with you?

[59:02] Cate Hall: I'm in this really kind of predictable and pathetic place with the blog, which maybe naming it will be helpful. The first piece that I wrote performed so well that I'm like, oh, nothing, nothing will live up to it, you know? And I, I could predict this failure mode ahead of when it happened, and I'm watching myself do it and be like, that's really dumb, but it's happening nonetheless. So hopefully there will be more on the blog soon. I just need to get over this mental barrier for myself.

[59:36] Paul: I have a great exercise for you from a writing coach I love. his exercises to just write about pizza. Cause this is from Sasha. Oh, write about pizza because everyone has a story about pizza. So maybe that can be your next post.

[59:56] Cate Hall: Yeah. It's funny cuz yeah, Sasha, my husband is a writing coach and I'm like, man, I would be falling into this trap.

[01:00:08] Paul: Awesome. Anywhere else you want, uh, people to find you or connect with you? I'll link up to, uh, Twitter and your blog.

[01:00:16] Cate Hall: Yeah, that, that's the like platform that I tend to check if I check anything.

[01:00:22] Paul: Fantastic. Anything else you wanna leave us with today, Kate?

[01:00:26] Cate Hall: I think that does it. Thank you so much for having me on. It was really a pleasure.

[01:00:30] Paul: Awesome. Love diving into this and, uh, excited to see what sort of, uh, where your agency takes you next.

[01:00:39] Cate Hall: Thank you. You do.