Cate Hall on Taking More Chances And Other Ways to Increase Your Luck

Summary

Forever35 Podcast Summary

Episode: Cate Hall on Taking More Chances And Other Ways to Increase Your Luck
Hosts: Doree Shafrir & Elise Hu
Guest: Cate Hall
Date: August 10, 2026

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Episode Overview

This episode features Cate Hall, author of You Can Just Do Things, former Supreme Court clerk, top-ranked female professional poker player, and tech entrepreneur. Cate shares her multifaceted life journey—from high-powered law, to poker stardom, through addiction and recovery—and discusses her actionable insights on regaining personal agency, overcoming the fear of embarrassment and rejection, and increasing serendipity ("surface area for luck") in one's life. The conversation is honest, rich with personal anecdote, and full of tangible advice for those feeling stuck.

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Key Discussion Points & Insights

Cate Hall’s Wild Life Journey

• Cate walked listeners through her non-linear career: from Yale Law and top law firms (including clerking for the Supreme Court), to the upper echelons of professional poker, into years of drug addiction, and finally into sobriety, tech, and writing.
• Her new book, You Can Just Do Things, is described as a manual for reclaiming agency, particularly for those feeling paralyzed or stuck.
  • “It’s very actionable … a good manual if you feel kind of stuck.” —Doree [01:31]
• Cate emphasizes that her practical tools for agency were born from clawing her way back up after addiction.

Addiction, Recovery, and Agency

• Cate credits her sobriety to "grace" rather than any single method, highlighting how addiction recovery can be mysterious and highly individual ([18:48]).
  • “There are so many rock bottoms on the way down … you hit a lot of things and you’re like, maybe this is the rock bottom.” —Cate [19:30]
• The process of rebuilding life started slowly after inpatient rehab, with modest aspirations and incremental steps ([20:44]).

The “Crisis Manager” Mindset for Getting Unstuck

• Cate recommends adopting a “crisis manager” mindset: imagine an emotionally detached expert parachuting into your life to solve your problems—focusing only on the present and next step, not past failures ([21:00]).
• This mindset helps separate one’s sense of self from prior shame or stuckness.

Overcoming Fear of Failure, Embarrassment, and Rejection

• Cate discusses the “moat of embarrassment” and “path of least embarrassment”: the fear of being seen as a beginner at something is a major impediment to personal growth ([25:14]).
  • “In order to really get better at something, you have to allow people to see you being bad at it.” —Cate [26:41]
• She advocates direct exposure: embarrassment and rejection don’t magically disappear with enough positive thinking—they get easier through practice and habituation ([28:10]).
  • “You just do the thing anyway, you experience the embarrassment, and … it is actually not nearly as bad as it is in your imagination.” —Cate [29:19]
• Rejection and failure are positioned as vital learning tools—like how babies repeatedly fail on the way to walking ([30:54]).
  • “The further you can get away from thinking that way, the more you can be back in this baby mindset where you're actually learning so quickly because you're constantly getting feedback from the world.” —Cate [31:50]

Rejection Sensitivity, ADHD, and Habituation

• Doree asks Cate specifically about ADHD and its link to heightened rejection sensitivity ([34:08]).
  • Cate reflects she herself has ADHD and relates deeply to the avoidant behaviors described—like dreading calling room service ([35:23]).
  • Cate advocates for exposure and habitual practice for building tolerance, whether or not one has ADHD.
  • “I think ... the techniques will work too, for people who have these things.” —Cate [36:26]

Increasing Your “Surface Area for Luck”

• Cate discusses “giving yourself more chances to get lucky” as a key principle for agency ([38:26]).
  • Citing Steve Jobs, she notes life-changing encounters are often unpredictable, so taking more “shots on goal” is vital.
  • She recommends internet writing—especially Substack—as a modern, lower-barrier way for introverts to increase exposure and chance encounters.
  • “Increasing your surface area for luck is basically just like creating opportunities to encounter a wider range of people and more of them.” —Cate [39:22]

Lessons from Poker

• Cate shares how tournament poker taught her to think in terms of “expected value”—accepting regular loss as the price of modest chance at a big win ([43:21]).
  • “Your tournament life is ... long series of losses punctuated by occasional big wins that more than make up for the losses. The question is, what kind of person wants to do this for a living?” —Cate [43:29]
• This approach applies to careers, entrepreneurship, and even dating: it’s about tolerating many failures in search of rare, pivotal successes.

Applying Agency (and Who Needs It Most)

• Cate’s mission is to extend agency not to the already brash, but to the rule-followers and the hesitant—“the best who lack conviction”—so their decency and values can have more influence in the world ([45:59]).
  • “People who are ... higher in dark triad traits tend to be more naturally agentic ... So my book ... is to ... extend the thinking behind agency to a wider group of people who are going to apply it in more pro-social ways.” —Cate [46:01]

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Memorable Quotes & Moments

On Multiple Reinventions

• “She’s lived a lot of lives.” —Elise [02:12], on Cate’s wild resume from law to poker to tech to writing.

On Recovering from Addiction

• “You cannot give somebody else the will to recover. And that is ... the irreducible requirement of getting sober.” —Cate [24:17]

On the Fear of Looking Foolish

• “It’s really hard for us to actually envision the end state of being better at something and ... really easy to imagine ... embarrassment of temporarily being bad at something in front of other people.” —Cate [27:11]

On Building Luck

• “You can't plan to meet the people who will change your life.” —Cate quoting Steve Jobs [38:34]

On Book’s Purpose

• “The goal is to ... extend the thinking behind agency to a wider group of people who are going to apply it in more pro-social ways.” —Cate [46:01]

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Timestamps for Key Segments

• Intro & Cate’s Background — [01:08–02:45]
• Cate’s Journey: Law, Poker, Addiction, Recovery — [16:42–18:39]
• Addiction Recovery, Grace, and Agency — [18:48–20:44]
• How to Get Unstuck: Crisis Manager Mindset — [21:00–22:40]
• Overcoming Embarrassment, Failure, Rejection — [25:14–31:50]
• Rejection Sensitivity and ADHD — [34:08–37:38]
• Increasing Luck & Serendipity — [38:26–41:48]
• Poker Lessons for Life — [43:17–45:48]
• Applying Agency as a Rule-Follower — [45:59–47:21]
• Where to Find Cate Hall — [47:26–47:34]

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Natural, Humorous, and Self-Aware Tone

The hosts keep the conversation grounded and relatable, returning repeatedly to their own moments of self-doubt, parental struggles, and practical attempts at making life less overwhelming. Cate’s candid reflections on failure and self-improvement are both sobering and oddly reassuring.

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Additional Resources

• Find Cate Hall: Substack at Useful Fictions [47:29]
• Book: You Can Just Do Things (Out Now)
• Forever35 Community: Questions, micro joys, and dermatologist Q&A submissions encouraged.

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For listeners seeking practical advice on reinvention, risk-taking, and overcoming psychological barriers (with a big dose of honesty and dry humor), this episode delivers both the tools and the hope to ‘just do things’—even if you feel stuck.

Transcript

[A]

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[B]

It was a mansion.

[A]

And with three times the points on dining, we ordered a wagyu steak dinner

[B]

and that pistachio gelato was too good.

[A]

So where should we go next year?

[B]

I've got ideas.

[A]

Chase Sapphire preferred the card that's preferred for a reason. Cards issued by JP Morgan, Chase bank and a member FDIC subject to credit approval terms apply.

[B]

Hello and welcome to Forever 35, a podcast about the things we do to take care of ourselves. I'm Dory Shafri, Career.

[C]

And I'm Elise Hu, and we're two friends who like to talk a lot about serums.

[B]

And today we have Kate hall, who, I mean, I think the best way to describe her is, like, fascinating person.

[C]

Yeah, she's worn a lot of hats.

[B]

She's worn a lot of. She's lived a lot of lives, honestly. She went from being a corporate lawyer, like on the partner track, Yale law

[C]

graduate, Supreme Court clerk, I think at

[B]

one point super legit, to leaving that all behind, becoming a professional poker player, which is where I first, like, learned of her because it was. It coincided with when I became very interested in poker. And so I was like, who are, like, the big female poker players? Like, there's not a ton of them. And she was also very active on Twitter at the time. And so I followed her and she was like a great Twitter follow. And then she kind of like, dropped off and like, the pandemic, like, I just kind of like, lost track of her. Turns out she was addicted to drugs for three years and she got sober and started working in tech and wrote, like, she wrote a couple books. And her new book is called you Can Just Do Things. And it's about. It's like, all about how to take agency in your own life. I found it very timely. Okay, good for me personally. Yeah. So, yeah, I thought her book was like. And it's very actionable. She's a lot of, like, exercises in the book of, like, how to do things. And yeah, it's. It's a. It's a good. It's a good, like, manual. I think if you're at a place in your life where you feel kind of stuck. And she's just, like, super smart and cool.

[C]

Yeah, she was very wise. It seemed like she was wise beyond her years. And she had some takeaways, actually, from the book. We kind of drilled into a few of the things

[D]

in.

[C]

You can just do things. So I've pulled out some of those things and put them in our newsletter, which is out now on our Patreon, but also goes into your inboxes if you already subscribe. And that Kate conversation is coming up later. But here we are. Here we are in August, and we're already winding down our summers here on the west coast because school kids are going back to school in Arizona, in California and Washington and Oregon, and it's wild. Like, it's gone by so fast, and in some ways, it's dragged on. We've talked about the elasticity of time. But what are you. What are you looking forward to in the school year? What do you. What do you have coming up?

[B]

Well, you know, Henry. Henry's starting a new school, so a lot of unknowns. I'm currently, like, trying to negotiate with the school department about his bus stop because the one that was assigned to him is, like, very far from our house and has a super early pickup. And I was like, are there any other options? So trying to figure that out. Like, there's just a lot of, like. I don't know, it feels like there's a lot of, like, bureaucracy and setup that I'm trying to accomplish and, like, navigate all of that in a new school and, you know, just, like, new. Everything is new. So, you know, trying to go into it with, like, an open mind and curiosity and also be like, nothing is permanent if this doesn't work for. For our child or our family, like, he can go to a different school.

[C]

How is he feeling? Is he excited?

[B]

He seems neutral.

[C]

Okay.

[B]

Honestly, like, he doesn't seem super anxious, but he also doesn't seem, like, excited. It's just sort, like, he's just sort. It's sort of like he's accepted it. You know what I mean?

[D]

Yeah.

[B]

So I don't know. I think he. I think he so doesn't know what to expect. That it's just like, how can he even. Right. Fathom what it's going to. You know, what it's going to be like. Right. So I don't know. We'll see.

[C]

Issa has expressed. She is like, I don't know about this transition to middle school. I'm scared to go to middle school. There's so many kids. Is Ava going to talk to me? Ava's probably not going to talk to me because she's going into sixth and Ava's going into eighth.

[B]

Yes. Ava's like, big man on campus.

[C]

Exactly.

[D]

And.

[C]

And literally, like, physically.

[A]

Right.

[B]

She's very tall,

[C]

as she says. She hype mogs me. She's like, I'm hype mogging everyone at school. I. I'm hype mogging you. So, yes, she mogs all. And of course Ava's going to talk to her sister. I know that she's going to be so excited to see her. And in fact, she's actually going to volunteer at her middle sister's sixth grade orientation.

[B]

Oh, my gosh.

[C]

Yeah, I think it's really sweet. And so I think it's gonna be chill. And. And Issa has so many friends, but Issa tends to be a little bit more anxious. And so she's just asking a lot of questions. But she, like, doesn't start expressing all of this until very late at night right before she's going to bed, which is right before I want to be in bed. And so, yes, yesterday she wanted to ask me, like, a series of questions at nearly 10 o', clock. And I was like, can we, can we schedule a zoom for this?

[B]

Right?

[D]

She's so cute, though.

[C]

So, yeah, I think she is the one who's, like, most kind of expresses the most trepidation about school.

[E]

Okay.

[C]

Ava's excited to be an eighth grader because finally, yeah, she's like. She's all about her back to school hall, which we talked about on the casual chat. And then Luna is going to be on her own in elementary for the first time without sisters, because ever since she's been in kindergarten, she's had a sister, and so now she's the only one. And I think that that's actually an opportunity for her to shine. And her personality is a little bit different, too. So I think this is great for her to exercise more of her own personal agency. Speaking of Kate Hall.

[B]

Yeah, totally.

[C]

Kate hall writes about personal agency. And so we'll just bring it. Bring it back to Kate hall and listeners. If you have micro joys, I just want to put out a call out. We have two call outs for y'. All. One is love to hear your micro joys and how you're enjoying the summer or how you're trying to kind of summer max before it all comes to an end at the unofficial end of summer Labor Day. But then also my dermatologist, Dr. Jenny Wong, who has been on the show before. We are still soliciting questions from the Forever 35 listeners. Questions for a dermatologist. Any skincare stuff or skin product stuff or skin procedure stuff that you want to ask about, please email us at

[B]

forever35podcastmail.com you can also call or text us at 781-591-0390 with your questions. Um, you can also still send us, you know, general comments, questions, feedback, concerns, thoughts, conversation starters for our you ask we answer episodes which we are doing every other week now. So again, that's 781-591-0390.

[C]

Love a phone call.

[B]

Yeah, we love a phone call. And Our email is forever35podcastmail.com My micro

[C]

joy is actually phone calls and this is what made me think to do the shout out because I had an intern when I worked at NPR who worked, I think, like maybe she was only there for a semester, it wasn't that long of a time. But she was a really impressionable intern. And I just thought, I mean, this girl was more accomplished and more interesting than me than. Which was true of pretty much all of the fellows and interns at npr. Yeah, and her name was Emily and I just loved her. And we stayed in touch like as she entered journalism and we will go kind of a long time without catching up. And I think I hadn't spoken to her in maybe a year or two, but she reached out and she was like, could we do a phone catch up?

[B]

Oh.

[C]

And there was no particular agenda, but we did this phone catch up last Friday and it like, I just found it to be so connective and like supportive and warm and we like just talked about the stuff. You know, she's going through some things with her family and some health stuff. And you know, I shared what was going on here with me and my own family and my health stuff. And it just, I don't know, I just loved being on the phone because I think that it's so easy to send each other DMs on Instagram and I do see my friends on Instagram and we connect that way. And I think it's great to be able to have these touch points, whatever, in whatever format. But there was something just really rich and a little bit deeper and got below the surface just by talking on the phone for half an hour. Just going on a little reverie in praise of the old fashioned phone call and just reaching out to a friend and saying like, hey, can we do a call? Just a catch up call.

[B]

Yeah, I think. I think that's such a good point. Well, Elise, before we get to Kate's official bio, I do just want to remind everyone that Our website is forever35podcast.com. We have links there to everything we mention on the show. Our Instagram is reverber35podcast. Our Patreon is at patreon.com forever35. I want to give a shout out to my dear old one of my oldest friends, Alison, who recently joined the Patreon. Thank you, Allison. Hope you're enjoying the casual chats and everything else. For $5 a month you get those casual chats which are now on video. You also get live casual chats every couple of months, access to our community chat on the Patreon app, and a lot more. And at $10 a month, you also get ad free episodes and a shout out on the podcast each and every month. So, Alison, listen for your shout out. The next time we do that, you can shop our favorite products at shopmy us./forever35. And now I will introduce Kate officially.

[C]

Yes.

[B]

Kate hall is the author of you Can Just Do Things which is out now. She writes about personal agency from the perspective of someone who learned it late in life to make it easier for you to learn it too. Everything she knows about agency comes from her personal experience as a former Supreme Court attorney, number one ranked female poker player in the world, drug addict, biotech founder, and the CEO of a multi billion dollar foundation, in that order.

[C]

She's lived a lot of lives.

[B]

She's lived a lot of lives. We are going to take a short break and we will be right back with Kate.

[C]

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[E]

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[B]

Kate hall, welcome to Forever 35. It's really nice to meet you.

[D]

So nice to meet you guys. Thank you so much for having me.

[B]

Yeah, of course. What is something that you do that you would consider self care?

[D]

I have a lot of really lame answers to this. I like my core self care is doing the entire New York Times game section religiously every night. I'm a big crossword puzzle person, but pips and connections have also become part of my daily routine. That's like my big unwinding thing.

[B]

I love that. Do you play Crossplay also? Do you play like their Scrabble ripoff?

[D]

I have not played it. I think I'm a little too competitive

[B]

maybe for it fair.

[D]

I've tried. I've tried like doing the crossword at the same time as my mom, who's also really into crosswords and always devolves pretty quickly.

[B]

Oh, okay. Maybe not fun.

[C]

It is a great way to stay connected to mom too. Are y' all in the same location? Are you geographically?

[D]

No, no, no. She lives in Arizona. I'm in the Bay Area.

[C]

Yeah. So it's a great way to stay in constant communication with your mom. That's awesome.

[B]

That's so fun, Kate. You know, I started following you, I think right around the time that you became a professional poker player.

[D]

Whoa.

[B]

Yeah, on social media. Because I had started playing poker and I was like intrigued by, you know, women poker players. It's like, oh, this woman seems really cool. So I started following you on Twitter. So yeah, so I've been, you know, I've been following you for a long time, but I didn't really know until I read your book about every, like all the crazy stuff that had happened in the last few years. So before we get to our book for our listeners sake, can you just kind of walk us through your pretty wild career trajectory and then also about like getting sober.

[D]

So I, I had a pretty traditional, like first three decades of my life. I went to law school and bec a lawyer and then had a bit of a quarter life crisis around age 31. And when I was sort of on the cusp of making partner at my law firm, decided that I really hated that idea and so did my equivalent of joining the circus, which was to run away and become a professional poker player. Did that for like three years. It went very well. I had a lot of fun doing it. And then I had like the, the transition basically is I started getting really into various psychedelic substances for like, mind expansion purposes. Had a radical spiritual experience in the course of using those drugs. And that was kind of like the door that opened and led to a lot of compulsive drug use, a lot of compulsive seeking of that. That was the end of my poker career almost overnight and led to about three and a half years of really intense drug addiction, which I emerged from five and a half years ago after many, many attempts to get sober, was finally successful. And the book is. Is to some extent like the set of tools that I developed for climbing back out of that hole of being like very low agency in my own life, really unable to sort of operate in the world in a way that just wasn't using drugs constantly and sort of re ascend some kind of spiritual ladder to the life that I have stay, which is like really fun, really fulfilling, full of great relationships.

[C]

Yeah, I mean, what a turnaround. So like you've really been through it. To what do you credit the most for helping you find your way through?

[D]

The honest answer is like, Grace, um, I, I think many addicts have the experience of trying for a really long time to get sober, it not working, feeling like they are unable to recover. And then for some reason at some point you just get it and you are able to take the actions necessary to get sober. I think in the Popular imagination, this corresponds to a rock bottom. But in my experience, there are so many rock bottoms on the way down. Like, you hit a lot of things and you're like, maybe this is the rock bottom.

[C]

Nope, nope, nope.

[D]

And so it is kind of a mystery to me, even having recovered, why it was that I was able to finally take this step to, like, go to rehab, which was really what was necessary for me, spending two months in an inpatient facility. But that was sort of like the decisive action that kicked off this course of recovery. And then it was just like a slow process of participating in my own recovery, participating in recovery programs, and simultaneously trying to slowly rebuild a life. I think that I had pretty modest aspirations at the point at which I emerged from rehab. Certainly would not have anticipated anything like my current life, which is totally awesome. But there was this sort of, like, series of steps that I needed to take in order to, you know, become employable again, become solvent again, all of those things. And a lot of what's in the book is just sort of like the concrete things that helped me to do that.

[B]

So, you know, a lot of what you talk about is how people can, like, stop feeling stuck, right, and take that agency. So what is the very first thing you suggest someone do when they feel stuck in some aspect of their lives?

[D]

So I have this. I have this mindset that I discuss in the book called the crisis manager mindset. And there are a lot of different people who've hit upon essentially the same idea and just use different words for it. But the one that I came up with in addiction was sort of like this alter ego that I had, which was like, somebody who was being parachuted into my life, who was not responsible for whatever had come before. So it's just like, oh, you are in charge. You're the crisis manager in charge of figuring out how to clean up this wreckage of a life. What is the first step that you will take in order to do that? And I think it can be really easy when you are stuck to focus on the fact of your stuckness, to focus on especially points of prior freedom where you're comparing yourself to how good your life used to be, and unlikely it is that you're going to be able to, like, recapture the promise that you once had. I think that kind of thinking is really, really common. And the idea with the crisis manager frame is just like trying to sort of impose a cut in. In time in your life and say, like, whatever came before, like, you, this alter ego, are not responsible for that. You are only Responsible for, like, taking the next best action that comes in the future. And I found that to be really helpful, actually. Really necessary for me to start, like, putting steps and days together.

[C]

Yeah, I like that because it just seems like, you know, we all have this negativity bias and can be really hard on ourselves, right. So just freeing yourself from the past and any. Any shame that we might feel about the past makes total sense.

[D]

I think, like, one of the hardest things, like, one of the things that keeps people most stuck in life is this feeling of comparison not just to people around us, but to our past selves. And that's like, for many people who are trying to recover from addiction, that is the really intractable thing. And that's kind of like the final boss that they have to confront in order to recover.

[C]

Occasionally in our you ask, we answer episodes, like, when we get mailbag from our listeners, we'll have questions about how to best support loved ones who are going through and fighting addiction or serious depression. How do you feel like your loved ones best supported you in a way that maybe could be prescriptive for the rest of us who have those people in our lives who are suffering with addiction?

[D]

I really wish that I had a good answer for this, but, like, my entire experience has pointed to the fact that there isn't really a good answer to it. Like, as difficult as it was to be in the position of somebody who was trying to recover from addiction, I think it was even harder for the people who loved me and who were totally powerless to do anything about it. I think that, you know, you can provide all the support in the world, and it's great to do that when asked. But ultimately, like, you cannot give somebody else the will to recover. And that is sort of the. The irreducible requirement of getting sober. And so I. I don't have great advice for people who are going through that. I mean, I think, like, joining support programs for people who are in that position, following the advice of those support programs. I think it was great when my parents started drawing boundaries about the type of help they were willing to supply for me simply because it made things better on them, not because it was helpful to me, because I was beyond help. But, yeah, unfortunately, I wish that I had a more helpful answer to that, but I just don't know if there is one.

[C]

No, I appreciate that. That's. It's very honest.

[B]

I want to talk a little bit more about some of the strategies in the book, particularly this sort of broad idea of getting over the fear of rejection and you talk about the moat of embarrassment because you define what the mode of embarrassment is and also talk about why rejection sensitivity in particular is so, so important when we're talking about agency.

[D]

So there's, like, two closely related concepts. There's. You have to have little cute little names for everything when you're writing a book like this. There's the path of least embarrassment, and then there's the mode of low status. And they are. They're, you know, overlapping concepts. So the moat of low status is basically like. It is probably theoretically possible for you to become good at a lot of things if you put the effort into doing it. Um, but often in order to really get better at something, you have to allow people to see you being bad at it because it's hard to improve in isolation, only working in theory instead of in practice. And so, like, if you want to become a better dancer, theoretically, maybe you can, like, set up a mirror in your room and watch a lot of YouTube videos, but, like, at some point, other people have to see you dance, or you have to dance with other people.

[B]

People.

[D]

And that. That fear, even if we think that it's, like, temporary on some level, knowing that people will see us being bad at something on the way to becoming better at it is just really, really excruciating for most of us. And I think. I think part of why this happens is, like, it's easy to conjure up the feeling of being embarrassed by something because those memories are so salient for us. Like, it's easy to remember the time that you were made fun of at the school dance for being a bad dancer. That was from my life and, like, just how humiliating that was. There's no, like, equivalent salient memory of, like, gradually achieving competence or mastery at something, you know, and so there's, like, nothing on the other side of the scale. And I. So I think it's like, it's really hard for us to actually envision the end state of being better at something and sort of enjoying that. And really easy to imagine the displeasure and embarrassment of temporarily being bad at something in front of other people. And that, like, asymmetry keeps people from crossing this moat.

[B]

And what happens when we cross the moat?

[D]

Often we are genuinely embarrassed. But then it gets better. I think a big theme throughout this book is trying to disabuse people of the idea that if they think the right set of thoughts, they can cure the experience of embarrassment or avoid it altogether. So with. With failure, with rejection, with embarrassment, I think you can either try to think your Way into a different type of acting in the world. If I just apply this one mental trick, then I won't feel scared of doing this thing anymore. And I think that almost never works. Or you can try to act your way into better thinking, which is you just do the thing anyway. You experience the embarrassment and experience the fact that it is actually not nearly as bad as it is in your imagination. Like, sometimes things are a little bit embarrassing, but, like, you're now an adult. Those feelings don't linger. You don't have to take them on

[E]

board

[D]

as a pointer of your own badness or inadequacy. In some larger sense, it can be kind of confined. And I think that, like, with habituation. Yeah, you can really, like, learn to not feel these things so deeply. And so, like, getting practice, being embarrassed, getting rejected, getting practice with failing, I think is like, really one of the core messages of the book.

[C]

Yeah, it reminds me of one of the most popular TED talks of all time. And it's this guy who basically spends a year trying to get rejected every single day in one way.

[D]

He's in the book.

[B]

Oh, okay.

[C]

Okay. Yeah, Yeah. I just remember his name was Ja. And it had such a lasting effect on me because I feel like. And it. I also read a book before my first child was born about babies and, like, the genius of babies. And one idea that really stuck with me actually correlates with your work because it's about how often babies fail in a single day on their way to learning how to roll over, on their way to learning how to sit up, on their way to learning how to stand up, on the way to learning how to walk. And the reason why they have such tremendous growth is because of their willingness to fail as much as they do. And so, for me, it sort of removed a lot of barriers in my own thinking about just perfection and trying to be good at things right away, or I only gravitated towards things that were easier for me and not towards things that were harder.

[D]

I had. I had the same thing. I had this, like, belief that not only was it important for me to be the best at something, but it was important for me to instantly be the best at something. Like, there could be no. No, like, learning curve whatsoever. And it's so. It's so silly to, like, say it out loud, but it also exerted such a huge psychological effect on me for, like, most of the first several decades of my life. It was just intolerable to me to, like, think about being bad at something, let alone allowing people, Other people to see that I was bad at something and that. Yeah, I mean like that really limits your growth if you can. The further you can get away from thinking that way, the more you can be back in this like baby mindset where you're actually learning so quickly because you're constantly getting feedback from the world.

[C]

Okay, let's take a break and we will be right back.

[B]

I feel like if months were days of the week, then August would be Sunday. Does that make sense?

[C]

Oh, because everything is starting again in September.

[E]

Yeah.

[B]

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[C]

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[A]

Guessing is for game shows, not your business. Workday is the enterprise AI platform for HR finance and it with AI grounded in your context to get work done and done right. It's a new work day.

[B]

How do you suggest people with like ADHD who, you know, rejection sensitivity is kind of built into that diagnosis. Like is there something that they should do differently or you know, how can they kind of adapt what you're saying to help.

[D]

That's interesting. I didn't actually realize that rejection sensitivity was, like, a particular part of that. Can you say just, like, a little bit more about that?

[B]

Yeah, I mean, it's. People with ADHD have higher rejection sensitivity. That's. That's kind of, you know, so it can go so far as to, like, they don't like to call people on the phone because they don't want to. They don't want to, like, bother them. And, you know, just reaching out to people about even, like, hanging out is really hard. And that's like, on a social level and then on a professional level, obviously, you know, applying for jobs or networking, working or, you know, anything like that is just. It's just very difficult. I mean, I'm not a. I'm not a clinician, so I don't, you know, I can't really speak to why that is part of the diagnosis, but it. It is. It is part of adhd.

[D]

That's so interesting. I. I've been diagnosed with adhd, and I also have a lot of the behaviors that you just described. And so I never, like, connected those things, actually. But, I mean, I can remember as recently as, like, let's call it eight years ago, before. Before my addiction really kicked off, like, not wanting to call room service at a hotel where I was staying because, like, the idea of talking to somebody and placing an order was just, like, crippling. So I would just, like, avoid that. And a really intense fear of, like, inconveniencing people in any way because it was, like, an opportunity for them to say no or feel put out by me. So I guess, like. Like with the. The background that these are really familiar dynamics from my perspective, I would say, I think that the techniques will. Will work too, for people who have these things.

[B]

I.

[D]

It. It's like, kind of surreal to me now if I try to put myself back in the mindset of somebody who had that level of fear around everyday things to, like, know the. The shape of my life now and just, like, the fact that that doesn't enter into my mind. And I think so much of that just comes from habituation. Yeah, yeah. Like exposure, getting rejected a lot.

[C]

Yeah. Just go for it.

[B]

And seeing that your, you know, life

[D]

goes on, nothing happens, it's like, yeah, yeah, that's a lot of it.

[B]

Yeah. My husband has adhd, and that has been a big theme, you know, throughout our relationship. And I think at first I wasn't super, like, sympathetic to it because I was like, just pick up the, like call the, call the pharmacy for your meds. Like, why is this. You know, and it. But it really was like really hard for, like legitimately hard for him to do. And just, you know, a lot of the things that you're describing were really difficult. So. Yeah, I don't know. I was thinking of that when I was reading your book. So.

[D]

So interesting to me. Just, I never, I'd never connected those things.

[B]

Yeah. So maybe this will, I don't know, open up something else for you. Another thing that I just, I wanted to touch on briefly is one of the things that you talk about is increasing your surface area for luck. And I was just reminded of this talk I went to once when I was in journalism school by Bonnie Fuller, who was like, you know, a major celebrity magazine editor in the. In the aughts and ot teens. And she had this whole, her whole them making your own luck. And at the time I was sort of like, okay, like you're kind of full of shit. But like now I'm kind of seeing how this mindset is kind of powerful. Right. And so I'm wondering if you could speak a little bit about this. Like, how can you start to increase your surface area for luck and what does it do for you?

[D]

Yeah, I think this just comes from like an observation that it's really hard. Steve Jobs has a quote, had a quote that I like, which is it, you can't plan to meet the people who will change your life. And I've found it to be the case that like, with most of the interesting things that I have done in my life, I can trace them back to encounters that were basically chance encounters. Like I just happened to have a conversation with somebody who shared an interest with me and something like came out of that. That's how my last several jobs slash companies have started. And so I think the idea here is basically like for any given interaction that you have with somebody, there's some probably low chance that something will come out of that that will significantly change your life. And so you just want to give yourself a lot of chances to get lucky. Basically, like take a lot of shots on goal is like an analogy that people like, if you have a, A, a low percent chance of making the goal, but you take a lot of shots, like sometimes they go in. And so increasing your surface area for luck is basically just like creating opportunities to encounter a wider range of people and more of them. And I think there are like all sorts of ways that you can go about this. A lot of them involve in person stuff. But for those of us who are socially more reserved, I also think that just writing on the Internet is a huge one. And a lot of interesting stuff that has happened in my life in the last few years is downstream of stuff that I've written on Substack. Like that's how I got my last job. It is how I'm in a position to like, work on the thing that I'm working on now, which is a new company. It is something that works surprisingly well for people even when they're starting without a large following. Because it's sort of like this. It creates opportunities for people to self filter according to whether they have something like, interesting to interact with you about. So, yeah, it's just. It's just a matter of like taking more shots on goal. Yeah. Having more shots to get lucky. Yeah.

[C]

Tell us a little bit about this company you're starting.

[D]

It is basically a. It is a financial and philanthropic services organization for people who are. Who have made money from AI. So a lot of people who work at the big AI companies have high philanthropic intent. They want to give away a lot of their lifetime wealth. And there's not a good mechanism to do that for sort of like esoteric reasons that have to do with how money moves through the system. So that's like the core idea of it. Okay.

[C]

Okay. Interesting.

[D]

It's actually related to the last thing that I did, which has never before been the case in my life where I'm actually just like building on prior experience or relevant expertise. Yeah.

[B]

Do you still play poker?

[D]

I basically never play. I play it. I'll play with friends every few months maybe, but like in a $1, $2 game, max. I actually, when I was. I had a little break from work when I left my last thing before I started this new thing and I went and played a little tournament series at the local casino and that was really fun. I have in the past suffered from the effect where if you are like, used to be good at something and now you're no longer good at it, it sucks extra hard to do it because you can feel the gap between the two. But I think I've now crossed some threshold where that doesn't pain me so much anymore. And it's just like a totally new thing. And I really enjoy playing poker from

[B]

that perspective as someone who will never be a professional poker player. It is, it is. I don't know, it's just, it's very cool to me that you did it for even, you know, as long as you did so thank you.

[D]

It was a great. It was a great thing while it lasted, and then it ran its course.

[B]

Yep, yep, yep. Well, I actually did want to hear a little bit about how, like, what. What you sort of took from poker that you applied to the rest of your life.

[E]

You.

[B]

You have some examples in the book, but if you could just kind of share.

[D]

Yeah, I mean, I think that there are, like, there are a number of ways of thinking that I learned in poker, like, specific ways of viewing the world. So, like, an example that comes up in the book is like, thinking in terms of expected value instead of a mindset where success is what matters. So to make this more concrete, if you play tournament poker, which is what I did, you lose almost always 10 to 15% of the people who enter a tournament will make any money at all. And most of them will not make very much much. And so your tournament life is like long series of losses punctuated by occasional big wins that more than make up for the losses. And the question is, like, what kind of person wants to do this for a living? I think that's a good question regardless, because it's a pretty hard way to make a living. But. But, like, thinking in terms of, like, if I succeed at this thing, the payout will be big enough to make up for all of the losses. I think this is a type of thinking that generalizes to other areas of life and actually really influences the way that you can think about your career, for instance, or probably, like, dating and lots of other things. This comes up. It's come up in my later life in terms of like, like doing funding work or philanthropy work. Writing a book is kind of a similar thing where most people who write books do not sell a lot of copies. They aren't very successful. But, like, every once in a while, somebody really breaks through with one funding company is sort of the same thing. And so this. This, like, mindset of as long as you are not actually risking everything, as long as you have some ammunition behind taking chances where you are likely to fail in any given situation, but where the successful event is, like, really, really good, I think that's something I've been super willing to do in my life since poker that other people are maybe less willing to do, just like out in the general population.

[C]

So, Kate hall, before we let you go, then the book is called you Can Just Do Things. What do you hope readers and listeners will do after reading the book or hearing this conversation?

[D]

So I. I think about agency as something that comes much more naturally to some people. Than others. And something that I've observed in the world is that people who are say, high and dark triad traits like narcissism or sociopathy tend to be more naturally agentic than other people, I think because they are like not rule followers by their nature. They're just a lot less concerned about embarrassment or what other people will think. And so my book, the dedication is to the best who lack conviction from the second coming poem. And the goal is to sort of extend the thinking behind agency to a wider group of people who are going to apply it in more pro social ways. The whole last chapter of the book is examples of people who are exercising their agency to do incredible things in the world. And my hope is just that more people who are currently concerned with following rules maybe become a little bit more selective about which ones they're following and a little bit higher in terms of the variance and the agency they welcome into their lives.

[B]

Lives.

[C]

Very cool.

[B]

I love that. Thank you, Kate.

[E]

Kate Hall.

[D]

Thank you.

[C]

Yeah, thanks so much.

[B]

Just before we go, where can our listeners find you?

[D]

You can find me on substack at Useful Fictions is the best place to do it.

[B]

Okay, great, great. Thank you. Kate was really great. I really liked her energy and just hearing about her life was. Was really fascinating. So I hope you all enjoyed our conversation with her.

[D]

I.

[B]

We are now in the intention zone. Last week I was talking about my word count. I have been pretty good about it. I haven't been. There were like a couple days where I wasn't able to do it, but I've been like pretty good about it. So I'm feeling good about that. And then this week I'm just gonna kind of focus on getting Henry ready for school. We did some school supply shopping. We did not do a haul video, but we did do. No, we didn'. We did, but you can put it on your TikTok. Yes, you're right. I could. Got him like all his school supplies and we got him a new desk at ikea. We still have to put that together, but it has been acquired. So just like getting him all set up.

[C]

Who's going to be doing the IKEA furniture assembly? Is it you or Matt? Not you. Okay.

[B]

I mean, I'm actually like not bad at putting together IKEA furniture, but like I would pre prefer to not have to do it. Right. How about you?

[C]

So last week I was trying to like get back into structure. Just like having some units of things that I did each week because I had been on vacation.

[B]

Yeah.

[C]

And so I got back to two units of like a class pass class of like a Pilates class or a strength, you know, like a lifting class. And then trying to do cardio at least once. So I, I got, I, I did it. I've done it for like the last two weeks and I don't know if I can keep it up, but I'm trying that. And then the other part of my structure was just to like read a little bit each night because I totally go on these like long reading binges on vacation.

[B]

Yeah.

[C]

But then I come home and I am not regular about it. I love it. And I'll, you know, I read most nights but not like, or most at some point during the day, but like not in a structured way. So I'm trying to just give myself time first thing in the morning or before I go to bed bed to do that. Like 10, 20 minutes. And then this week, and I don't know if maybe like I've just gained weight on vacation or something, but like a bunch of random, like I'm feeling my body kind of like feel a little creaky and achy in different places. And so I'm gonna work on. I don't know if I need to go to acupuncture or just do some like foam rolling and, or some PT or I don't know. But like, I just want to work out some of these kinks because I don't want them to become problems later. Yeah. But something is like a little bit off and I think it's an alignment thing. So, you know, I love my acupuncturist that I tried in the spring. So I'm gonna go back to her.

[B]

All right, sounds like a plan. All right, everybody, thank you so much for listening. Forever 35 is hosted and produced by me, Dorisa Freer and Elise Hu and produced and edited by Sam Hunio. Sammy Reed is our project manager and our network partner is Acast. Thanks everybody.

[C]

Talk to you next time.

[B]

Bye.

[A]

Guessing is for game shows, not your business. Workday is the enterprise AI platform for HR finance and it with AI grounded in your context to get work done and done right. It's a new workday this summer.

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