Cate Hall cashed more than $1 million playing professional poker, then spent three and a half years as a drug addict, before going on to run a $3 billion foundation.
Most advice for high achievers assumes they already know what they want. Hall spent almost three decades chasing prizes — competitive chess, Yale Law School, a partnership track at a Washington law firm — without ever asking herself why.
"I was a very narrowly success-focused person for a lot of my life up until around age 30 when I sort of took a turn off of the established college law school lawyer path."
Hall is the author of "You Can Just Do Things: How High-Agency People Get What They Want Out of Life," a former chief executive of the Astera Institute, a $3 billion foundation, and is now building a new advisory business for wealthy philanthropists — all before turning 42.
I listened to the full interview so you can skip it. 83 minutes of audio, 19 minutes of reading.
Here are the 12 takeaways that matter.
👤 Guest: Cate Hall, author of "You Can Just Do Things: How High-Agency People Get What They Want Out of Life" and former chief executive of the Astera Institute, a $3 billion foundation
🎙️ Host: David Deming, an economist at Harvard's Kennedy School who has taught effective altruism there for about ten years
📰 Published: 9 September 2026 on YouTube
🔴 YouTube | 🔗 Show notes | ⏱️ 1 hr 23 min | ✅ Time saved: 1 hr 4 min
Key Takeaways
She decided in sixth grade to stop trying to fit in and just win every game there was
She calls it a dissociative coping strategy, not agency, and says she was "incredibly awkward"
Staring into the abyss means asking the questions you already know to avoid
The exercise: list your avoided questions, or have an LLM generate them, and look for the one that produces dread
She used the exercise on her own vaccine startup and concluded it shouldn't exist
She wound the company down and fired the staff rather than become its sole CEO
She chased Yale Law's top grade with no idea why, and no memory of choosing law school at all
Six years at a Washington law firm ended after LSD forced her to confront her own boredom
She used psychedelics after reading a Johns Hopkins study on the drug easing terminal cancer patients' fear of death
Her edge in poker, where she cashed over $1 million, was reading physical tells, not math
She suspects she and two friends who shared the obsession were all undiagnosed autistic adults
Most organizational structures are built to suppress agency until you reach the top
A "boring, stupid life" scared her into recovery more than the risk of dying did
A psychedelic experience gave her what she calls private proof that God exists
She was a self-described dogmatic atheist from age five or six
Her new business does the "schleppy" work — setting up trusts and utilities — that multifamily offices avoid because it's low status
Philanthropy underuses recoverable grants and loans that could put capital back to work
Marriage constrained her present self in service of a more agentic future, not the reverse
1. Deciding To Become a Machine
Deming opened by asking whether Hall was a high-agency kid. She said no — she was a "weird kid," which she distinguishes from having agency.
She was good at winning whatever game she was playing, without examining why she picked it. "I didn't really think very hard about the way that I picked the games that I played, and as a result, my life was just sort of a string of I will do X activity for a while, I will achieve something in that activity, then I will hop onto a different ladder."
She played competitive chess and violin, and her grandmother taught her cards
A string of social disappointments around middle school produced a resolution to opt out of human relationships entirely. In her own recollection of the moment: "I will simply win every game there is to win"
She describes herself at that age as profoundly awkward. "As I said, I was a really weird kid. You might not know it from talking to me now, but I was incredibly awkward, incredibly awkward." Looking back, she now suspects she was on the autism spectrum
She rejects calling that decision high agency. "It was, like, dissociative" — a coping strategy for fleeing discomfort, not a deliberate choice
She attended the University of Arizona for money, after being admitted to better schools, and pushed herself to outperform students at those schools instead: "I had an attitude of I have to make sure that I don't fall behind what people at better schools are doing here."
She double-majored in biochemistry and philosophy, edited the student newspaper and published lab research, all while unhappy: "It was just very, like, I will march to the top of this mountain"
Asked if she was happy in college, she said no. Her first happiness, she said, "comes, like, in my late 20s"
Her advice to a young achiever chasing prestige is that the shortcut doesn't exist. She said the same wisdom is available to any 18-year-old and gets ignored anyway, until it is earned firsthand rather than heard
Watching high-agency people in action taught her more than being told to be one. Her example was her high school AP chemistry teacher, who let her copy answers straight from the answer key rather than force her to learn the material — a lesson in that the choice, and its consequences, were hers alone
2. Stare Into the Abyss
Hall credited the framing to her friend Ben Kuhn: certain questions "lurk on the edge of our awareness" that people avoid asking because they don't want the answer — whether they chose their major for themselves, whether they're in the wrong marriage, whether they built a career around the wrong thing.
The exercise is to surface those questions and sit with them honestly. She calls it "a form of extreme self-examination"
The test for whether you've found the real question is whether it produces dread. Her instruction: come up with your own list if you can, or — if you can't — read a prepared list of candidate questions and watch for the one that makes you flinch
An LLM can generate that list for you when self-generating it fails. She said outsourcing the question-generation to another person or a language model can "short-circuit" the internal process people use to avoid noticing their own hardest questions
She did the exercise herself while writing the book and found something she wasn't willing to share on camera
Shutting Down Her Own Startup
Asked for an example of the exercise in practice, Hall described co-founding a startup making shelf-stable vaccines during the pandemic, at a time when cold-chain storage was a real bottleneck.
About two years in, the original business plan had stopped working, and her co-founders elevated her to co-CEO to lead a pivot. She then ran the abyss exercise on the decision and reached an unwanted conclusion: the business itself shouldn't exist
She wound the company down and laid off staff rather than take the CEO role. "I think it was very clearly the correct decision," she said, despite how bad the decision felt to make
Her reasoning was that the venture, while viable as a business, wasn't remarkable enough to justify the group's original ambition. "We'd all kind of gotten into it with the hope of doing something that was really super valuable for the world at large instead of just, like, something that would make money"
Everyone let go went on to other high-impact roles, which she frames as liberation rather than failure
She argues that a genuine conflict between your interests and other people's is rarer than it feels in the moment. "The number of situations in which your interests are genuinely misaligned with other people's is not that high." She said she expected the layoffs to be catastrophic for the people involved, and instead "it was just fine for all of them"
She extends the same logic to relationships she was afraid to end, on the premise that people are more resilient to disappointment than the person delivering it expects
3. Skip the Movie Dialogue
Hall's second piece of advice from the book: stop communicating the way characters do in movies, where drama is manufactured by people who refuse to say the obvious thing to each other.
Her example is La La Land, where an entire relationship falls apart because the two leads never have a direct conversation about their conflicting plans
She thinks the pattern is more than bad fiction — it's a bad model for real life. "To the extent that life imitates art, it's really dangerous," because most everyday tension can be resolved simply by naming it out loud
Deming, who has two teenage daughters who watch romantic comedies, said he narrates the plot from the couch — "why don't they just talk to each other" — to no appreciation from his kids
The reason people avoid direct conversation, in her view, is fear of the other person's reaction, and working around that fear creates more effort than it saves
She points to Kim Scott's "Radical Candor" as a guide to doing this well, and adds a caveat: the advice to be direct assumes both people are emotionally healthy and negotiating in good faith
Deming added that going first — naming your own part in an awkward moment before asking the other person to — invites more candor back than waiting for someone else to open up
4. Grades With No Reason
Hall could not recall why she chose to go to law school at all — only the moment she got into Yale.
She remembers the acceptance and nothing about the decision that preceded it. "I cared so much about getting into Yale Law School because it was the biggest prize that I had in front of me. And I remember just like weeping with joy that I'd gotten into Yale Law School." She says she has no memory of why she chose law school in the first place — only of getting in
At Yale Law, which doesn't grade, roughly the top 10% of each class still receives an honors mark instead — and she fixated on collecting them. "I was really obsessed with getting like all H's in law school even though there was no- nothing that it could've been relevant for besides getting into a slightly better law firm and a slightly better clerkship"
In hindsight she sees the years as wasted, since the credential bought her nothing she actually wanted. "I could have just spent three years doing stuff that I found interesting, graduated with all P's, had a degree from Yale Law School, and been on a completely different life course. But I never, I never considered that."
She calls the whole period unhealthy. "I think that I really did not enjoy it, and developed a lot of unhealthy coping mechanisms for that"
She traces the drive less to intrinsic motivation than to fear of what she lacked. "I would distinguish it from, like, intrinsic motivation and say it is more a matter of fear," channeling attention into the one domain — academics — where she knew she could win, rather than confronting the social domain where she felt exposed
She noted that other students at Yale Law chose the opposite path, doing what interested them since grades barely mattered, but she doesn't remember admiring either group as role models at the time
5. Six Years Bored, Then LSD
After Yale, Hall clerked, then spent about six years at a boutique Washington firm doing appellate work — and Deming quoted her own line back to her, that she was "the kind of bored that makes caged animals stop eating."
She says the boredom was constant, and what changed was that it stopped being a cost she was willing to pay. "I was always bored, and what happened was boredom stopped being acceptable to me as a cost"
A persistent, near-daily dread about her own mortality — not the boredom itself — was what pushed her toward psychedelics. "And I read this study, of people who were, who had terminal cancer diagnoses, at Johns Hopkins, who did LSD to deal with end of life anxiety, and it was really, really effective for them."
It worked for her almost immediately. "I think within a couple of times I just like stopped thinking about it and haven't really thought about it very much at all since"
The drug forced a reckoning she says she'd been avoiding. "Oh, this is not a life that I wanna have. I need to, I need to do something fundamentally different with my life," she recalled realizing, though it took another six months to a year to act on it by leaving the firm
Deming distinguishes agency from mere success or effort by whether someone questions what they're doing and why. "I think, from my perspective, a really key component of agency is questioning what you're doing and why."
Hall agreed the distinction is fair, and said quitting law for professional poker was, by that definition, a genuinely high-agency act — even though her life up to that point had felt directionless
6. Reading Faces For a Living
Hall played poker full time for about three years and cashed more than $1 million.
Raw computation put her in the top 5% of players, by her own estimate, but that wasn't her real edge. "Most of my edge though, and most of my results came from totally falling in love with the aspect of poker that is reading people's body language" and physical tells
Deming connected the skill to his own research on soft skills: a psychological test called Reading the Mind in the Eyes, developed by Simon Baron-Cohen, trains people with high-functioning autism to consciously decode facial expressions that most people read intuitively
Hall said that description fits her exactly. She and two friends who shared the same obsessive study of body language later realized all three were likely undiagnosed high-functioning autistic adults who "carefully studied what people were doing" rather than absorbing it automatically
Other players dismissed the skill as invented. "That's bullshit. That doesn't exist. You're not doing that." — a reaction she found bewildering until she realized people who read faces intuitively simply can't perceive what she was doing explicitly
Beyond reading opponents, she came to love manipulating what they saw in her. She learned to send false signals deliberately — a tactic she says works well against amateurs and not at all against professionals
Bureaucracies Kill Agency
Poker was the first time in her life she worked for herself rather than inside an institution, which raised the question of whether agency is possible inside a large organization.
She thinks it's close to impossible in most hierarchies. "I think it's really hard to live in a big hierarchical bureaucracy and to be high agency. I think most organizational structures are designed to discourage this."
She ties this directly to career dissatisfaction in fields like law, consulting and finance, where reaching a position with real control over one's own path takes years
Both agreed that organizations concentrate agency at the top and require most people to suppress theirs to get there — and that for some people, she said, it never fully returns
7. Three Years as an Addict
After an intense, unplanned spiritual experience during early drug experimentation, Hall says addiction consumed roughly three and a half years of her life.
She doesn't fully know why her final attempt at recovery worked when earlier ones didn't. "It is the experience of most addicts who have recovered that they have, … Like I tried many, many times to recover and I hit many different bottoms along the way." She says most who succeed can't explain why that particular time was different
She eventually committed to a 60-day stay in rehab, and it held. "I just had finally a, a moment, like a series of realizations that prompted me to tie myself to the mast of rehab"
What motivated her wasn't fear of death but fear of a small, boring life. She said continuing on her path meant risking not death, which she thinks she'd have accepted, but "a really boring, stupid life." "And that was the thing that was really intolerable to me," she said — the image of living with her parents, unable to hold a job
She argues that some amount of suffering is necessary for a meaningful life, though not as much as she went through. "I think it is very, very clearly not zero." She said overcoming adversity is a large part of what gives a life meaning, and that a one-year addiction rather than three and a half would likely have left her equally happy today
Hitting bottom, she says, gave her more freedom to reset than staying successful ever could have. Dropping to what she calls zero personal agency and rebuilding broke her out of an old assumption about what level of life was "appropriate," and having little left to lose, she said, was "kind of a luxury in certain ways"
8. The Moat of Low Status
Hall credited her husband and co-author, Sasha Chapin, with a concept she calls the moat of low status: effective learning happens in public, but most people avoid looking incompetent in front of others while they're new at something — so getting good requires tolerating the embarrassment of being bad first.
After rehab, she took six months to find any job, eventually becoming a personal assistant to a friend for little pay — work she says pride would have stopped her from accepting before addiction
She named a concept from addiction recovery for the same willingness: "gift of desperation." Being out of options, she said, makes people willing to do things not normally "on your menu of options"
A conversation at a party about biosecurity became her way back into a career, and she deliberately built out the network from there — mapping the field, seeking introductions even when uncomfortable, in what she described in the book as increasing her surface area for luck
She expected to be turned down often and mostly wasn't. "Much less than you would think," she said of the rejection rate — though she acknowledges that "having gone to Yale Law School, having been a top poker player, like, it did make me, higher status than the average recovering drug addict"
Deming added that people are unusually responsive to genuine curiosity and a good-faith comeback story, and that students who stumble and turn things around get more grace than they expect
She stayed selective about what she disclosed while rebuilding. "I definitely did not tell people that I was a drug addict in my first years after recovery." Her own summary of the approach: "So some candor but not too much."
9. A Late, Sudden Belief in God
Hall's book ends with a line thanking God. She said the spiritual experience she referenced earlier — mediated by psychedelics — amounted to private proof of God's existence that she has never been able to convey to anyone else.
She was raised by non-religious parents and describes her younger self as dogmatically atheist, despite being the child of a minister. She recalls thinking, at five or six years old, "Isn't it funny that humans invented this lie about God?"
The conviction from that experience has not wavered through addiction or recovery. "I have a really deep belief in the existence of God, in the goodness of God, and in the fact that there is, like, a meaning and a purpose to the things that we go through"
It replaced a much darker prior worldview. She describes her earlier self as chronically depressed, believing "the world is bad, people are bad," with no larger consequence to any of it
She reconciles agency with religious surrender by treating agency as a way of giving God more chances to act. She frames it as "generating a lot of energy" to create more opportunities "that God has to work in my life," since God works through people
She said her eventual destiny is a monastic one — retiring from active work to focus on prayer and contemplation — but not yet, because she still feels there's important work to do
10. Maslow, Then a New Business
Deming raised Maslow's hierarchy of needs — esteem, then self-actualization, and a level Maslow added later called self-transcendence, or serving something larger than yourself — as a frame for Hall's arc from achievement to service. She agreed the description fit, and it led her to describe, for the first time in the conversation, her new company.
The business helps very wealthy people manage their lives and philanthropy so they can be, in her words, the most effective versions of themselves. She calls it fundamentally service-based: extending herself toward the goals of people whose values she endorses rather than pursuing her own
It sits in a category called a multifamily office, but reaches a different kind of client than a typical single-donor foundation. Most multifamily offices, she said, would rather do investment management and treat philanthropy as an add-on because it carries its own status
She spends real time on unglamorous tasks other firms in the category avoid. "Let me research all of the trust companies and find a professional trust manager for this person and, like, set up their utilities" — work she calls low status and says she genuinely enjoys, while also arguing it makes her a better leader because she stays close to the details
The company started as a new kind of donor-advised fund and grew broader from there, adding both life-management and wealth-management services that go beyond philanthropic funds alone, in response to what clients actually wanted
11. EA's Blind Spot
Hall said effective altruism, in practice, has focused far more on choosing which causes to fund than on the mechanics of deploying the money well — which is the gap her new business is built to fill.
She said the same split shows up across all of philanthropy, not just EA. The two ends are grant-making — which she calls "the philanthropy from my childhood" — and separately, endowment management or financial operations, with too little use of instruments that blend financial return and philanthropic impact
At her prior role running Astera, a private foundation, she used recoverable grants, loans and loan guarantees that acted as credit enhancements for project finance — tools that let philanthropic capital be reused rather than spent once
Philanthropic dollars increasingly flow into venture funds rather than foundations, which she called a recent shift and only one of many instruments the field could use more of
Both agreed EA's hardest critique is that it favors what can be put in a spreadsheet over what can't. "I think it is a fair response to EA in general that it tends to overemphasize the things that can be clearly quantified, and put in a spreadsheet" — problems like national corruption or weak institutions resist the same kind of measurement that bed nets or vaccines allow
Neither treated that as disqualifying. Deming argued the field, fifteen years old, is already extending into harder territory like criminal justice reform; Hall said she doesn't experience the limitation as criticism so much as an open question of how to extend the framework further
12. Marriage as Agency
Deming proposed that marriage and commitment are an exercise of present agency used to constrain a future self. Hall pushed back on the framing.
She sees commitment as building future agency rather than trading it away. Her early marriage to her husband was difficult, and taking the option to leave off the table reduced her agency in the moment — but she says it served "a future of deeper connection," a more meaningful life with greater agency overall
She argues people generally function better under constraint than without it. "I think, a funny thing about humans is that they tend to operate under conditions of restraint much better than unbounded conditions"
She credits the structure of marriage itself with progress she doesn't think would have happened otherwise. "I feel like the place where I've gotten in my relationship with my husband would not have been possible without the forcing function and constraints imposed by marriage"
Asked what she'd hope to be doing a year from now, she described the remaining stages of her life as years spent in service to others not tightly bound to her own ego — "and then, you know, retire to the monastery after that"
Bonus Insights
She distinguishes exposure to high-agency people from being told about agency. Reading advice, in her account, mostly bounces off; watching someone else actually operate that way is what changes behavior
Deming noted that the internet now gives young people a substitute for the in-person exposure he had only through classmates and professors at the University of Arizona — a way to find like-minded people regardless of where they physically are
Hall's own account is that her worst years — the boredom, the addiction, the three-and-a-half-year detour — did more to teach her what she actually wanted than any of the credentials she collected on the way up, and that the business she's building now is an attempt to put that back to work for other people's money rather than her own ambition.
Products, Companies & Tools Mentioned
Astera Institute (The $3 billion private foundation where Hall was previously chief executive, and where she used recoverable grants and loan guarantees rather than pure grant-making)
Books & Resources Mentioned
You Can Just Do Things: How High-Agency People Get What They Want Out of Life – Cate Hall (Her own book, the subject of the conversation)
Radical Candor – Kim Scott (Hall's recommendation for how to frame direct conversations well)
Reading the Mind in the Eyes test – Simon Baron-Cohen (The diagnostic tool Deming cited for training people to consciously decode facial expressions, which Hall said matches how she taught herself to read poker opponents)
Kegan's stages (A model of adult psychological development Hall referenced when discussing whether there's a "true self" waiting to be discovered)
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