Last week, in part one, Leah Sargeant shared how her household was formed and what keeps it running. In part two, we discuss work, AI, how Eliezer Yudkowsky helped Leah convert to catholicism, and what keeps us human.
A Random Walk Across Careers
N: I would love a brief overview of your work.
I’ve held a large number of jobs, in what you could describe as a random walk across careers — it’s very hard, looking at whatever job I held at time point N, to predict what job I will hold at N+1. If anything united these jobs, they’re interesting, and hopefully high-impact. For me, changing jobs is often about picking somewhere where I’m going to learn something new, or need to acquire mastery of something. Whatever job I take has to be compatible with hosting book clubs and debates at my house, and spending a long time working on my Halloween costume every weekend.
N: Do you have a Halloween costume right now?
My Halloween costumes are less ambitious with kids because if we’re doing group costumes, everyone needs to be bought in. People are not reliably bought in until 2–3 weeks before. So you’ve got to be scrappy and adaptable. I really ticked off my eldest the year I was “Diotima’s Ladder of Love” because she felt a ladder was not a real costume. Before I had kids and marriage, I was only looking for jobs that allowed me substantial slack outside of work, or flexibility. I had a lot of practice looking for jobs that were more family-compatible, or negotiating to make them family-compatible. Having weird, intense hobbies now means you will safeguard a work habit that will work for you when you have kids later.
For the Center For Applied Rationality (CFAR) specifically: I had a totally pointless internship while I was in college — I won’t name which state office it was in. There was an internship program, but no one was really in charge of making sure interns had tasks. During that period, I read the Sequences on Less Wrong. I was at one of the earliest CFAR workshops in California. A lot of tours through cognitive bias are about, “Here are all these things you do wrong — try not to do them,” which is hard and implausible. CFAR was like, “Here are things that people tend to do wrong in these circumstances. Be proactive about not being in those circumstances, or figure out what can counterbalance when you’re there.”
I had a lot of fun at the workshop. I went shortly after I knew I was converting to Catholicism. I found that Eliezer Yudkowsky‘s writings really helped me in doing that — in part because they’re about how you think seriously about the chance you could be wrong about something important: something that’s so woven into your view of the world that it’s hard to untangle what your premises are — and how do you conduct yourself as a person of integrity who prefers the truth to your current life?
Then I did some consulting work for CFAR, helping flesh out their curriculum on thinking in the Bayesian way in everyday life. I was working with Eliezer on that, and I enjoyed it so much, I began talking more to CFAR people, and I said pointedly, “This is such fascinating work. I only wish there were a way for me to give my full time to this challenge.” They brought me out for a work trial and ultimately offered me a job as a curriculum developer.
I really liked the work, but I hated living in California: far from my family, no good; only one kind of weather, bad; no housing in Berkeley, quite bad. People in California, and in the rationalist community, can veer too far into bringing their whole self to work. I have never wanted to do that. CFAR was cool work with cool people, and for some people this sense of, “How do you think critically about your life?” led them to blur lines between their work life and identity and the whole rest of their life in a way that wasn’t super healthy.
N: How did you then transition to policy roles, and now your work at Institute for Progress (IFP)?
I think of my work at FiveThirtyEight as part of my transition, because it meant reading policy more closely and trying to figure out, “What will this do in practice?” — which was really helpful when I became a policy wonk later. My very first job out of college was a policy wonk job at the Pew Charitable Trusts working on consumer banking reform, though I was at the very low data-scrubbing level.
Then I worked at Niskanen on family policy. I saw the job opening because I was already following their research — it was so good. They really cared about the details of design, not just the headline — “We’re doing this for families” — but will it work? Which families will the way you’ve designed this break for? How does this mesh with other programs? Not everyone in the policy space double-checks the discrepancy between the headline and the implementation. In a partisan environment, only your enemies will check your implementation details, and you don’t trust them to do it. A player like Niskanen, that genuinely cares about getting things right and telling the truth to anyone, has a huge value-add.
My biggest project was working on a proposal — which have now been introduced as a bill — for a newborn credit: money that would go to parents right after birth, when you need it most and it goes furthest; that you can use for diapers, to be able to take your unpaid Family and Medical Leave Act leave that you might otherwise have to pass up — to make that transition a little easier.
[At the time of our conversation] I’m partway through my second week as editorial director at Institute for Progress. Once again, this is a job and think tank I found because the work was so good. It had this family of people who care about the details, who are into questions that aren’t automatically in the news — because no party has claimed ownership of them — and are doing high-impact work. Both Niskanen and IFP are think tanks with a strong sense of humility — a real curiosity about, is this actually helping, and do we have real traction here? If we don’t, we shutter this project. Not, “It’s a big part of our identity to have this project,” or, “We’re not making any progress technically, but we’re on all the panels and everyone knows this is about us.”
The Cheapest Thing to Grant, the Most Valuable to Get
For a period while I was having kids, I was working mostly remotely. Accidentally in one case: it was more of an in-person job, but it was during the pandemic, so it became not very in-person just around when I had my first delivery. After that, I had a fully remote job for two years, with a lot of flexibility on how I set my schedule, which meant it was easy to have my babies at home with me. For some of those, I was working three-quarters time, which gave me more flexibility to have a work schedule that fit with my baby’s schedule.
Going to Niskanen was going back up to full-time. They were excellent. When I had my baby, I got to stretch out how long it was before I went back to the office. When we reached the day that we all thought was a reasonable day, and I hadn’t gotten my baby to take a bottle yet, my boss unilaterally extended it until I could get that to work.
At IFP, when I was negotiating for the job offer, one of the things I asked for was, “Can I start part-time until my husband is done grading for the end of the semester? That’ll make it easier for me to start sooner, so that my family has more slack.” They thought about it and said yes. People usually think about negotiations about salary and benefits. But non-salary things, especially temporary ones like, “Can I work part-time for three weeks as I get started?” are the cheapest thing for an employer to grant, and the most valuable for the worker.
N: Will you walk through how you’ve chosen positions based on your family?
Two times where I was going through an interview process while I was pregnant, I wound up with at least two offers and picked the less demanding job — because I’d made it past the point where I’d had miscarriages. If things went the other way, I was more open to taking the more demanding job.
In one case it’s because one job was fully in person. I thought, “If it were earlier in my life, I’d pick this one. I don’t want it for right now if this baby makes it.” In the other case, I was turning down a job I thought was cool and high-impact, but they said, “It’s really important that the person who takes this has continuity in the role. We really want someone who’s fairly sure they can do it for three years.” I was like, “I don’t want to say yes when I’m not sure that’s true.”
I try to be straightforward about it — especially as I’ve become more senior. “I’m taking tomorrow off, because I’m chaperoning the zoo trip for my kindergartener.” Not just, “I have a personal day,” so it’s clear that I expect you, my direct report, may also do that some day.
N: I think that’s so encouraging — to be able to see that people are living a balanced life in the way that you might also aspire to one day.
You say that you’ve gotten a lot faster as a writer — that having kids is like working under four-hours-before-the-paper-is-due circumstances all the time. I’m always astounded by how many different pieces you have out. I would love to hear your practical tactics.
Part of it is having very low friction to writing down an idea. I use the app SimpleNote. As I’m thinking about something, or reading a book, I’ll copy a quote into SimpleNote and write down four sentences about it. This is a thing in a house with two freelance writers — we’ll come out of a movie, and I’ll say, “Alex, are you thinking of pitching on this movie?” Because I’ve got half a pitch. Then we divide up which piece goes to which editor. Capturing stuff and having it in the back of my mind — by the time I send the pitch, I’ve got a sense of the shape of the piece.
By the time I sit down, away from my kids at the coffee shop, I’m ready to start and write quickly. The brainstorming has already happened. I work in 20-minute Pomodoros. I know the standard is 25 and then a five-minute break, but 25 is too long. Twenty minutes I know I can fill. In three Pomodoros I can write an op-ed — about 1,000 words. Then I walk home. I like that I can walk to the coffee shop and back as a way of getting into the place where I’m writing, and then I return to the excitement and chaos of my house.
Life in the Third Oikos
A souped-up Google, not a buddy: how Leah uses AI at home — and why she’s bearish on how close the Third Oikos really is.
N: I would love to dive into life in the Third Oikos. The biggest thing I’m curious about is how you currently use ChatGPT or Claude for home-related tasks.
My modal use of Claude is as a souped-up Google: “I read something in the past year on this topic in one of these two magazines. What was it?” I also use it for things like: “Is it likely this is an ear infection? Will the modal pediatrician, after I go to see the very slow pediatrician, say, ‘Why don’t you give it three more days and then see what happens?’” That helps me triage whether “this is an urgent care thing.”
My husband and I go to Gen Con, the largest gaming convention outside of Europe. When you register, it’s got a very complicated system of ranking all the games you want to get into. I had Claude make me a visual interactive applet of what was on my wish list, make sure my preferences were consistent across the ordered list where I was dragging and dropping, where I could best list friends to help them get into games.
What I don’t really use it for is as a chatty thinking partner. The feedback I most often give Claude is, “You don’t need to end our conversations with another question to continue. If I want to know something and you tell me, I’m good.” I’ll ask if I want to know something more. “What do you think of the book?” is a question for my husband. We are not buddies here. I try and stay sensitive to avoiding that.
N: One of the core theses of this publication is that our post-industrial society — the Third Oikos, the imagination of this post-AI, post-digital-technology society — will enable production to move back into the home. I believe we’re at the cusp of this transition, so I also believe we have the power to shape it. What excites you about the next era of technology? What are the particular dangers to personhood and how we see our humanity?
I’m more bearish on how close we are to the Third Oikos, though I like some of the possibilities. Because it’s about more flexibility — not just you can do things from home — it’s actually very challenging to integrate my work, which is slightly more flexible, with my childcare, which is very inflexible. I’m currently three days a week in the office and two days a week with no commute. That’s not the same as having wildly different childcare schedules on different days.
We need to think through, what gets us to the point where the benefits of flexibility at work translate to flexibility at home. I get a partial benefit, and I’m grateful for it. But it’s not the same as having one day a week where my kids can be home and not go to preschool. On the days I’m working from home, I can start a sourdough in the morning, and no one at the office cares that I’m doing turns of the dough in between meetings. That’s great, but it’s not as central as what I want to do with my kids.
N: What can we do to amenitize the Third Oikos as it relates to childcare?
The biggest challenge is standing up more pluralistic, home-based childcare, which tends to be more flexible. Very flexible childcare is hard on the providers. If you want more flexible childcare, you’re going to have to subsidize it somewhere — whether by subsidizing parents, so they can afford childcare that is more flexible and thus more of a pain to offer, or subsidizing providers. Filling out a full roster among kids who are going three days a week is much harder for the provider.
Not Technological but Anthropological
N: The specific line you’ve been tweeting is, “The challenge we currently face is not technological but anthropological,” from the encyclical. Can you dive into why you love that line?
Many of our problems are anthropological, in that whenever we’re trying to reason about what is just to ask of or do to human beings — you always need to be able to answer: what is a human being? How do you know what’s just to do to them or not?
N: How should we take this into remaining human in the face of immense technological change?
Insofar as it’s about, “Who are you when your capacities don’t make you distinctive or good enough?” it’s a profoundly beautiful pro-life encyclical. A lot of arguments — on the pro-life and the pro-choice side — are made about babies and the elderly from the question of their capacity: this person cannot feed, or support themselves; cannot excel in these domains, can’t articulate their suffering, and is therefore possibly not a person. Part of what the Pope highlights is that AI will leave a lot of people who currently have their identity grounded in their doing, feeling like that sense of themselves is being stripped away. A computer is going to be better at that particular doing than you are, at least good enough that people think you’re substitutable with a computer. Some people are going to be supplanted in this way. Do they cease to be people, when their doing is not important? The Church’s answer is that their being is actually what gave them their identity and their worth — being created by God in His image, loved into being, conserved in existence. You always get to rest secure in that, whether you are an infant in the womb, an elderly person with dementia, or Garry Kasparov and you’ve just been beaten by a computer.
N: Do you take for granted that some massive amount of work is going to be replaced in the next decade by AI?
Yes. What I’m less sure of is how much it will create opportunities to do different kinds of work. People assume it will cause massive unemployment, and historically that’s not usually true. But when I hear people go through the near-term jobs they expect to replace the old-term jobs, they don’t sound like you’d hire the same people for them. No matter what, there’s going to be a very turbulent period where some folks are not getting reshuffled elsewhere in the economy.
Ask for Help With Something You Could Do Yourself
N: You said, in Plough, “To give an honest accounting of ourselves, we must begin with our weakness and fragility. We cannot structure our politics or our society to serve a totally independent, autonomous person who never has and never will exist. Our present politics can only be challenged by an illiberalism that cherishes the weak and centers its policies on their needs and dignity.” You then wrote Dignity of Dependence.
How would you recommend readers make small changes to embrace dependence?
When I give book talks, the one piece of homework I’d most like people to commit to is to ask for help with something within the next week. The challenge is asking for help with something you could do by yourself — you aren’t totally back against the wall with no choice but to ask. I think it’s good to get into the habit of asking. You’re communicating to everyone, “It’s normal to ask for help with something we both know you could handle.” It’s normal to not wait for an emergency to say, “I’m having a tough week. I don’t want to cook. Would you invite me over for dinner?”
N: I’m curious how you think about this specifically related to raising children. You say, “As Jon Askonas notes, in ‘Why Conservatism Failed,’ his essay on technology and tradition for Compact magazine, technology is most corrosive when it breaks the chain of apprenticeship to mastery. It’s easy and usually cheap to outsource entry-level work to computers or offshore workers. But, as Askonas observes, ‘these technologies knock out the bottom rungs of skilled practice that allow for the development of mastery in the first place.’” I think this also applies to individuals and children. How do you think about preserving the chain of apprenticeship to mastery in parenting?
I think about, “Where are my kids seeing people struggle and be praised for struggling?” I’ll highlight this when they see their brother doing something again and again as he’s trying to master it. He recently learned how to jump, and it’s that very small two-year-old jump where he’s getting an inch off the ground with maximum effort, and he’s thrilled. “Look at him jump.” They’ll say, “But he’s not very high.” I’m like, “He’s just learned. He’s trying to figure out how to get his body to go higher, and he’s figuring it out by doing it.”
We have art up from the kids around the house, then we’ve got some actually good art that my husband has drawn. We’ll look at it sometimes and they’ll go, “That one’s just scribbles.” I’m like, “You got to where you are by scribbling. To do what Alexi has done over there, you will have to keep making art that is less good than his.”
N: Andy Crouch said, “It’s amazing how many justifications people give for introducing all kinds of devices. I’ve got lots of them in my house, but it’s amazing how often it’s about getting more productive at being a family.” He uses this framing of devices versus instruments:
Devices give us superpower without formation — which is a little what you’re pointing to with the apprenticeship-to-mastery chain.
Instruments demand skill, and form us.
What are the instrument-type technologies in your house that actually form you and your household, versus device-type technologies you’ve perhaps kept out?
One thing I really like from Andy Crouch‘s Tech-Wise Family was him saying, you can’t just have an absence in the house. You can get rid of your TV, but you need something that is the place you turn your attention to. We have markers on our dining room table all the time, so it’s easy to pull up a chair and start drawing. There are books all over the place. We have a big gym mat, so it’s easy for the kids to pull out and be like, “Now it is time for tumbling passes.” Really thinking about what are the things that invite you to sit down and use them. As we get bigger, I want to add musical instruments. I would love to get to the point where our kids just get together and jam together.
N: One of your closing quotes is about AI-generated art and the way that amateurism is already being crowded out by advances in technology. “Long before we began streaming music, radio and records began squeezing out communal singing. While farms were full of shared work songs, offices are full of earbuds.” You specifically say, “I wanted them to practice sitting through that queasiness and finding something on the other side.”
Do you specifically push your children away from frictionless experiences?
I think about how to give them the right level of friction, particularly around social practices. When someone’s got a little bit of an attitude, when is that part of the friction we’re all living with? When is it, “You need to change your behavior”? Music instruction is one where we have a tradition of giving people the exact right amount of struggle for a sustained period of time, with a chain of mastery. When it comes to virtuous behavior with siblings, I have much less of a sense of, “Is the right amount of struggle for them to be able to learn from.”
Expect to Flame Out
N: Do you have any advice for readers of The Third Oikos?
A lot of my advice is iterate, and expect to do things that will fail, because you are trying to expand the envelope of what are normal ways to work and have a family:
Hold your plans and identity lightly.
Expect to flame out.
Expect to have problems that your friends don’t have, because you are trying to explore an underexplored region of work-life balance.
So: be ready to pull back and change. Don’t get too attached to your current iterations such that you stick with them when they turn out to be genuinely bad ideas. It’ll make you a lot freer to find good ideas.
N: Do you have a way that you’ve iterated that you had to pull back from?
I’m always trying to iterate on what the best way to share priorities within the family that genuinely work for everyone and are not, “Let’s all assign each other deliverables and then check if we’ve done them.” I still haven’t hit on the one we’d do our whole lives. Your family is always growing and changing. For many things in your life, you will never hit on a strategy that lasts more than 2–4 years. By then your family will be different and you will revise it.
N: Anything else you want to say?
It’s going to be a very exciting time to be alive, in both the negative and positive senses. The more you enter the next five years with the attitude that you’re trying to be anti-fragile and flexible, that you’re trying to encounter turbulence and build a family structure that’s going to get stronger in the middle of turbulence — the better time you’re going to have.
This interview series is made possible by the Foundation for American Innovation and the Institute for Family Studies.
Thank you to Harry Fletcher Wood for his edits.
"It's the best possible time to be alive, when almost everything you thought you knew is wrong." h/t our guy Tom Stoppard (clocked it and couldn't resist)
Great interview. I especially appreciated this closing quote: "Expect to have problems that your friends don’t have, because you are trying to explore an underexplored region of work-life balance." True!