hr:after { content: "𓃰" !important; line-height: 1.5; } In March 2025, I went on a Jhourney meditation retreat that was one of the most profound experiences of my life, and deeply reshaped how I related to myself. If you had told my pre-retreat self that this was going to happen, I wouldn’t have believed you. I’d done some meditation before—including a 10-day vipassana retreat—and while it didn’t do nothing, I was underwhelmed. I felt pretty resistant to spending that much time staring at the inside of my head: it seemed really hard to actually trust anything I learned that way, because it was such a complicated system. And besides, my brain seemed to work fine the way it was. I’d read some writing by serious meditators who seemed to be having a different experience, filled with insights and bliss, but it wasn’t one that I felt particularly drawn to. That much navel-gazing and wireheading felt self-indulgent, and anyway they seemed weird enough that whatever they were doing probably wouldn’t work for me. Then, in a moment of life imitating Bay Area House Party, we got Jhourney, a meditation retreat startup promising to speedrun you to the bliss part (tagline at the time: “Life-changing meditative bliss used to take thousands of hours to learn. We teach it in a week.”) When I heard them strongly recommended not only by the serious meditators I’d been reading, but also by a couple more hard-nosed coworkers, I decided to see what the hype was about. Jhourney teaches a style of meditation nominally focused on altered states called jhanas. Jhanas are blissful-feeling states that you can “relax into” if you release enough of what you might call tension or clenching or tanha, and then focus on an enjoyable open-hearted sensation like smiling, a joyful memory, or feeling care for a loved one. If done right, you can start a feedback loop of enjoying the enjoyment, and end up in a state of deeply absorbed euphoria. I say Jhourney is nominally focused on that because the jhanas are actually kind of a Trojan horse for improving your life and relationships, which somehow doesn’t sell as well as wireheading. Jhourney’s unofficial motto is “come for the bliss, stay for the personal growth.” The growth happens because a lot of the tension you’re trying to release in jhana meditation is downstream of repressed or “stuck” feelings, either small ones (“I don’t want to be hearing that sound over there” leading to micro-clenching the head and neck) or big ones (“I can’t let myself feel this sadness or I’ll cry and that would be shameful” leading to tensing the various face and chest muscles that would otherwise be helping you cry). In order to get into jhana states, a lot of people (like me!) end up having to work on untangling knots of emotional clenching, and this usually leads to a lot of growth. My first experience of my Jhourney retreat was showing up and being handed an 80-page handbook of meditation instructions. This already blew my mind a little, because I had never read anything about spirituality or emotions that I considered good. The “best” stuff I’d read about the mind was vapid pop-psychology, padding out truisms with engaging fluff until the result somehow became a marketable book. The rest was indistinguishable from astrology—it was never clear enough that I could tell whether it applied to me, which meant it didn’t seem to make falsifiable predictions. As for spiritual writing, it mostly felt like word-association mumbo-jumbo, with authors throwing around words that had the right vibes but that I wasn’t sure they themselves even really understood. Heck, the previous meditation retreat I’d been on had included watching an hour-long recording of the now-dead founder talking about how he could sense quantum vibrations. The Jhourney handbook didn’t have these problems, because it was written by software engineers. It was epistemically conservative and shockingly lucid, completely mumbo- and jumbo-free. To help with the inherently fuzzy language, they explained everything from multiple angles. They gave clear gears-level explanations of why they thought things worked the way they did. They even took a detour to explain their teaching philosophy so that students were oriented about why they were doing what they were doing. It was masterful pedagogy. Between the written instructions and the teachings from live meditation sessions, pretty soon I could get to a point that felt like the “on-ramp” to a jhana. But every time I got there, I would get stressed and “grabby” about what to do next, and “fall off” the ramp. By the time I got to day 4 of the retreat, I was feeling really frustrated about this, in a way that was starting to loop on itself. I was frustrated that I couldn’t reach jhana, and frustrated that the frustration was making things harder. I tried Jhourney’s recommended way of working with negative emotions, which was a self-compassion meditation. But no matter how much I tried, it didn’t really resonate; I couldn’t cultivate any emotional experience of self-compassion. In fact, I realized I couldn’t remember ever having had a real emotional experience of receiving compassion, and that that was probably kind of fucked up. A bunch of my friends were on the same retreat. Since I had no access to self-compassion, of course I used this realization to start worrying that they would judge me for having a hard time meditating because I was fucked up, adding even more layers to the feedback loop of doom. Days 4–6 were pretty bad. Every day Jhourney gave us a survey of “how was your day on a scale of 1-10 with 5 as a normal day?” I rated day 6 a 1.5. (To their credit, Jhourney knew this meant I needed extra help and offered lots of 1:1 time with different facilitators, although none of it made that much difference.) At this point, in one of my desperate attempts to think myself out of my feelings pickle, I started thinking a lot about the metaphor of the elephant and the rider. The idea is that people usually identify with everything that happens in their mind, but this is actually a confusion; it’s more accurate to think of “you,” the conscious part, as a small human rider perched atop a large lumbering elephant that often does its own thing. The only things that are actually in the rider’s action space are things like “say words to the elephant,” “visualize mental images to the elephant,” “direct attention to a particular aspect of experience,” etc. Everything else—including all emotions and many thoughts—is the elephant’s job. In this frame, the fact that the self-compassion meditation wasn’t working for me wasn’t really “my” fault. Whether the emotional experience of self-compassion happened was up to the elephant, and the only thing “I” (the rider) could do was to keep gently saying the words or doing the technique or whatever, and wait for the elephant to steer, at its own pace. Around that point I decided to give up on the Jhourney curriculum and just do whatever seemed like it would feel nice.1 I broke the rule of silence to ask for some reassurance from a close friend who was also on the retreat. When I got back to meditating, I made up a technique for myself where I imagined sending love and compassion to the elephant instead of to “myself.” This turned out to be a cheat code: I immediately felt an outpouring of warmth, and the reassuring things I was telling myself started to emotionally resonate. I really wish I could describe better what happened after that, but unfortunately it was a while ago and involved a lot of subtle mental movements, plus it’s hard to track what’s happening while a chunk of your psyche is liquefying. I remember a sort of sense of “going inside” the feeling of compassion and love for the elephant, having it take up more and more of my attention, and feel more and more deep, rich and meaningful. Then some kind of rush of energy and a full-body frisson that I’ve learned often happens when my brain has rearranged itself.2 When I got up and walked outside, I gradually noticed that the world felt pretty different. I realized that I’d always carried a “refrigerator hum” of subtle body tension that was now gone. Walking around the retreat center looking at the views felt amazing, like I could have spent days just melting into the landscape. The Lipton peppermint tea at the hot drink station tasted unreasonably good. I would sometimes tear up with joy or gratitude for no reason. I felt much deeper care and connection with my friends. Maybe that makes it sound a little gooey and impersonal, like I took a drug that replaced my normal self with a puddle of love or something. The actual experience was the opposite; somehow it felt like this was all happening because it was easier to be myself. The care and connection wasn’t coming from some foreign love puddle; it came out because a bunch of psychic gunk had sloughed off and made it easier for the real essence of Ben-ness to shine through. And then I used my newfound mastery of emotions and self-compassion to live happily ever after flailed around trying to integrate everything back into normal life. One of the big changes I noticed after the retreat was that my emotions got 2–3× more intense. I think this was net positive in the end, but it made coming back to work hard—I had a stressful role managing a large team, and I also needed to catch up from a week of being incommunicado, which was extra stressful. And it wasn’t exactly helpful that suddenly, if someone was annoying on Slack, it would sometimes make me want to shoot flames out my ears. Over the next couple weeks, the intensity settled back down and the changes in my moment-to-moment experience went maybe 80% of the way back to normal (e.g., I stopped spontaneously tearing up in normal circumstances). Some of them stayed, though: A lot of my shame/cringe reflex turned into a self-compassion reflex. I used to get super embarrassed by minor mistakes (things like, I don’t know, forgetting to lock a public bathroom door and having someone walk in). Now those things come with a very clear sense of “gosh, what a normal-person type of mistake that millions of other people have also made, it probably didn’t even register for the other person.” I became much more easily moved by art. I went from being moved to tears by a poem or piece of music maybe once a year to once a week. I stayed much more aware of my more subtle emotional responses. I remember listening to some instrumental folk music I’d probably listened to 100 times before, suddenly noticing that the melody felt deeply nostalgic and then realizing that was two levels further out on the feelings wheel than I’d ever felt for music. I still felt much less of a need to be distracted or stimulated than before. I used to listen to podcasts at 2× speed whenever I wasn’t fully focused on a task (e.g. if I was doing chores or walking). Now I have no desire to do this, and when I do listen to podcasts, 2× speed feels unpleasant. Similarly, I started to dislike a lot of restaurant food, and to really enjoy very simple home-cooked meals that I would have considered too bland before. Friends continued to mention that my body language was different. One noted: “more upright posture, more open shoulders, more fluid and gentle.” Another described me as “‘leaving less,’ as in, spending less time ‘out of the room’ in interactions.” These were great changes, but even better, a bunch of mindset and relational shifts also stuck around. Mindset-wise, I guess I’d just say I got feelings-pilled. If you’d asked me what the deal with emotions was before the retreat, I probably would have said something like: Positive emotions are nice, although you shouldn’t let them distract you too much from your long-term goals. Painful emotions are responses to stimuli that are part of our evolutionary inheritance, but are largely maladaptive today because we’re in an environment so different from where they arose. Assuming you have good enough self-control not to act out on them, their main effect is to make you dumber, which you should mitigate by not engaging with whatever makes you emotional until you’ve chilled out. My new view is more like the following (this is still an oversimplified strawman and reality is a lot messier): All emotions are important and beautiful components of unconscious/intuitive cognition.3 However, they sometimes create impulses to do things that aren’t actually good ideas. In the process of socializing ourselves not to follow those impulses, we’ve been trained to try to make the emotions themselves go away in painful ways, by repressing them or clenching up around them. Unintuitively, repression and clenching actually cause the emotions to “stick around” in some sort of partially metabolized state, which has negative side-effects, like anxiety, thought-looping, numbness, blind spots, impaired reasoning, bringing up secondary emotions as defenses, etc. A different way of working with these emotions, that’s better for you in the long term, is to figure out how to welcome and accept them. This eventually leads to them feeling less bad, and giving you more impulses that are good ideas and fewer bad ones. But it’s not as simple as “just stop repressing.” Welcoming emotions requires fully feeling them; if they’re strong, that can be too overwhelming to work unless you have a deep felt sense of safety. That safety can be provided in many different ways, e.g. a therapist, friends, some kinds of meditation, etc. If you don’t have access to enough safety, repressing or clenching temporarily might be your best option. The main thing that changed my view here was spending days at the retreat paying close attention to my own emotional experience. For example, near the beginning of the retreat, one of the facilitators claimed that thought-looping was usually a sign of a stuck or repressed emotion. I was really skeptical, but then I had several very clear experiences of thought-looping around something, going off to a private place to cry about it, and immediately stopping the thought spiral and relating to it differently.4 Similarly, I’d ended a long-term relationship right before the retreat, which I’d felt a lot of internal conflict and self-doubt about. My therapist had often told me things like “if you felt enough of your feelings you’d feel clear about this decision,” which sounded crazy to me at the time (uh, it’s a really hard call and there are a lot of tradeoffs that I don’t know how to weigh!). But on the last day of the retreat I noticed that I felt much clearer that a lot of the things I didn’t like about that relationship were real and important, and felt much more confident in my choice to end it. Of course, I’d already heard plenty of people say things like “you can’t make this kind of decision logically, you have to listen to your heart,” but I never really understood what they were talking about. In retrospect, I just didn’t have the ability to do the “listen to your heart” internal move, because the pipes were clogged by too much repressed gunk. I wish those soundbites had included a second sentence like “of course listening to your heart can be much easier said than done, so if it feels hard or unclear for you, here are some first steps to get started with, and be prepared for it to take you many hours (or years) to figure out what your heart is trying to say.” This new mindset really shifted the way I related to my emotions. While I still often experience them as painful, it’s much less than I used to, and now I start from the assumption that they’re not “actually” painful or bad, and that the best thing to do with them is to figure out how to accept them, welcome them, and find the wisdom or beauty in them. Overall this feels a lot better—when I run into something stressful or hard, instead of just flailing around not knowing what to do about it, it feels more like I have some kind of sense of direction or overall orientation, which is really comforting and grounding. I also noticed that a lot of these ways of thinking about emotional difficulty within myself were also useful metaphors for thinking about emotional dynamics between people. Just like resisting your own emotions is a common coping strategy but ultimately doesn’t work very well, resisting other people’s emotions is also a really common but damaging pattern, which I would guess is very involved in a lot of (most?) relational damage. For example, I realized that a big part of the root problem of the relationship that I had just ended was that both of us were missing the capacity to accept a bunch of each other’s emotions, which was something I hadn’t been able to articulate clearly at the time. I now think practices explicitly focused on welcoming each other’s emotions are a really valuable tool for nurturing relationships over time. In fact, I started to notice that a lot of sticky problems—both in my personal life, but also the type that I ran into as a manager—were partly downstream of people resisting emotions of one type or another. Alice is hard to communicate with, because she frequently monologues about unimportant details, because she wants to prove she understands everything, because she has a bunch of stuck fear/resentment about not being taken seriously. Bob and Clara have a persistent disagreement about strategy, because Clara doesn’t care enough about Bob’s opinion to engage, because Bob was cruel to her once; Clara never complained because she’s avoiding the feeling of having been hurt by it. Dave’s team is underperforming but Erin, the exec sponsor, doesn’t want to manage him out, because she’s scared of the conflict and of making Dave’s reports, who like him, angry. Of course, just because a problem is caused by stuck emotions doesn’t mean that unsticking them is the best way to solve it; but it was still a really useful lens to view what was going on. The other shift that stuck around was in my relationships. I made a huge improvement in my friendships, which a few different things contributed to: I felt a lot clearer about what I wanted from close friendships—mainly, a strong felt sense of safety and care—and that this felt like a big missing piece in my life. I also started getting better at feeling those. With a lot of my shame reflex dissolved, I felt generally safer with people overall—my intuitive predictions about how they’d respond to things I did felt more positive. I also got a lot better at noticing and appreciating the different ways people expressed care for me. Because I felt generally safer, I also got more willing to take risks or be vulnerable, which helped build closeness faster. A friend reflected that I seemed more courageous. This also meant that my “friend type” changed—I cared more about emotional connection and less about intellectual connection. Luckily, even though I live in a really heady milieu, I was still able to find a lot of big-hearted people and gradually build up a set of close friends who are wonderful at both. So far, this is the change I’m the happiest about. My dating life changed a bunch as well: I started being able to feel much more strongly attracted to people. For example, later that year, I got a crush on someone that was stronger than any crush I’d had in high school. I had a run of anxious-attachment-ish experiences, which I’d never had before, although they got way milder over time.5 The extra safety and courage I mentioned above were helpful in dating too: I got much more comfortable with communicating tricky things or being in weird situations (e.g. ones outside the standard script of “meet someone on an app, go on some dates, become exclusive”). A friend commented that it seemed like I had more degrees of freedom. These changes have been really wonderful overall, but also kind of intense. Becoming much more emotionally aware solved a bunch of my problems, like wanting deeper friendships or not understanding why my relationship was unsatisfying. But it turns out winning that boss fight just made all the enemies level up. My old problems got replaced with horrible new problems, like that sometimes my newly deep friends and I would have conflicts, or that I would be more into the person I was dating than they were into me. The part of my life where I feel the most mixed about the impact is work. About six months after my retreat, I got a pretty bad case of burnout and left my role managing a big team for a significantly less ambitious IC role. I don’t think the retreat was the main cause of my burnout—the main cause was that I didn’t have enough background in the area I was managing to have the type of impact that I wanted to, with a side helping of some difficult working relationships. But it turns out my new psyche had also gotten worse at repressing or avoiding emotion, and that made everything harder. I think of repression as the emotional equivalent of technical debt or deferred maintenance: a way of avoiding an immediate cost, in this case feeling uncomfortable feelings, in exchange for paying a higher cost later to clean it up.6 My role exposed me to a constant stream of low-grade painful things, like people being disappointed or annoyed at me, me being disappointed or annoyed at other people, projects not going well, office snacks being replaced with worse snacks, and so on. With less ability to avoid or repress, I had to feel more of them fully as they came up, and that was really draining. It also required enough time and attention that I had to defer a bunch of maintenance on my personal life. Even now that I feel like my energy levels have mostly recovered, I’m still not sure whether I want to go back to the center of the vortex. It’s not just that I would have to start deferring maintenance again; I’m also much more aware of a lot of maintenance I’d already deferred and really want to clean up—things like investing in friendships, like I mentioned above. If I were only working toward my personal growth and happiness, I’d say this change was clearly good. My life feels much richer and more whole, and taking a less ambitious role forced me to release some layers of ego attachment to having a “shiny” job or career, which was deeply freeing. But… I also care a lot about my impact on the world, and I think the next few years will probably be a critical period where my work could be especially high-leverage. From that perspective, it’s sad to feel resistant to maxing out on work right now. I feel pretty unsure about what to take away from all this. Here are some disconnected reflections. I would never have said that I had a problem with self-compassion or self-esteem before doing this retreat, because I was able to say the right self-compassionate words when I directly asked myself things. But from my point of view afterwards, it’s clear that I did have a big self-compassion problem; even though I could say the words, I wasn’t really feeling them or acting like they were true. Having the actual embodied experience and habits of self-compassion is the closest I’ve come in real life to The Vitamin.7 Jhourney is doing something really cool and is way better than most/all other meditation retreats on several axes (amount of support available, pedagogical excellence). That said, you probably shouldn’t expect to have this life-changing of an experience; I would guess I had something like a 95th-percentile-plus outcome in terms of long-term effects. I still think it’s awesome as an introduction to both meditation and embodied emotional awareness. I feel like I got really lucky on timing: if the retreat had ended one day earlier, I don’t think I would have gotten to the life-changing part. That freaks me out a lot. At first I concluded from this that I should get super into meditation. Then I did two more retreats (another Jhourney retreat and a Dustin DiPerna introduction to mahamudra retreat) and neither one of them had nearly as large of an effect. The second Jhourney retreat was really helpful in reinforcing my daily practice, and I do think a daily meditation practice was helpful in stabilizing the changes that became permanent, but I’m not even totally sure about that. Jhanas are definitely real. Also, it was kind of wild hearing somebody tell me something that sounded totally fake (“achieve bliss on demand using nothing but your brain”) and then back it up with an 80-page engineering manual and meticulous data on success rates. Overall this made me much more likely to believe that various other types of “woo” phenomena are real, at least in the sense that people are accurately describing their experiences. (I still believe the universe runs on physics, but a lot of woo things have physics-compatible explanations, especially if you buy that people’s intuitions can sometimes do spooky things.) I described this as “chang[ing] my personality” in the title, but I don’t want to oversell the magnitude. I do have a lot of conversations where someone asks me “so how come you’re so <like X>” and I tell them “I did this weird meditation retreat a couple years ago.” But also, there are a lot of different aspects of personality, and even though a bunch of those completely changed for me, most of them are still the same, so I’m still very similar to my past self in an absolute sense. What flags should tip you off that you should maybe be staring into your emotions more? Here are some things that I think might be clues (a lot of which described me, in retrospect): You often get stressed and stuck in thought loops You’re easily annoyed or frustrated You have too much scarcity mindset—you often worry this is the best job or relationship or whatever that you’ll ever have, in a way that’s not justified by the fundamentals You seek out a lot of distraction or stimulation; it’s not very enjoyable to just exist in the present You feel a lot of internal conflict or uncertainty about what you want There are parts of yourself that you really don’t like or wish were different You feel some missing depth, richness, or meaning in your life but can’t put your finger exactly on what I’m also just left with a lot of questions: Was this set of experiences… good? I’m really confident that it will be good for my own long-term life happiness. But the timing meant that I feel less willing to sign up for intense work during what might be one of the most critical periods for humanity, which feels bad even if the change was positive. I feel kind of unsure how to balance these. My shoulder Jeremy Bentham says I should have just kept playing push-pin. My shoulder, uh… deva? says if I follow my heart my impact on the world will be higher, even if it’s less predictable or legible. I don’t really feel like I buy either of these. It seemed like before this I was in a personality attractor basin with a lot of numbing and repression. How exactly did this happen, and more importantly, how can I/we avoid having it happen to as many people in the future? I have some sort of fuzzy leads on this (e.g. when I was young it was really easy to make me cry so I got picked on a lot in school), but not a particularly complete picture (e.g.: does this happen to everyone who has that experience? If not, what makes the difference?) Mechanistically, what did the elephant meditation do? Why did it work so suddenly and create such a lasting shift? (Was that in fact what was responsible for most of the lasting shift? How much of it was instead about what I learned at a cognitive level?) Is the glowy, “easier to be the essence of Ben” state that I ended up in right afterwards something that can be stabilized (or have aspects stabilized)? If so, how? More generally—where do I go from here? I’m convinced that doing the right type of introspection or meditation type thing for a week can unlock amazing things, and it feels like there are more amazing things out there to unlock, but I wish I had a better way of navigating towards them than semi-randomly trying things. A draft reader asked what I would tell my past self, or someone like me, about this arc. Ultimately, I’d boil it down to: There are probably a bunch of feelings that you’re refusing to welcome into your experience, and this is probably involved in a bunch of the things that are unsatisfying about your life and relationships. You can improve this by gradually, in a safe context, paying loving attention to the uncomfortable parts, from a place of wanting to know and care for yourself rather than to fix yourself. When that’s hard, remember that it’s not your fault. You’re just the rider; elephants gonna elephant. Let it go where it needs to and keep loving it as best you can. Thanks to Alex Allain, Catherine Olsson, Elena Lake, Jess Ocean, Rahul Dalal, and Sasha Chapin for feedback on a draft of this post. Ironically, Jhourney more or less recommends doing this in various parts of the handbook, but I was too into following rules to follow the part of the rules where they told me to stop following the rules. I don’t think this strictly qualifies as a jhana by Jhourney’s rubric, because it wasn’t stable and self-sustaining, but it otherwise felt close to how they describe first jhana. I do mean all, even ones that our culture really doesn’t like—for example, anger is a sign that something you care about is threatened and needs protecting, and fully welcoming it can help bring clarity about what exactly needs protecting and how. If you’re curious to learn more about the beautiful and constructive aspects of negative emotions, I recommend the book The Language of Emotions, Joe Hudson’s podcast (search for the emotion you’re interested in), or here are some specific articles summarizing his views on anger, fear, and shame. It was a lot easier to see this clearly on the retreat than in normal life: doing lots of meditation both made it easier to notice my own thought processes, and also faster to “unstick” or welcome the underlying emotions. I’m not totally sure what was up with this; I think it partly had to do with calibrating to the new level of attraction I could feel. Like tech debt or deferred maintenance, sometimes repression or avoidance can be the right strategy, if you’ll have more resources to deal with the problem later! “My deepest darkest fantasy is that I collapse on the street and I am rushed to the hospital. They perform a bunch of tests and find out I am severely deficient in some kind of vitamin. Then I start taking the vitamin and I become the happiest cleverest person alive because all my problems were caused by this one deficiency.”

A popular icebreaker in San Francisco these days is “How would you spend your life if AGI meant nobody needed to work?” For me, I think a surprisingly big part of the answer is a dorky-sounding kind of folk dance called contra dancing. I started trying to answer that question by thinking: what are the things I do atelically—because I enjoy them for their own sake, not in pursuit of some longer-term goal? For me, a lot of that has to do with things that are (1) physically joyful, and (2) help me feel connected to other people. My pitch for contra dancing is that among physically joyful and connecting activities, it’s one of the ones where it’s easiest to get to the point where it’s fun, and therefore one of the best to start out with. Many other forms of dance require weeks of lessons before you’re even encouraged to do it socially at all. By contrast, the format of contra dancing means that you can go to a half-hour beginner lesson before your first dance, and there’s a good chance you will be having a lot of fun by the end of the evening. What’s more, the fact that it’s so easy to start having fun shapes its community and priorities, such that it has among the best vibes of any activity I do. I first encountered contra in middle school. My mom ran an intentional community, and we had a housemate move in named Bree. Bree was obsessed with this thing called “contra dancing,” and every week she would try to convince me and our other housemates to come with her. Which I absolutely refused. I was an extremely uncool middle schooler, and that meant I was terrified of doing anything that even whiffed of uncoolness, lest I give my classmates another reason to judge me. I was also deeply awkward; I’d never even been to a school dance and barely talked to girls. But Bree was persistent, and one of our other housemates got hooked, and eventually I was intrigued. By then, though, I was dug in as a contra hater, and I was scared that if I admitted I had changed my mind, my housemates would make fun of me. So I kept refusing. Finally, my housemate Thomas, who was even more of a skeptic than I was, told Bree that he would only go if I went, presumably so that she would stop bugging him and bug me instead. Aha—my golden opportunity! I could pass off my change of heart as a prank on Thomas. “Okay, sure! It’s a deal!” Bree and I showed up at the Concord Scout House one Thursday evening and jumped into the next dance. It was an unusually complex square dance, and I got confused—in fact, so confused that my entire square ended up giving up halfway through.1 I was mortified. Not only was I doing a deeply uncool activity, I was the least cool person there, ruining it for all the slightly less uncool people with my incompetence and lameness. Except that the other dancers didn’t seem to see it that way. Instead of resenting me or making fun of me, they said things like “Gosh, that one was really tricky!” and “Sorry, that’s really not what it’s usually like!” and “Please don’t give up, try a few more dances! Want to dance with me?” I tried some more dances, I didn’t cause any more collapses, and by the end of the night I was overflowing with exhilaration and joy. I went back the next week, and the week after that. I went to the twelve-hour Snow Ball and then the weekend-long Flurry Festival. I got to feel cool for the first time in my life when people started being excited to dance with me, and even cooler when some of them asked me on dates. It was a huge part of my life for a while, and although I’m now dancing at maybe a quarter of my peak intensity, it’s still one of my most joyful and treasured things I do. This happens to about one in ten people I take contra dancing: something clicks and it becomes a big part of their life. So what exactly is contra dancing? When people ask me this I often feel stuck, because describing the mechanics of a contra dance doesn’t really capture its essence or why it’s fun, but without understanding the mechanics, the essence doesn’t really make sense. So I’ll try both. But you have to promise to read through to the essence part, and not just bounce off if the mechanics sound silly. Mechanically: you show up to the dance hall. You ask someone to dance, or they ask you. You join a long line (“set”) of other couples and take hands in a four-person group with one adjacent (“neighbor”) couple. A caller stands at the top of the dance hall and does a “walk-through” of the dance you’re about to do, calling out a series of figures (“circle left three places,” “do-si-do your neighbor,” etc.) At the end, you’ve moved up or down the line, and you’re ready to do the same thing with some new neighbors coming at you. Next to the caller is a live band. (They probably sound a bit like this.) The pianist plays four potatoes and the fiddler launches into a reel. The caller calls out the figures for the first few times through the dance, then drops out as the dancers get into flow. It looks a bit like this video, although I don’t know how much this will transmit the vibe, since contra is a lot more fun to do than it is to watch: Bonus: you can see high school me in this dance! I'm in the dark red T-shirt at the very right of the frame at the beginning. To me, the essence of contra dancing is about flow, joy, and community. You can’t really tell from watching, but a lot of what makes for good contra dancing is learning how to trade momentum back and forth (“share weight”) with other dancers so that each figure flows seamlessly into the next one. When you get this right, it feels amazing. Subtle changes in how your partner holds your hand cue you into the next figure. The dance becomes effortless. You can turn your brain off and just do what the giant dancing super-organism invites you to do. It’s also physically joyful. The core figure of contra dancing is called the swing, in which you and your partner take a waltz-like hold and pivot around a shared center. Done right, it feels like a cross between flying and a world-class hug. Even outside of the swing, the shared weight, smooth momentum, and twirling “flourishes” will make you feel weightless, graceful and deeply connected to the music and the other dancers. Lots of kinds of dance feel flowy and exhilarating when done well. What makes contra different is how easy it is to get there. Most forms of dance require weeks of lessons before they get fun. In contra, all you need to do is show up for one beginner lesson half an hour before the dance starts.2 Of course, there’s plenty to learn after that—improving your swing technique, learning how to share weight, and where to put flourishes for the best joy and flow—but all of that is for getting you from a 8/10 to an 11/10 on the fun scale; getting to an 8 is pretty straightforward. So contra makes it easy to have a baseline level of fun dancing with anyone. And because it’s a group dance, you end up feeling connected to your entire set, not just your partner. I think those two things are behind my other favorite part of contra dancing, which is how friendly and welcoming the community is. Many kinds of dance are a bit snooty—the experienced dancers look down on newbies and try to avoid dancing with them. By contrast, my experience at my first dance, where I caused my square to crash and burn and was met with apologies and “I hope you’ll give it another shot,” is typical for contra. A lot of contras explicitly ask experienced dancers to dance with newcomers. It’s just hard to be snooty when you’re having so much fun! You want to share it with everyone.3 As draft reader Chloe put it: “I think in many ways, your story of your first dance is the heart of it—you can’t do it wrong. Or even if you do, it somehow leads to more love.” In my opinion, this makes contra dancing one of the best entry points to dance: Each dance is walked through, so you don’t have to worry about deciding what to do. You can get to an 8/10 fun level, where practice becomes rewarding instead of a chore, really quickly. The community is incredibly welcoming, which makes it a lot less stressful to be a beginner. While it’s structured enough to be beginner-friendly, there’s also enough room for improvisation and technique to give it a lot of depth. This makes it a great on-ramp to other dances and movement practices. When I started contra dancing I had a lot of fear and blocks about improvised dancing (for example, I didn’t feel comfortable dancing at standard American high school/wedding style dances), but recently I tried out fusion and contact improv and had fun at both. It’s pretty common for people to use contra as a gateway into more difficult forms of dance. Most importantly, though, it’s just incredibly joyful on its own! It’s the only activity I know of where I’ve had multiple friends mention that every time they go, their cheeks hurt from smiling so much. Beyond just fun, multiple draft readers independently commented that contra dance is a precise opposite of many things that bother them about… the rest of life: Much of my life happens on a screen in motionless silence; contra is as three-dimensional, movement- and sound-filled as you can get. The default mood of a lot of spaces is a sort of ironic detachment.4 The default mood of contra dancing is earnest joy. In everyday life it’s easy to end up atomized and isolated. At a contra, everyone does the same steps and makes the dance together; it’s deeply communal. In a lot of social contexts (especially in San Francisco), I often feel like I’m being “sized up” for how interesting or important I am. At most contras, people are just happy I’m there. Many things I do (work, choral music, blogging…) reward excellence above almost everything. Contra welcomes imperfection: we’d rather have an amateur live band than recorded professionals, and don’t believe in more than half an hour of organized teaching. This makes it a grounding and nourishing antitode to a lot of everyday stressors. When I was so drawn to it in middle school, I don’t think it was just about the fun: on some deep level it was very good for me. If I’ve gotten you excited enough to try contra, here’s what you should do: Go to try contra dot com to find dances near you. If there are multiple dances, I recommend trying to figure out which one is the largest (larger dances tend to have more energy and better vibes), although that might be tricky to figure out from the websites. Make a note of where and when the dance is, including the beginner lesson. Remember to show up beforehand for that! Dress code wise: contra dancing is generally light cardio; wear something you are happy to be active in.5 Most people dress pretty casually; many women (and some men!) wear skirts, especially skirts that do fun things when you twirl. Look at the dance site to see if they say anything about footwear; some dances request that you wear soft-soled shoes with clean soles to avoid damaging floors. Bring a water bottle! There are fountains at most dances but it helps to be able to hydrate more quickly since the breaks between dances are short. If you go to a dance and like it, the easiest way to go from 8/10 fun to 9.5/10 is to find someone with a really good swing and ask them how you can improve your technique. (If you’re not sure, look for someone who’s fast and smooth.) They will be tickled that you asked!6 If you have a friend who contra dances, try going with them! They will be thrilled to bring you and it’ll be even more fun for both of you.7 Have fun! I hope you smile so much your cheeks hurt. Thanks to Jeff Kaufman, Alex Allain, Chloe Lubinski, and Jessie Brown for commenting on a draft of this post. Further reading/listening/other consumption: My playlist of favorite contra dance music (because every dance has live music, contra has a thriving music scene that punches way above its weight!) Jeff Kaufman, Contra Dance as a Model For Post-AI Culture try contra dot com This is at least a 1-in-10,000 event; I’ve never seen it happen again in over 20 years of regular dancing. In fact, you can probably get away without even that! Another benefit of this is that contra is much more intergenerational than most forms of dance. I have dance friends in their twenties and seventies! At least for me, when I overuse ironic detachment it has subtle but far-reaching effects on how I see and engage with the world. It’s an easy way to amuse people, but ends up masking or numbing out a lot of more “real” responses. I’ve found it really interesting and a bit psychoactive to play what I call “the ironic detachment game,” in which I am banned from responding to anything in an ironically detached way. I personally sweat a lot and usually bring multiple shirts to change into, although most other dancers I know don’t need to do this. Teaching a swing is a separate skill from just having a good swing, so you may want to ask a few different people. I recently started a mission to get my friends into contra dancing (hence also this post)! It’s going great and it’s made it way more fun for me!

My few most productive individual weeks at Anthropic have all been “crisis project management:” coordinating major, time-sensitive implementation or debugging efforts. In a company like Anthropic, excellent project management is an extremely high-leverage skill, and not just during crises: our work has tons of moving parts with complex, non-obvious interdependencies and hard schedule constraints, which means organizing them is a huge job, and can save weeks of delays if done right. Although a lot of the examples here come from crisis projects, most of the principles here are also the way I try to run any project, just more-so. I think excellent project management is also rarer than it needs to be. During the crisis projects I didn’t feel like I was doing anything particularly impressive; mostly it felt like I was putting in a lot of work but doing things that felt relatively straightforward. On the other hand, I often see other people miss chances to do those things, maybe for lack of having seen a good playbook. So here’s an attempt to describe my playbook for when I’m being intense about project management. (I’ve described what I did as “coordinating” above, but that’s underselling it a bit; it mattered a lot for this playbook that I had enough technical context, and organizational trust, to autonomously make most prioritization decisions about the project. Sometimes we instead try to have the trusted decisionmakers not be highly involved in managing execution, and instead farm that out to a lower-context or less-trusted project manager to save the trusted decisionmaker time, but IMO this is usually a false economy for projects where it’s critical that they be executed well.) Focus For each of the crisis management projects I completely cleared my schedule to focus on them, and ended up spending 6+ hours a day organizing them. This is a bit unintuitive because I’m used to thinking of information processing as basically a free action. After all, you’re “just” moving info from place to place, not doing real work like coding, right? But if you add it all up—running meetings, pinging for updates, digesting Slack threads, pinging for updates again, thinking about what’s next, pinging for updates a third time, etc.—it’s surprisingly time-intensive. Even more importantly than freeing up time, clearing my schedule made sure the project was the top idea in my mind. If I don’t do that, it’s easy for me to let projects “go on autopilot,” where I keep them running but don’t proactively make time to think through things like whether we should change goals, add or drop priorities, or do other “non-obvious” things. For non-crisis projects, it’s often not tenable (or the right prioritization) to spend 6+ hours a day project-managing; but it’s still the case that you can improve execution a lot if you focus and make them a top priority, e.g. by carving out dedicated time every day to check statuses, contemplate priorities, broadcast updates, and so on. Maintain a detailed plan for victory A specific tool that I’ve found critical for staying oriented and updating quickly is a detailed plan for victory, i.e., a list of steps, as concrete as possible, that end with the goal being achieved. The plan is important because whether or not we’re achieving the plan is the best way to figure out how well or badly things are going. Knowing how well or badly things are going is important because it tells me when to start asking for more support, cutting scope, escalating problems, and otherwise sounding more alarms. One of the most common megaproject failure modes is to not freak out soon enough, and having a concrete plan is the best antidote. As a both positive and negative example of this, during a recent sprint to release a new implementation of a model, we took a detailed accounting of all the work we thought we had to do to launch. On the plus side, this made it clear three months before launch that things were going to be very tight, and this enabled us to ask for help from another team, who loaned us someone who sped up the project a fair amount. On the minus side, we also massively underestimated a few components of the project, and because of this, we still ended up very crunched at the end. As the above example shows, having a plan can’t completely save you if you underestimate how long all the steps in the plan will take. But it certainly helps! My sense is that the main things that would have helped even more in the above case were: We were inexperienced at estimating tasks, especially tasks related to new model implementations (which most people on the team were too new to have done before), and we were too cowardly to add the requisite amount of “slop” to our plan. We didn’t check in frequently enough against the plan once we made it, or sound the alarm early enough when we went off-plan. Run a fast OODA loop OODA stands for “observe, orient, decide, act”—in other words, the process by which you update your plans and behavior based on new information. Most of the large projects I’ve worked on have been characterized by incomplete information: Our cluster’s networking is bad, but we don’t understand why. We have a correctness bug but we don’t know where it is. We need to rewrite the system but we’re not totally sure what the rewrite should look like. In fact, I’d make a stronger claim: usually getting complete information was the hard part of the project, and took up a substantial fraction of the overall critical-path timeline. For example, let’s take a recent project to kick off a training run. The critical path probably looked something like: Chips for the training run are delivered We run some tests We discover one aspect of performance is unexpectedly poor We escalate the problem with our compute partner Compute partner staffs a large debugging effort We realize we had given our compute partner an outdated benchmark that is causing them to target the wrong improvements Compute partner switches benchmark and prioritizes different improvements We share our benchmarks with compute partner so they can run the exact same code as us Compute partner rolls out improvements We test the improvements Performance is still poor and we tell them that Repeat steps 8-10 until eventually it’s good enough Practically all of these steps are about information-processing, not writing code! Even the step where the compute partner debugged the problems on their side was itself constrained by information processing speed, since there were tens of people working on the debugging effort and coordinating / sharing info between them was difficult. Overall, the project timeline was strongly constrained by how quickly information could round-trip from our compute partner’s large-scale debugging effort, through their tech lead, me, and Anthropic’s large-scale debugging effort. This pattern generalizes to most projects I’ve been a part of, and as a result, one of my most productive project management habits is to try to run the fastest OODA loop that I can. A few specific things that I’ve found help: Spend time on it: running OODA loops takes time, and is one of the primary reasons that, as mentioned above, I usually spend 6+ hours a day on running a megaproject if it’s in crisis mode. Communicate uncomfortably much: For the training run debugging, to reduce the round-trip time between orgs as much as possible, I had multiple daily calls with my counterpart at our compute partner (9am and 6pm). For the model implementation effort, I was basically constantly bouncing between different groups of debuggers, asking for updates and processing them. Track and prioritize the biggest open questions: For most big projects I’ve maintained a living doc with a ranked list of all my biggest open questions about the project. Resolving or de-risking these uncertainties basically turns into the project’s priority list. Step back and reorient frequently: Other than asking for updates, the main thing I spend time on was reorienting—looking at our list of priorities, asking myself whether they should still be the top priorities, then looking at what people were working on, and making sure those things were attacking the top priorities. I probably reviewed the project’s priorities multiple times a day as well, although I often didn’t make changes as a result. (Note that it is possible to change what people are working on too often, since switching tasks is costly. Parallelizing work on the top few priorities, as mentioned above, helps with this, since if you decide that priority #3 is now #1, but there are 2 people working on each, then nobody has to switch tasks. The thing that kills you is when no one is working on the new priority #1.) Overcommunicate It’s not just enough for me personally to be running a fast OODA loop—in a large group, everyone needs to be autonomously making frequent, high-quality, local prioritization decisions, without needing a round-trip through me. To get there, they need to be ambiently aware of: what else is going on around them, so they can coordinate and update on new info quickly (“oh, we’re planning to kick off the next derisking run in three days, so I have to have my new RL environment ready and tested by then”) how their goal fits into the overall project, so they can make correct decisions about the details of their approach (“we’re trying to scale up as much as possible right now, so this direction isn’t valuable to pursue since it could never provide the scale of data we need”) I’ve usually found that to create the right level of ambient awareness, I have to repeat the same things way more often than I intuitively expect. This is roughly the same “communicate uncomfortably much” principle above, but applied to broadcasts and not just 1:1 conversations with people. For example, although the first team I managed at Anthropic started with a daily asynchronous standup, we found that synchronous meetings were much more effective for creating common knowledge and reorienting, so we moved to a twice-weekly synchronous standup, which probably qualified as “uncomfortably much” synchronous communication for Anthropic at the time. Break off subprojects Once a project gets over maybe 10 people, I can’t track everything myself in enough detail to project-manage the entire thing myself. At this point, it becomes critical to delegate. Here I mean delegating the project management, not just the execution (that’s what I’d be delegating to the first 10 people). This is the point where I need other people to help split up the work, monitor and communicate progress, escalate blockers, etc. A few things I try to keep in mind when delegating project management: The ideal unit of delegation is a crisp, simple, high-level goal, with limited overlap with other workstreams. (This is as opposed to, e.g., a list of tasks like “see if X helps.“) Good examples: “get X training technique working over Y networking protocol at Z throughput,” “get identical evals between model implementations A and B.” Bad examples: “follow this 10-step checklist that we hope results in training working,” “try these 3 techniques for debugging the loss eval.” The best project-managers are often not the strongest technical ICs. Instead the most important traits are that they’re highly organized and great at staying laser focused on end goals, perhaps to the point of being annoying about it. IC depth helps and I’ll never say no to it, but it’s not what I’d optimize for. People running subprojects are probably also doing a lot of the same stuff I do, in particular e.g. spending a lot of time on it. That means they’ll take a substantial hit to their IC productivity. This is expected, and is often worth it. “Direction is more important than magnitude”—it’s usually better to have a lower-velocity project that works on the right things, than a higher-velocity one that’s pointed at the wrong goal. One of my favorite things to make delegation easier is to keep goals simple—if they can fit in a Slack message while still crisply describing a path to the desired end state, then the people working on the goal will be much more able to prioritize autonomously, and point their work at the real end goal rather than doing something that turns out to be useless for some reason they didn’t think about. “Keep goals simple” doesn’t have to mean “do less”—the best way to keep goals simple is to find the latent structure that enables a clean recursive decomposition into subgoals. This often requires a deceptive amount of work—both cognitive and hands-on-keyboard—to identify the right intermediate goals, but I’ve found that it pays off immensely by clarifying what’s important to work on. Have fun Some of my favorite memories of Anthropic are of helping out with these big projects. While they can be intense, it’s also really inspiring to see how our team comes together, and the feeling of being part of a big team of truly excellent people cooking something ambitious together can be really magical! So I try to enjoy the chaos :) Appendix: my project DRI starter kit Here’s the internal doc I share with folks on my team who are getting into being responsible for large projects. So you’re the DRI of a project (or part of one). Concretely, what do you do to “be DRI”? This doc is my suggested “starter kit” answer to that question. The habits and rituals described here aren’t perfect for every situation, but they’re lightweight and broadly helpful. I suggest you use them as a starting point for iteration: try them out, then adjust as necessary. This is an SL init; the RL is your job :) Goals of this playbook The goal is to help you do your job as DRI— Make your project go quickly: Participants deeply understand the root goal and can autonomously choose the most important next things to work on People have “situational awareness” of what other people are working on, learn about relevant updates quickly, and coordinate quickly when needed People get quick feedback on their work If things aren’t going fast enough, you (the DRI) can notice and course-correct quickly “Play well with others:” Observers can figure out where to go to follow along Adjacent or intersecting people/projects don’t miss important updates or get caught by surprise People notice quickly if the project is behind or off-track, and can identify opportunities to help —without adding too much overhead: <1 hour of setup to make a working doc, schedule a weekly meeting, etc. 30 min/week of meetings 15-30 min/week to write an update (Note: being DRI will still unavoidably add some overhead—e.g. you’ll have to track what other people are doing, delegate work, unblock people, set and communicate goals, etc. The goal is specifically for the process/paperwork to be minimal.) Weekly meeting You should schedule at least one 30-minute weekly meeting with everyone working on the project. The goal of this meeting is to (1) be a backstop for any coordination that needs to happen and didn’t happen asynchronously; (2) be an efficient way to create common knowledge of goals, updates, etc.; (3) help you track whether things are going well. Starter-kit agenda: [5m] DRI reviews major updates from last week and sets goals for next week [10m] Silent write and comment on discussion topics [10m] Synchronous discussion of most important things not addressed during silent write Signs that more meetings might help (e.g. a second weekly standup): you have a very tight deadline and can’t afford to lose time people aren’t working on the most important thing people need feedback frequently people step on each others’ toes or miss opportunities to help each other out if you just like hanging out with each other :) Landing page / working doc It’s really helpful for discoverability and wayfinding to have a single “master doc” with all the most important info about a project. As you loop more people in, they can read the doc to get up to speed. And anyone who thinks “I wonder how X is going” can stop by there to find out. Create a doc for your workstream with: A go/ link in the name (if a subproject, maybe use go/project/subproject) → This makes it easier to find quickly (search is kinda rough) A clear description of a concrete top level goal and how it fits into broader goals → This is critical info for participants, so they can autonomously prioritize the most important things; and for observers, so that they know what outcome to expect. Staffing: A list of people working on the project, your name as the DRI, and a link to the slack channel that’s being used for discussion Links: A short list of relevant links at the top (work trackers, the project’s Slack channel, major design docs, etc.). If needed, a longer “docs / see also” section later links to relevant docs. → It’s really easy to lose track of relevant docs otherwise! A roadmap section with intermediate goals and target dates → See the section on plans; these will help people understand what the overall shape of the project is expected to be. A section for “running notes” containing meeting notes from your weekly meetings (and any other ad-hoc meetings) and broadcast updates → This really helps observers and new-joiners get up to speed! I like maintaining a list of important open questions / uncertainties/ risks and updating it over time. This helps me stay focused on removing risk from the project as quickly as possible. If it’s part of a larger project, your doc should be nested within the larger project’s working doc. If this ends up being too much for one doc, you can fork these out into sub-docs (esp. running notes and updates). Plan / roadmap / milestones In your working doc, include a section with some intermediate goals and dates by which you hope to accomplish them. → This is helpful mostly for noticing you’re off track or behind without getting frog-boiled. → Or noticing when you need to make a direction change because the intermediate goals don’t seem good anymore. You might feel some pressure to add false certainty or precision, but avoid this and be honest about your uncertainty instead. For a lot of research projects it’s hard to plan more than a couple weeks ahead. You can make the milestones fuzzier / more aspirational beyond that, or just drop them. I often find it helpful to phrase milestones in probabilitis and distributions (e.g. “my 90% confidence interval for this date is X-Y” or “I think there’s a 75% chance this technique works”) Who’s working on what You should have something somewhere that describes what people are working on. The minimum viable version of this is a list of what people are working on in your working doc. If you end up with a large set of tasks and a big backlog, maybe use a checklist and/or move to a subdoc. Stack rank your work list. It’s really important for people to understand priorities! If there’s more different people/TODOs, I suggest using some app to make a kanban board with “backlog” / “up next” / “in progress” / “done” columns. This is probably most helpful for more deterministic/plannable projects where there’s a clear backlog + set of future tasks, and a lot of things you need to remember to do. If you have an external task tracker, link it in the wiki section of the working doc. Slack norms Have conversations about the project in a Slack channel (not DMs). Reference the channel in your working doc. Link the working doc in the Slack channel bookmarks. Cross-post notebook posts and experiment write-ups into the channel so observers don’t have to follow tons of notebook channels. Do not use DMs. These make it hard to make info discoverable or share it further. If people send you important stuff in a DM, ask them to put it in the project channel. If you need confidentiality, make a private channel. Avoid centithreads. Most ≥10-message Slack threads would be better as a ~5-minute Tuple. (This is hard to do with people who are in tons and tons of meetings like execs. But you should try to do it for others.) If you end up with a centithread, assume nobody will read it; post a summary back to the channel afterwards. Bias towards fewer, larger, noisier channels. The right time to create a channel is when discussion is either not happening, or getting lost. → Too many slack channels makes it harder to manage membership, decide where to put things, or find where discussion is happening. Channel organization and membership matters. Invest in routing conversations to the right place and curating the channel “architecture.” Weekly broadcast updates Once a week, probably either just before or just after your weekly meeting, write up a brief update for a broader audience with: The overall vibe What’s changed since last update What’s coming up next When writing these updates, optimize for signal to noise ratio. Err towards concision No “we worked on X”—tell me “we accomplished Y” or “we learned Z” Remember your audience (= people not familiar with the project) State things crisply and concretely (“X improves eval Y by Z points,” not “we got X working”) Leave out anything that’s not actionable—you don’t need to be exhaustive Post the update in your project Slack channel, and cross-post it to other relevant channels (e.g. a larger “megaproject” channel) if necessary. If your project is part of a larger megaproject, these updates might feed into something broader like a weekly meeting of DRIs or an aggregated status update. Retrospectives Every so often, step back and ask “how could the last X weeks have gone better?” Frequency depends on how much there is going on—every 2 weeks is good if there’s a lot, maybe every 4-8 weeks for smaller projects Suggested meeting format Friday afternoon [13 min] Async brainstorm 2 lists of items: “what went well” / “what we could improve” [2 min] Dedupe topics and emoji vote by putting :heavy_plus_sign: next to ones you agree with Sort “what we could improve” by highest votes [10 min] Synchronous discussion of top points (either highest voted or flagged by DRI); figure out action items Thanks to Kelley Rivoire for many thoughtful comments on a draft!

This is an adaptation of an internal doc I wrote for Anthropic. I’ve been noticing recently that often, a big blocker to teams staying effective as they grow is trust. “Alice doesn’t trust Bob” makes Alice sound like the bad guy, but it’s often completely appropriate for people not to trust each other in some areas: One might have an active reason to expect someone to be bad at something. For example, recently I didn’t fully trust two of my managers to set their teams’ roadmaps… because they’d joined about a week ago and had barely gotten their laptops working. (Two months later, they’re doing great!) One might just not have data. For example, I haven’t seen most of my direct reports deal with an underperforming team member yet, and this is a common blind spot for many managers, so I shouldn’t assume that they will reliably be effective at this without support. In general, if Alice is Bob’s manager and is an authority on, say, prioritizing research directions, Bob is probably actively trying to build a good mental “Alice simulator” so that he can prioritize autonomously without checking in all the time. But his simulator might not be good yet, or Alice might not have verified that it’s good enough. Trust comes from common knowledge of shared mental models, and that takes investment from both sides to build. If low trust is sometimes appropriate, what’s the problem? It’s that trust is what lets collaboration scale. If I have a colleague I don’t trust to (say) make good software design decisions, I’ll have to review their designs much more carefully and ask them to make more thorough plans in advance. If I have a report that I don’t fully trust to handle underperforming team members, I’ll have to manage them more granularly, digging into the details to understand what’s going on and forming my own views about what should happen, and checking on the situation repeatedly to make sure it’s heading in the right direction. That’s a lot more work both for me, but also for my teammates who have to spend a bunch more time making their work “inspectable” in this way. The benefits here are most obvious when work gets intense. For example, Anthropic had a recent crunch time during which one of our teams was under intense pressure to quickly debug a very tricky issue. We were able to work on this dramatically more efficiently because the team (including most of the folks who joined the debugging effort from elsewhere) had high trust in each other’s competence; at peak we had probably ~25 people working on related tasks, but we were mostly able to split them into independent workstreams where people just trusted the other stuff would get done. In similar situations with a lower-mutual-trust team, I’ve seen things collapse into endless FUD and arguments about technical direction, leading to much slower forward progress. Trust also becomes more important as the number of stakeholders increases. It’s totally manageable for me to closely supervise a report dealing with an underperformer; it’s a lot more costly and high-friction if, say, 5 senior managers need to do deep dives on a product decision. In an extreme case, I once saw an engineering team with a tight deadline choose to build something they thought was unnecessary, because getting the sign-off to cut scope would have taken longer than doing the work. From the perspective of the organization as an information-processing entity, given the people and relationships that existed at the time, that might well have been the right call; but it does suggest that if they worked to build enough trust to make that kind of decision efficient enough to be worth it, they’d probably move much faster overall. As you work with people for longer you’ll naturally have more experience with each other and build more trust. So on most teams, these kinds of things work themselves out over time. But if you’re going through hypergrowth, then unless you’re very proactive about this, any given time most of your colleagues will have some sort of trust deficit. Symptoms I sometimes notice that can indicate a buildup of trust deficits: Too many decisions needing to be escalated Too many decisions requiring deep involvement from many stakeholders People having lots of FUD about whether projects they’re not involved in are on track Leaders frequently needing to do “deep dives” on individual topics Leaders needing to spending most of their time working “in the system” (problem-solving specific issues) rather than “on the system” (unblocking future growth) Hiring more people doesn’t make you (much) less busy It’s easy to notice these and think that the solution is for people to “just trust each other more.” There are some situations and personalities where that’s the right advice. But often it’s reasonable not to trust someone yet! In that case, a better tactic is to be more proactive about building trust. In a large, fast-growing company you’ll probably never get to the utopian ideal of full pairwise trust between everyone—it takes too long to build. But on the margin, more effort still helps a lot. Some ways to invest more effort in trusting others that I’ve seen work well: Share your most important mental models broadly. At Anthropic, Dario gives biweekly-ish “informal vision updates” (hour-long talks on important updates to parts of company strategy) that I think of as the canonical example of this. Just about everyone at Anthropic is trying to build an internal “Dario simulator” who they can consult when the real one is too busy (i.e. ~always). For high level strategy, these updates do an amazing job of that. Put in time. In addition to one-way broadcasts, trust-building benefits a lot from one-on-one bidirectional communication so that you can get feedback on how well the other person is building the right models. This is one of the reasons I schedule lots of recurring 1:1s with peers in addition to my team. Offsites are also very helpful here. Try people out. If you’re unsure whether someone on your team will be great at something, try giving them a trial task and monitoring how it’s going more closely than you would by default, to catch issues early. This is a great way to invest in your long-term ability to delegate things. Give feedback. It’s easy to feel like something is “too minor” to give feedback on and let it slide, especially when there’s always too much to do. But I’ve never regretted erring on the side of giving feedback, and often regretted deciding to “deal with it” or keep quiet. One pro-tip here: if you feel anxious about giving someone negative feedback, consider whether you’ve given them enough positive feedback—which is a helpful buffer against people interpreting negative feedback as “you’re not doing well overall.” Inspection forums, i.e., recurring meetings where leadership monitors the status of many projects by setting goals and tracking progress against them. The above tactics are mostly 1:1 or one-to-all, but sometimes you want to work with a small group and this is an efficient way of doing that. To help other people trust you: Accept that you start out with incomplete trust. When someone, say, tries to monitor my work more closely than I think is warranted, my initial reaction is to be defensive and ask them to trust me more. It takes effort to put myself into their shoes and remind myself that they probably don’t have a good enough model of me to trust me yet. Overcommunicate status. This helps in two ways: first, it gives stakeholders more confidence that if something goes off the rails they’ll know quickly. And second, it gives them more data and helps them build a higher-fidelity model of how you operate. Proactively own up when something isn’t going well. Arguably a special case of overcommunicating, but one that’s especially important to get right: if you can be relied on to ask for help when you need it, it’s a lot less risky for people to “try you out” on stuff at the edge of what they trust you on. Related reading: Inspection and the limits of trust