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!

This post was adapted from an internal doc I wrote at Wave. Welcome to being a manager! Your time-management problem just got a lot harder. As an IC, you can often get away with a very simple time-management strategy: Decide what your one most important thing is. Work on it until it’s done. GOTO 1 As a team lead, this isn’t going to work, because much more of your work is interrupt-driven or gets blocked for long periods of time. One-on-ones! Code reviews! Design reviews! Prioritization meetings! Project check-ins! All of these are subject to an external schedule rather than being the type of thing that you can push on in a single focused block until it’s done. Being a team lead means three big changes for your time management: You no longer have a single most important thing. You’ll have to learn how to juggle competing priorities. Your most important responsibility is for your team’s output, not your personal output. That means that individual engineering work goes last in your list of potential most important things. You’ll need to start spending some of your time on a manager’s schedule: There are two types of schedule, which I’ll call the manager’s schedule and the maker’s schedule. The manager’s schedule is for bosses. It’s embodied in the traditional appointment book, with each day cut into one hour intervals. You can block off several hours for a single task if you need to, but by default you change what you’re doing every hour. Most powerful people are on the manager’s schedule. It’s the schedule of command. But there’s another way of using time that’s common among people who make things, like programmers and writers. They generally prefer to use time in units of half a day at least. You can’t write or program well in units of an hour. That’s barely enough time to get started. Here’s some advice on how to cope with those changes. Have accurate expectations of yourself Your responsibilities to your team will take time, and even more importantly, attention. That means you’ll be a lot less productive on IC work than you have been in the past—especially at first while you’re finding your legs. Additionally, your time will be less predictable week-to-week as you might have to spend an unknown amount of time responding to “inbound” work. For the first few months, you should treat any individual engineering work that you get done as a bonus. Even after that, you should expect to have something like 10-20% less individual output per engineer you manage, depending on how experienced you are, they are, etc., and with substantial week-to-week variance. To mitigate this, my rule for myself has been to make sure that my IC work is important but not urgent—i.e. that nobody will be sad and no plans will be derailed if I end up having to spend the next week firefighting instead of pushing it forward. For honing my intuitions about how much I can actually expect to accomplish, I’ve found time tracking very useful (see How time tracking helped me be a better manager and I apparently got 50% better at my job last month). Prioritize ruthlessly A corollary of the above is that it becomes very important for you to prioritize what to work on, both on an hour-to-hour cadence and on a larger timescale. It’s not possible to write down a full algorithm for prioritizing in a blog post—that’s why they pay us the big bucks—but here are some heuristics for which things are most worth prioritizing: Deadlines where something bad happens if you miss them. (e.g. performance improvements in advance of a holiday rush.) Note that the badness of missing deadlines varies wildly. Make a habit of asking “what is the reason for this deadline?” for any deadline-driven project. Work that increases your or your team’s future bandwidth. This can include hiring, addressing tech / process debt, automating toil, mentoring people, reducing pager burden, etc. A useful way of thinking about it is to rank this kind of work based on the “payback period,” or how long it takes before the time saved by the improvement exceeds the time invested in making it. One-on-ones. Try very hard not to cancel these, unless you’re on vacation—the other 39.5 hours a week they’re focused on what you need from them, so please don’t disdain the 0.5 hours you spend focused on what they need from you. If you cancel too many, expect your reports to feel less safe bringing up tricky things, and to have more issues “blow up” because they didn’t get addressed early. Unemploy your future self One of the most important types of “work that increases your or your team’s future bandwidth” is delegating things. This is something entire books have been written about, but here’s how to avoid a few common delegation pitfalls for new team leads: Negotiate how hands-on to be. Effective delegation means finding the right balance between micromanaging, and throwing your report to the wolves. The stereotype is that new managers often micromanage, but at Wave, I’ve noticed that new managers often err on the side of undermanaging, or being too hands-off, perhaps out of a desire to signal that they trust their reports. If you’re unsure, it’s good to have an explicit conversation with the person you’re delegating to about how much support they want. E.g. “do you want to do the design for this feature yourself, have me do the high-level and fill in the details, or have me write the entire design doc?” Calibrate to your team members’ task-relevant maturity, or how capable they are of independently doing a particular type of task. A senior engineer should be able to design most features independently (with review), but give the same design task to a junior engineer and they’ll probably flail around and make no progress. You should be maintaining a mental map of each of your team members’ strengths and weaknesses—and updating it over time as you help them improve. Delegate ahead of future growth. Your team’s workload is going to increase over time, so even if you don’t feel like you have too much work to do right now, you probably will in the future, unless you currently feel underutilized. You should aim for a workload where in the steady state, you feel like you have some slack capacity. Delegate “stretch projects” to help your team level up. Getting enough slack might require you to delegate work that no one else on your team can currently do. Take your mental strengths-and-weaknesses map, ask yourself what the most important growth directions for each of those team members are, and figure out how to give them work that stretches them in that direction. Note that these delegations will probably require more frequent monitoring, since your reports will have less task-relevant maturity on their stretch projects! A five-step “help, I’m overwhelmed” checklist Despite your best efforts to follow the above advice, there will probably come a time when you feel very stressed about the amount of work on your plate. When that time comes, here’s what to do: Schedule time with your manager, for the soonest slot you can, to triage your todo list. (If the primary stakeholder for your scariest todos is your PM, schedule with them instead.) Make a list of everything that’s on your plate currently. Yes, everything, even that code review that’s been sitting in your backlog for the last 3 months. At the meeting you scheduled in step 1, figure out how to delegate everything in that list you can delegate, then stack-rank the remainder. Realistically (see Have accurate expectations of yourself) decide how far down the list you’re going to get. Remember to leave yourself some slack for whatever comes up! For things below the cutoff, decide that you’re not going to do them, and notify everyone who cares that you probably won’t get to it. Carve out focused time If you’re not careful, it’s easy to fill your entire calendar with meetings, Slack, etc. and have no time for deep work. With careful planning, you can avoid this by “batching” all your distractions to particular times of day. There are lots of tactical tips for doing this; I catalogued some that work for me in Tools for keeping focused. One tech-lead-specific one that I’ll add is batching meetings: I schedule all my meetings back-to-back on Tuesdays and Thursdays to leave the rest of the week as free as possible for deep work. Appendix: further reading Rest in Motion How time tracking helped me be a better manager Time management: the leadership meta-problem. Tools for keeping focused Attention is your scarcest resource I apparently got 50% better at my job last month The Top Idea in Your Mind Maker’s Schedule, Manager’s Schedule My weekly review habit

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