Full Width [alt+shift+f] Shortcuts [alt+shift+k]
Sign Up [alt+shift+s] Log In [alt+shift+l]
45

iPad in 2020

from Dustin Curtis [alt+shift+b] in startups

A couple of months ago, I switched entirely to an iPad Pro for about two weeks. I did not use my MacBook Pro at all, and forced myself to do everything on the iPad. After that experience, I planned to write some kind of review, but it turned out that my conclusions were pretty simple: iPad Pro running iOS 13 can technically do almost everything a MacBook Pro can, but it is incredibly frustrating to use. Accomplishing anything other than trivial tasks takes 2-5x longer with 10x more cognitive overhead than on a Mac. iPadOS is simply an annoying operating system to use. The iPad is amazing for content consumption and certain types of gaming, but no matter how much Apple pundits might try to say the iPad is a device well-suited for “creation,” it just isn’t – unless you are an artist using Apple Pencil. And so, as the iPad turns ten years old this week, I agree with John Gruber’s assessment. In The iPad Awkwardly Turns 10, he writes: […] I don’t think the iPad has come close to living up to its potential. By the time the Mac turned 10, it had redefined multiple industries. In 1984 almost no graphic designers or illustrators were using computers for work. By 1994 almost all graphic designers and illustrators were using computers for work. The Mac was a revolution. The iPhone was a revolution. The iPad has been a spectacular success, and to tens of millions it is a beloved part of their daily lives, but it has, to date, fallen short of revolutionary. […] Software is where the iPad has gotten lost. iPadOS’s “multitasking” model is far more capable than the iPhone’s, yes, but somehow Apple has painted it into a corner in which it is far less consistent and coherent than the Mac’s, while also being far less capable. iPad multitasking: more complex, less powerful. That’s quite a combination. Complex, but less powerful. The result is something workable but annoying to use. I hope that separating iPadOS from iOS indicates that Apple is going to devote more resources toward...
28th Jan 2020

Stay updated

Get a weekly newsletter with the top 5 articles worth reading every week.

More from Dustin Curtis

Thoughts on thinking

I have been stuck. Every time I sit down to write a blog post, code a feature, or start a project, I come to the same realization: in the context of AI, what I’m doing is a waste of time. It’s horrifying. The fun has been sucked out of the process of creation because nothing I make organically can compete with what AI already produces—or soon will. All of my original thoughts feel like early drafts of better, more complete thoughts that simply haven’t yet formed inside an LLM. I used to write prolifically. I’d have ideas, write them down, massage them slowly and carefully into cohesive pieces of work over time, and then–when they were ready–share them with the world. I’d obsess for hours before sharing anything, working through the strengths and weaknesses of my thinking. Early in my career, that process brought a lot of external validation. And because I think when I write, and writing is how I form opinions and work through holes in my arguments, my writing would lead to more and better thoughts over time. Thinking is compounding–the more you think, the better your thoughts become. But now, when my brain spontaneously forms a tiny sliver of a potentially interesting concept or idea, I can just shove a few sloppy words into a prompt and almost instantly get a fully reasoned, researched, and completed thought. Minimal organic thinking required. This has had a dramatic and profound effect on my brain. My thinking systems have atrophied, and I can feel it–I can sense my slightly diminishing intuition, cleverness, and rigor. And because AI can so easily flesh out ideas, I feel less inclined to share my thoughts–no matter how developed. I thought I was using AI in an incredibly positive and healthy way, as a bicycle for my mind and a way to vastly increase my thinking capacity. But LLMs are insidious–using them to explore ideas feels like work, but it’s not real work. Developing a prompt is like scrolling Netflix, and reading the output is like watching a TV show. Intellectual rigor comes from the journey: the dead ends, the uncertainty, and the internal debate. Skip that, and you might still get the insight–but you’ll have lost the infrastructure for meaningful understanding. Learning by reading LLM output is cheap. Real exercise for your mind comes from building the output yourself. The irony is that I now know more than I ever would have before AI. But I feel slightly dumber. A bit more dull. LLMs give me finished thoughts, polished and convincing, but none of the intellectual growth that comes from developing them myself. The output from AI answers questions. It teaches me facts. But it doesn’t really help me know anything new. While using AI feels like a superhuman brain augmentation, when I look back on the past couple of years and think about how I explore new thoughts and ideas today, it looks a lot like sedation instead. And I’m still stuck. But at least I’m here, writing this, and conveying my raw thoughts directly into your brain. And that means something, I think, even though an AI could probably have written this post far more quickly, eloquently, and concisely. It’s horrifying. This post was written entirely by a human, with no assistance from AI. (Other than spell- and grammar-checking.)

16th May 2025 • 1 votes
It is link winter on X

We do not know how, why, or when the X algorithm devalues posts with links, but it does—without telling you, and by a lot—and it makes the experience there worse. Without links, information on X is headlines without stories, commentary without context, magic without the prestige. We do not know by how much the inability to share or see source links has impacted the spread of misleading or incorrect information, but we do know that primary sources cannot be put into X posts and that replies with links are shown to 70-90% fewer people. Speech on X is free, but only if you reference other speech on X. In Laos, I once asked a rural villager how he determined the truth, given that the government restricted his media to their controlled outlets. He thought for a few minutes, looked around, became confused, and then said, “Isn’t the truth what the government says?” The truth on X is what random people commentate, polarize, interpret, and summarize from source material that is intentionally lost by a black box algorithm. There is no depth to anything on X because context with links is heavily penalized. This is bad for humanity and the opposite of free speech. It is link winter on X.

5th Dec 2024 • 96 votes
Tesla and Storytelling

Last week, Tesla unveiled two world-changing products: Robotaxi1, a fully self-driving taxi with no steering wheel or pedals, and an autonomous humanoid robot, called Optimus2, that can walk and has fully functioning hands and feet. Both of these products have been depicted in science fiction for decades, so the fact that a company is working on them was not surprising. What was surprising is that Tesla showed them existing today. The event looked and felt like a major product launch; they had clearly spent an incredible amount of time and effort to redecorate the 20-acre Warner Bros. studio backlot with a futuristic theme. In front of a couple thousand attendees, Elon Musk walked on stage and quickly showed off the new vehicles and robots while making very brief remarks about autonomy and the future of parking lots. Then he announced it was time to party, and walked off the stage. I was extremely confused. No products were launched. No details were shared about the Robotaxi or the Optimus robot. He raised a thousand questions and answered only one: when asked when Robotaxi would ship, Musk stumbled over himself as though he’d never thought about the answer before, and then appeared to make it up on the spot: “before 2027”. In other words, these products were not products: they were concepts. And while a lot of progress has recently been made on driverless cars and autonomous robots, for now (with few exceptions) they are still firmly in the realm of science fiction. Usually, when a company puts on a production this large, there’s a reason. When Apple announces its new operating systems or iPhones, they show off the new features and share when they’ll be available. But Tesla’s event seemed to have no purpose. Musk did not go into detail about features, design, or availability. In fact, the products he showed cannot even exist in the real world as they were presented. The Optimus robot hardware is extremely impressive, but the demo machines were surreptitiously and fully controlled by remote human operators. The Robotaxi relies on near perfect self-driving reliability, but the software for that doesn’t exist yet at Tesla, either. The demo units were half impressive engineering, half illusion. The choice of a movie set as the event’s venue was perfect. What I found most confusing was that Tesla gained nothing from showing off these concepts. They won’t be available to buy for years, and by then there will have been many more iterations. In the end, what they did accomplish was to throw an elaborate party for a small number of attendees, who were able to interact with a theme park-like vision of the future, while the millions of people who streamed Musk’s presentation were given an unorganized, disjointed misrepresentation of the state of the art. Tesla and Musk had a rare opportunity to use the event as an inspiring statement of mission and purpose. They could have told a story about why Tesla exists, why it is working on these products in particular, and how everything fits into the tapestry of the company’s overall mission. Musk could have explained that the Robotaxi has always been part of Tesla’s ambitious “master plan,” and then given a progress update on how the plan is being executed while showing the demo vehicles and robots. That would have been something worth watching and a story worth telling. But Musk didn’t tell that story. He showed off half-finished products and then threw a party. Over the years, I’ve come to believe that being able to put whatever you’re working on into the context of a bigger story is as important as making it work well–whether it’s a building, a company, an essay, a piece of software, or a hamburger. Good storytelling is good craftsmanship. Without a good story, without clear context and purpose, it’s hard to maintain the essence of a thing, and far too easy to make poor design decisions. When you develop the full story behind why and how you’re building something, you can make decisions based on principle instead of opinion, and if you can communicate that story well to others, you can way more easily get them to understand your vision. This applies to everything from product development to sales and marketing. The products Tesla has been working on are undeniably inspiring objects of a very optimistic future. Most companies focus on at most the next few iterations of their products, but Tesla is unique in that it defines the future for itself and then pulls it kicking and screaming into the present. Electric cars were impractical/impossible, and then Tesla made them ubiquitous. Humanoid robots have always been confined to science fiction, but Tesla is going to make them, too. The way Tesla operates is an inspiring story in and of itself. However, by announcing concept products years and years in advance, without providing context, especially while maintaining a wildly imaginative understanding of time, Tesla is damaging its reputation. Without a story, Tesla’s actions seem haphazard and erratic. Why did they throw a party instead of telling a good story? It makes no sense to me. Buried somewhere beneath its flamboyantly inarticulate product announcements, Tesla has one of the greatest and most inspiring stories in history. They are just awful at telling it. Musk variously and repeatedly refers to it as Robotaxi, Cybercab, and Cybertaxi. I think names are important, so I used the one on Tesla.com. ↩ Technically, Optimus was “revealed” a few years ago at a very bizarre presentation–even for Elon Musk–during which a human, dressed like a robot, performed an interpretive dance. ↩

14th Oct 2024 • 106 votes
Luxury for everyone: thoughts on Vision Pro and Apple's DNA

In 2009, Microsoft released an enormous 200lb coffee table with an embedded 30-inch touchscreen called Surface. Although the iPhone had been around for a little while, the larger screen made Surface feel absolutely futuristic: in the Photos app, you could toss around pictures like they were physically in front of you. It cost $10,000. Very few people ever bought it. A little more than a year later, Apple released the $499 iPad. Microsoft had made a $10,000 table for no one, and Apple made a $499 tablet for everyone. This is a common theme among Apple’s most important products. They are usually built around existing ideas and technologies that have been improved and then repackaged into beautiful, premium experiences which are expensive but not unaffordable. This happened with the iMac, iPod, iPhone, iPad, and Apple Watch. Whatever the product, Apple has always brought seemingly impossible levels of quality and craftsmanship to the masses. Apple is luxury for everyone. Apple Vision Pro, however, is different. Yes, it is an undeniably beautiful product, and the software is very impressive. When I first used it, I was overcome with a sense of awe that I haven’t felt since seeing kinetic scrolling on the first iPhone. But Vision Pro costs nearly $4,000 and has enough faults that it still feels a bit like a technology demo. It is not affordable at all, and it brings nothing to the masses. Vision Pro feels bizarrely un-Apple in a way that only a few products have before, like the 18-karat gold Apple Watch, the $700 Mac Pro wheels, or the $1,000 Pro Display XDR stand. These recent Apple products are shameful Veblen goods that do not offer value commensurate with their price. And while the raw technology in Vision Pro is perhaps worth $4,000 today, I do not think it delivers nearly $4,000 in value. This is the exact opposite of most other transformative Apple products. So what happened? Good product design is a careful dance between what’s best and what’s possible. For the iPhone, building the right combination of technology and software at a practical price point was an enormous challenge that Apple pulled off. But it took years and years of development for the required technology in the iPhone to reach a price that was suitable for the market. When things were cost-prohibitive, the designers of the iPhone found clever workarounds or made hard trade-offs. The first iPhone wasn’t a perfect product, but it was designed against reasonable constraints. I don’t think Vision Pro was designed against reasonable constraints. If the goal was to make the equivalent of the iPod in a sea of mediocre MP3 players, Vision Pro hasn’t succeeded. It isn’t a disruptive VR headset because it isn’t even in the same market as its competitors, the majority of which are ten times cheaper. The goal, then, must have been to make a totally new product segment that only incidentally resembles the current VR market. Apple hints at this strategy by calling Vision Pro a “spacial computer.” The problem here is that if a spacial computer can’t be made today for under $4,000, then the technology simply isn’t ready. In its current state, I think Vision Pro is antithetical to Apple’s DNA: it isn’t accessible to most people, it is large and inelegant, and the platform itself has nebulous use cases. Design Philosophy # In my experience, whether it is hardware or software, there are two fundamental ways to approach product design. The first (and most common) philosophy is to build from the bottom-up, which involves assembling low-cost and basic components first, and then working to build up from those components to an experience that reaches a desired price-quality equilibrium. The second philosophy starts the other way around, by considering the maximum reasonable quality of an experience first–even if it is impractical–and then working over iterations to build down the product until it reaches an acceptable experience-cost equilibrium by making careful trade-offs and cleverly working around constraints. An example of a bottom-up product is the Amazon Kindle, which is made of inexpensive, flimsy injection-molded plastic and shows no signs of craftsmanship – it simply does what it says it will do. On the other hand, consider the Apple Watch, which is, even without its electronics, a beautiful object. It takes only a few moments of touching the watch case to realize that an incredible amount of thought was put into the materials, angles, and curves, and that perhaps even novel manufacturing techniques had to be invented to construct it. The top-down approach is more expensive and takes longer, but – as long as you have reasonable constraints and goals – the quality of the output is exponentially better. Apple Vision Pro seems to have subscribed to neither of these approaches, or its designers started with the top down approach and then gave up before hitting a reasonable equilibrium. It’s both absurdly expensive and has extreme tradeoffs that don’t seem to hit any cohesive product design strategy that would make it a great standalone product. It also has strange extraneous features like EyeSight, which must be incredibly expensive for what it accomplishes (rather poorly). What was the purpose of launching Apple Vision Pro now, when it is incapable of bringing anything new to the masses? It’s not luxurious, even though it’s well constructed. And at its current price, it’s definitely not for everyone. Essentially, it’s an expensive tech demo. Apple’s other groundbreaking products, like iPod, iMac, iPhone, and Apple Watch were all very focused products that launched with reasonable features at reasonable prices. They relied on Apple’s soul to guide their development. Vision Pro, it seems, not so much. Apple’s DNA and culture used to drive the company to make $499 tablets for everyone – a feat that seemed impossible at the time. But today, like the $10,000 Surface Table in 2009, Apple now makes a $4,000 headset for no one.

21st May 2024 • 171 votes
Contribution and abundance

Ben Horowitz gave this remarkable response to a question about joy and happiness on Time Well Spent: In my experience there are really two things that lead to happiness and everything else is mostly noise. The two things are contribution and abundance. Contribution is basically exactly as it sounds. If you can align your life with where you have the talent to make a large, meaningful, and real contribution to the world, your circle, or your family, then you can be very happy. As an aside, doing so often leads to making money because when you create great value like Elon Musk, you get a lot in return. Now, that doesn’t mean you have to be a business person to be happy, because happiness comes from the knowledge and impact of the contribution rather than the reward. However, this doesn’t quite work by itself, which brings me to the second point: abundance. An easy way to think of abundance is that it’s the anti-hater/anti-jealous mindset. If you believe there is plenty in the world for everyone and you are always happy to see people who contribute succeed, then you become part of “team contribution.” You don’t worry that someone is getting ahead of you at work or that someone made a lot of money or that someone is better looking than you, because you believe in abundance over scarcity and you can focus on maximizing your contribution. In fact, their joy can become your joy (then you have an abundance of joy :-)). The good news is that abundance is actually true. There is plenty in the world for everyone and once you see that, there are so many ways to contribute. I visited a Syrian refugee camp in Jordan a few years ago. On the way to the camp, there were a few refugee families not even in the camp but in some tents on the way. The area was completely barren. No plants, no trees, no grass… just rocks. So here’s this extended family of about 20 living in this tent on rocks, because their farm was destroyed by the war and they had to flee to Jordan. They were all living in this tiny tent. If anyone should have had a scarcity mindset, it was them. But I experienced the opposite. They immediately offered me a cup of coffee and some rice pudding (as if they had enough to share) and told me the whole story of their journey. What struck me the most was that they were genuinely happy despite what they went through. They were less incensed by getting bombed out of their homes than people in the U.S. are if you accidentally interrupt them. I’ve seen this kind of happiness through abundance in many countries: Cambodia, Haiti, Uganda… Those refugees were happier than some billionaires I know. That’s not to say that money doesn’t help… it does, but without an abundance mindset, it’s not enough. If, on the other hand, you have a scarcity mindset, it’s really hard to be happy no matter what you get or how rich you are or how good looking you are, because there’s always somebody richer or better looking or whatever. You become part of team “hate.” This is why you see so many deeply unhappy political activists. In theory, they should be making a massive contribution, but often they are just expressing hate for the other side. Hitler and Lenin are famous cases, but there are many, many more, because there’s a fine line between advocating for one group and hating the other group. If you’re doing the former like Martin Luther King Jr., you have an abundant view and will find joy in the work, but if you are doing the latter, you have a scarcity view. People with scarcity mindsets are always unhappy in my experience. Scarcity is not just in politics. You see it in business all the time. You see somebody stealing credit for someone else’s work or being deeply jealous about someone else’s promotion — these people are almost never happy. You even see it in the music industry or in sports. The quest to be the best turns into you not wanting anyone else to be the best. In these cases, even if you reach the pinnacle, there is no joy. Ben Horowitz The interview is worth reading in its entirety: The Architecture of Tomorrow.

4th May 2021 • 45 votes

More in startups

I did a meditation and it sort of changed my personality?!

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.”

yesterday • 1 votes
Are You Operating Out of Fear or Joy?

Scarcity and survival keep you from being your best.

5 days ago • 4 votes
The frontier labs launch election war rooms

An old playbook is back for the deepfake era. Is it working?

5 days ago • 1 votes
Running Dry

If you haven’t subscribed to Where’s Your Ed At, now’s the best time. I’ve extended the sale — 10% off of the $70-a-year subscription for life (click here!) — for new subscribers for another week. It’s a

6 days ago • 1 votes
Anthropic’s moat is Claude

The bull case for Anthropic’s IPO.

a week ago • 6 votes
📚 BoredReading

You seem to be enjoying this.

Join free to unlock everything.

Create free account

Already have an account? Sign in