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Jews do mourning well. That’s what I’ve always thought from watching family and friends go through it. It’s what I’ve learned as fact since my father died eleven months ago. There’s a central tension to it. A constant fault line that our customs straddle. It’s the constant struggle of an individual and a member of community. To be sure that’s one of the central themes of Judaism itself. We take responsibility for the commandments ourselves - each of one of us. But we do so many of them as a community. A person keeps kosher, shabbos, honors his parents. The community prays, builds, comforts and protects. I and Thou, sort of. 1 I found this pattern in the second after my father died. This isn’t where I get specific. But those moments are the loneliest in the world. Even with my mother and my siblings there. These moments are lonely not simply because they are but because our laws tell us that, at that moment, we are forbidden from completing the time bound laws of Judaism. These are ones that are so often tied to community. We cannot eat meals with friends and bless our food. We do not pray with a minyan. There is only one thing, to prepare for the funeral - really the burial itself. And so I sat alone - with other people, with my wife - but alone with my thoughts of my father. I chose to write a eulogy, though not everyone does. You are alone. But not for very long. In fact our laws say that you must do everything you can to bury the deceased before the next nightfall. You must do it with others. For a variety of reasons. The one that gives the most strength is that a burial means saying kadish means getting a minyan together to respond. At the least. I recently listened to a Jew who was raised in the USSR say that the only communal Judaism she knew as a child was when 11 men would gather secretly to say kaddish. 10 to make the minyan. 1 to watch out for the KGB. I was lucky in this. We had more than a minyan. We had a synagogue full to bursting with people who loved my father, or me, or my siblings or mother or who loved people who loved my father. He was easy to love. So I crossed - alone to community. Though you can be alone even surrounded by people. The first kaddish is lonely. At the graveside. But I could hear my brother and sisters and mother and the rabbi. I was lucky. It felt a little less lonely. 7 And then we come to Shiva, the “Seven”. Maybe the greatest thing we do though you only learn that when you are forced to do it. Our tradition does not allow you to be alone during the time that you want to be alone more than anything. It started after burial. That evening with a minyan at our house. I led services. Haltingly uncomfortably stumbling through words I mostly knew but hadn’t paid enough attention to in years. Though even there, the tension is constant. I was with other people, but I was also alone. Even saying the kaddish out loud requires you to chant words in dead language - aramaic - loud enough that others can hear you and respond. The constant thought is “what if I mess up.” The answer is that no one will notice and if they do they will give you comfort and gentle help. And you’ll do it. Each day our house filled with people and we told them stories and they told us stories. I’d speak to the room, and feel…not alone. My siblings and mother would speak, and I could feel the warmth of other people. There’s a beautiful and strange thing we say when we leave a house of shiva. “HaMakom yenachem et'chem b'toch shar avay'lay Tzion vee'Yerushalayim.” It effectively means “May God comfort you amongst all the mourners of Zion and Jerusalem.” In this case “you” is plural. Which begs a question: what if you are sitting shiva by yourself? Our rabbi explained - even when a mourner is alone, the spirit of the deceased is by his side. God is by his side. We’re never alone even when we want to be. There is always comfort. 30 After the shiva comes the strangest period of mourning, the Shloshim or “Thirty.” This liminal period contains many of the restrictions of shiva - no haircuts or shaves, no new clothes, limited interactions with groups, no parties. For me, the hardest part of it was going to minyan daily. Going three times per day. Leading nearly every service I attended which is meant as an honor but comes with the designation of being a “chiyuv” or a “requirement.” How strange it is to be in a room with people I often did not know and being told to get up in front of everyone, by myself, and lead services. How lonely. But, the response to the kaddish. The same everywhere every time. With warmth and feeling. The questions in each new place I went “Who did you lose? I’m so sorry, do you want to tell me about him?” What a forcing function we have to connect to our community to tradition to what we’d lost. Then one day shloshim ends. 11 The final period of active morning does not have a name I know. What I do know is that for the last 11 months I’ve done my best to go to minyan every day and say kaddish for my father. Usually I made it three times. One time I missed them all. I was lucky and I was determined. 11 months for various reasons though the one in my head is that all souls go to something like purgatory. We say kaddish to aid their progress to the world to come. Only the most evil of humans stay longer than 11. So we stop before the natural 12 months. My life rotated around finding places to go. Synagogues and offices and houses and one time a cafeteria that was empty. Each time it was a reminder to think of my dad. Each time I raised my hand to say “I’m chiyuv” I felt the fear of standing out, of being alone, of identifying myself. Of remembering that I was sad. Each time I did I was met with warmth and understanding. The ends of things sneak up on you. We thought - my siblings and I - that we’d finish kaddish this weekend. My brother did more research and found out that today is somehow the end. It echoes death. Sudden, unexpected. Less climactic than personally cataclysmic. A sundering and rupture and a quiet fall into the unknown. I’ll say kaddish as a mourner for my father for the last time this afternoon. The emotions are wildly complicated in ways I didn’t expect. Sad to lose this anchor, happy to be free of the requirement, curious what I’ll do with the flexibility. Mostly I miss my dad. But losing him bound me more tightly to the community I was born to and to the ones I’ve chosen and made. This is what our mourning does. It forces the individual to look within and then rebind himself to the many. It forces the many to look at the mourner and offer support and kinship and comfort and place. 12 The final moment of religious mourning will come in a month. It will come with its own struggles, its own moments. We know what to do with it, we have customs for it, for the yahrzeit, the anniversary. But that’s for later.
There are all kinds of strategies for evaluating startup ideas - investors talk about having a “prepared mind,” others build market maps, I like to think about toys, and we could go on. What everyone wants to do is predict the future. That’s honestly impossible. But we can pretend a bit and use hindsight as a framework to find the kinds of opportunities that are worth working on. We’re living through an example of how this could works thanks to generative AI. Roll the clock back five years and ask…just about anyone where they expected AI to have its first big impact. I’d imagine (at least I imagined at the time) most people would have said that AI would rise first in technical fields. We’d see leaps in biotech as computer minds outpaced human ones on drug design and discovery. We’d see vehicles capable of navigating themselves. We’d witness new materials and devices churned out by intuitively leaping machines. We wanted these things to be true because they’d be cool and also would produce huge financial returns. But we all knew, as we’d been told by countless works of fiction, that the creation of art would be the last realm to be conquered, that it would be the thing after AGI emerged because of how important the creative spark is to novel artistic endeavors. The patterns there don’t matter, we told ourselves; the soul is the thing. Whoops. In hindsight, of course the first truly breakthrough moments of AI came roaring out of creative fields - from art and from writing. The patterns were there, even if we pretended they weren’t. Look at a great photograph. It is not great at random. It is great because of the placement of elements in the frame, because of the balance of light and shadow, of negative and used space. Compare a photo from Henri Cartier-Bresson to the average selfie and your brain knows that one is great and one is bad even though you don’t know why. But feed a gazillion images to an AI and it will find those patterns once it can process enough of them. And then it can spit those patterns back out. The key to figuring this out, at least for an observer (and ok an investor and probably a founder thinking about what to do) is the hindsight bit. The English idiom has it that “Hindsight is 20/20” meaning that all the mistakes are only ever obvious when you’re looking backward. But we’re not looking for mistakes, we’re trying to figure out the next big thing. I don’t think anyone can accurately predict the future, but I think of this…hindsight game as the startup version of Albert Einstein’s Gedankenxperiments - his thought experiments that started with an impossible thing like “imagine you are riding a beam of light.” It’s a simple tool that most people will simply fail to either use or have enough imagination to find useful. It will also, probably, throw out lots of false positives. For thinking about technology and businesses, I find that the hindsight game looks a little something like this: take an idea that’s been presented to you. Rather than find all the things wrong with it, or the ways in which it will obviously be interesting but not huge, ask a simple question “what if everything about this is true, but only more so?” That’s the first part of the game. It requires you to imagine the future with one big change - don’t try to change everything, that’s too hard. Now, once you have that in your head, the next question is “ok, so what else is possible?” That’s the fascinating bit to me, not just what happens if X is true, but what Y exists only because X is true? It is fun to play this game with AI because of how fast the field is moving. So let’s work through a round of our game - let’s pretend that AI’s generative and analytical ability only gets better such that, in 5 - or 2 or 10 or 20 - years, it becomes painfully clear that there’s no such thing as a public market investor with an edge. The data is all public, the AI can analyze the data and run all kinds of scenarios and understand the relationship between all the assets and consider your needs and what’s logical and probabilistic and then spit out an ideal trade for you. But even that doesn’t matter much because there’s no alpha to any trade since the AIs are so fast and everyone has them. So what’s the point of active trading? Where do all the hedge funds go? Maybe they go poof and the real value accrues to the exchanges that figure out how to serve the AI trading mechanic and are now ludicrously valuable because stocks and bonds still need to trade. And then there’s a different kind of exchange because people like to gamble - but that exchange has an AI referee that looks for any unfair “edge” the way Call of Duty looks for cheaters. This could be totally wrong, but it’s coherent! Now you have hindsight. You have a model of how the world looks 5 years from now, looking back. What should you do now, knowing what’s to come? There’s no one answer to it, but it sure does open a lot of ideas on which to make some huge bets. This is fun! Try it with a different set of conditions in a different market. Use it to evaluate the startup idea you have - if you’re right, do you destroy your own market or create and own a new one? Is your idea as big of an opportunity as you think, or is it bigger? We’re all guessing what will work when we try to build or invest in something new. There’s no one version that works, but I like having different games and frameworks to think about ideas. Sometimes you just need to think about the founders and sometimes you need to think about markets. And, sometimes, you just need to pretend you’re already living in the future.
I’ll be addressing the topic below along with Alfred Lin from Sequoia and Ilya Sukhar from Matrix on 3/24: https://us06web.zoom.us/webinar/register/WN_qgghYDq4QxCiW9REOOrbmw It would be challenging to name all the fundraising mistakes that founders make during the many demo days that occur each year. There are certainly broad categories, but rather than focus on all of them, I think it’s worthwhile to consider one specific category of error, which is generally one of omission rather than commission: ignoring demo day as a step toward an A. This is a big one because, at least when I ran the data at YC, the best companies in an accelerator tend to be the ones that raise a Series A within 12-18 months of Demo Day (or sometimes a month or two before Demo Day). There’s a strong correlation here driven by the fact that the best companies tend to set and maintain a rapid pace of growth throughout their lives, and that trend leads to rapid milestones. And yet, most founders I talk to treat their Demo Day as a disconnected event. It’s worth thinking about why they do this, what behavior it causes, and how to correct it. On the why: I think it’s fairly simple. Demo Days are stressful and are built and run around the idea that the sole purpose is to raise seed funding. This is true but also misses the point because seed funding isn’t the goal of a company - building a big company is the goal of a company. From that lens, Demo Day and seed funding are part of a larger story, and are tools for executing on a larger vision. Now, many founders will say that they don’t have time to think about their A when putting together a seed, but that’s short sighted. Founders should be thinking about every round they do as it relates to the next round and the next set of milestones the business needs to achieve. You can add to this that most of the advice founders get from various advisors around Demo Day is to close money fast and go “back to work.” But again, this is short sighted. A Demo Day is the only time where many investors are hyper focused on an early stage startup. Squandering that attention is a mistake.[1] Of course founders shouldn’t constantly be actively fundraising, but they sure as hell need to always be thinking about where the money they need to build is going to come from. On top of that, they need to act in a way that increases their chances of raising that money. One more thing - last time I ran the data, it turned out that having a Series A investor in your seed was, on balance, a positive signal for your ability to raise a quality A. I’m sure the numbers have shifted a bit since then, but I’m willing to bet that the conclusion is the same. So, to get to the errors: Don’t ignore Series A investors before or at a Demo day. If you do not plan on raising an “A,” find a way to schedule time with them anyway. Don’t shoehorn Series A investors into the same process that you have for angel/seed investors. They generally work differently, so account for that. Don’t think of your seed round as an isolated event. Think about the amount you raise and the cap you use as a starting condition for your next raise. Limiting dilution is good, on balance, but not if it gives you a cap so high as to impair your ability to raise your next round. Don’t vanish after meeting an investor who seemed interested and who has a good reputation. Figure out how to nurture that relationship and keep the investor interested. Don’t treat investors as interchangeable. It may be true that money is money, but the people deploying it are human and want to build a relationship. You are not trying to make friends, but you are playing a game that is designed to increase the chances of success for your company. Avoiding these errors isn’t necessary or sufficient to raise an A. I’ve seen companies commit nearly every error imaginable and still raise money. However, founders shouldn’t strive to be uniquely lucky in fundraising. Founders should use knowledge about how fundraising works to constantly improve their odds of success. A demo day is an unfair advantage in that process, and founders should treat it that way. __ [1] This goes for the accelerator as well as for the founder. Accelerators should harness the interest of later stage investors vs. designing fully against their interests.
Let’s accept, for the purposes of this essay, that founders and venture capitalists are engaged in a simple trade. Founders sell business risk for the cash they need to take bigger risks; venture capitalists buy that risk hoping it will one day transmute into reward. Each side does this because they believe that, ultimately, the size of the risk is directly correlated to the scale of the potential reward. But there’s acceptable risk and there’s unacceptable risk. No sane person is going to invest in a scheme to turn lead into gold, but early-stage startups—and even some mid- and late-stage startups—rarely present such a clear-cut profile. Investors are often under pressure to evaluate seemingly great ideas and teams without all of the information they’d ideally have to decide whether to put their money on the line. I’ve written in the past about how investors consider the reward side of this process, so let’s focus on the risk side. Some risks are obvious—the market may be too small or the costs too high—not to mention that pesky fact that the future is always ultimately unknowable. But some risks are more idiosyncratic. We call these red flags. There’s been a lot of talk about red flags recently, mostly in the context of FTX and the diligence that its investors may or may not have done before committing their partners’ funds. I happen to believe that investors did a heck of a lot more diligence than they’re being given credit for having done, but I also think that conversation misses the point. Red flags, when you find them, are rarely deal-killers. They’re just pieces of information, indications of risk. The bigger the reward potential, the more red flags an investor should be willing to accept—or even expect. Let’s take a look at a specific type of red flag I’ve seen and the nuances it presents: During the diligence process, an investor discovers that the numbers in a pitch don’t match the numbers on a revenue or income statement. This is, without a doubt, cause for concern. There are two major explanations here—either the founder made a mistake or the founder is lying. If the founder doesn’t seem to understand the numbers, the investor will probably decline the deal—not because of any specter of dishonesty, but rather because the founder is demonstrably incompetent. If the founder gets evasive when confronted, the investor would probably conclude that they’re lying and walk away. But if the founder recognizes the discrepancy as a mistake and quickly corrects it, provided the error is fairly trivial, the investor may lose some confidence but not give up on the deal. There are other classes of red flags. Sometimes the corporate structure is odd (this was true of Facebook, which in its earliest days granted founder Mark Zuckerberg enough super voting shares to ensure his will would go virtually unchallenged), or the company was originally a non-profit (see: OpenAI). Founders get flagged for not thinking deeply enough about a problem and for thinking too deeply about a problem without taking action. Some investors believe that being a first-time founder is a red flag in and of itself, while others see it as a strong positive. Remember: Red flags are very rarely outright fraud, and when they are, it’s often obvious only in hindsight. Different investors have different levels of risk tolerance and generally only agree with each other when someone else makes a catastrophically bad and public mistake. Especially in a later stage company, there are so many places for a malicious actor to hide their dirty dealings that it would be incapacitating for any investor to do all the diligence required to definitively eliminate fraud. Such a thing simply isn’t possible. Look at Enron! Look at Madoff! And finally, on the other side of any red flag is one critical, inescapable question: If the product is selling and the company is making money, how big a problem could it be? What if what looks like a red flag turns out to be a meaningless distraction and the deal you walked away from nets someone else a billion-dollar return? I’m willing to bet that there are investors who passed on Google’s Series A in 1999 because it had almost no revenue—a clear red flag for a company raising $25 million—and are still kicking themselves for it. All of which is to say that so-called red flags matter, but not in any kind of mechanistic way. And if you flip that around, there’s an important lesson here for founders. Every business has flaws that could be considered red flags by someone. (If there are absolutely no red flags, that could be the biggest red flag of all! But I digress…) One of the most useful things a founder can do when preparing to raise capital, therefore, is to take as objective a view as possible of their business and know where those red flags are. For instance, delivery businesses generally have low margins relative to software businesses. Some investors won’t touch delivery for that reason, but most are happy to dig deep provided that margins are improving at a high enough rate that they can turn a hefty profit before the company implodes. One of my favorite misunderstood red flags has to do with the default rate of a lending business. Many founders work hard to demonstrate that their default rate is, effectively, zero. This feels smart, like perfect risk-management. But it is also almost always the wrong answer. Lending requires at least some risk, so if the default rate is zero, it means the founder hasn’t stress tested their model on a broad enough range of users. What investors actually want to see is a reasonable default rate within the context of factors like the cost of capital, the ease of scale, the return profile, etc. As long as the default rate makes sense within the overall story of the business—and that the story ends in huge returns—no red flag. The best thing a founder can do is to draw attention to their red flags proactively and in detail. See this unusual management structure we have? That’s on purpose. See this gap in our revenue over here? We screwed up, here’s how and here’s what we learned from it. In the end, what matters is context—the way whatever red flags there may be fit into the larger narrative of the business. No red flags mean no risk at all, and that wouldn’t be particularly interesting. __ I originally published this in by The Information on Jan 18, 2023: https://www.theinformation.com/articles/red-flags-are-in-the-eye-of-the-beholder
Originally published in The Information on November 2. For the past nine months, nearly every investor with a Twitter account, blog or board seat has been beating a unified and constant refrain: The go-go days are done. Founders were being pushed to build 36 months of runway, whether or not it was actually feasible to cut costs that much. Time and again, investors told me due diligence was back. I watched as fundraising rounds that a year ago would have produced a term sheet in a few days stretched across a full month and dozens of pitches. And then came Dall-E 2’s public release, quickly followed by a flood of wildly cool technology. (edit 12/8: And now ChatGPT!) These events triggered a craze now ripping through venture capital land. We’re seeing billion-dollar valuations for companies peddling products based on generative artificial intelligence algorithms with less than a million dollars of revenue and no proven business model. Not long ago, the same behavior was held up as a cautionary tale about the excesses of VC over Web3 and instant delivery. Now we have a whole new era of exuberance on our hands. The first thing to remember is that this ability to pivot from dark depression to fall-over-yourself excitement is at the core of the startup world’s future-building powers. Seen from another angle, the whiplash looks like optimism, and VC would have vanished decades ago without it. The entire venture model is about funding failure until you find success. There have been times where the entire industry seems to implode, only to come roaring back. I won’t argue that every investor or founder is a walking example of this kind of stoic hopefulness. There are plenty of cynics puffing themselves up by tearing down other people’s ideas (something I—regrettably—did quite a bit of early in my career), and plenty of others who have no particular view on the future other than wanting to make money. The best investors and founders, though, are optimistic realists of the purest sort. This might come across as ignorant or naive, but sooner or later they usually end up being right. Optimism is the key to understanding what’s happening on the frothy edge of the investing world. It would be easy to write off the generative AI craze—after all, there was an AI and machine-learning craze just a few years ago that didn’t lead to much of anything. Add to that the ongoing collapse of several waves of exuberance at once—crypto, fast delivery, public markets in general—and it’s difficult to believe that optimism will actually win out. That said, I see four major reasons why generative AI has venture capitalists acting like it’s Q1 2021 all over again. It’s rooted in an archetypal category of futuristic technology, aka AI. There are any number of plausible paths that end in fat returns. The press has already thoroughly hyped the space as a whole and a handful of companies in particular. Most importantly, there are no public generative AI companies. As a result, there are no visibly crashing multiples or valuations to weigh down private valuations. Coming out of the stock market crash at the beginning of the Covid-19 pandemic, the world did in fact change. Work shifted, shopping habits morphed and the value of venture bets hit astronomic highs. Companies that had been private for a decade decided the time was right for blockbuster initial public offerings, and Wall Street said, “Hell, yes.” That meant big payouts for all the venture investors who’d been patiently waiting for their exit opportunities. As returns surged, new fund sizes surged, and the FOMO cycle kicked in all along the chain. Suddenly it was easy to be optimistic—too easy. Wherever there was software, or even just the idea of software, there was the promise of quick wealth. Then many of the equities that went public to great fanfare quickly fell off a cliff, taking a whole lot of optimists with them. By spring this year, pessimism seemed to have set in. On its face, this was more than a bit baffling. It’s not as if much value has been destroyed—sure, the valuation of, say, Coinbase has dropped more than 80% since its public trading debut, but a market cap of $15 billion is still incredible. Plus, as I’ve already argued, investors are sitting on huge piles of money and they have an obligation to invest. What’s become clear in the last month is that the ancient optimism wasn’t dead, it was merely hibernating. Maybe you could have seen this from the ongoing drumbeat of new fund closes. If you’d talked to the right investors, you’d have discovered that they were still doing deals, just quietly. The market was waiting for a catalyst, and now it has one. It’s important when thinking about how VC works over time to remember that venture investing is driven by narrative more than it is by data. Early-stage companies are valued on their promise, not on what they’ve done. On top of that, an awful lot of venture capitalists devoured science fiction as kids and now, as adults, they fixate on how new technologies can shift humanity. Even if we haven’t yet figured out a positronic brain or proton micropile, AI always tickles that old childhood fascination. Generative AI especially offers tantalizing possibilities. If this new stuff can write marketing copy, is it good enough to topple the world’s largest advertising agencies? It’s possible that image generators will soon remove the need for commercial photography. Maybe we will finally get a conversation engine that makes customer service less awful and renders the call center business obsolete. Each of these is a giant opportunity, and we’ve barely scratched the surface. With the narrative pieces in hand, investors have another hurdle to overcome: peer pressure. Some investors seek out genuinely novel bets, but many want the safety of going with the crowd. Generative AI satisfies both desires, having both whiz-bang appeal and enough press attention to give timid investors cover. It’s all good news for venture capitalists and founders in the generative AI world right now. That won’t last, but right now, it’s easy to argue that the future is bright and golden. Even more, it’s difficult to tie these new companies to the types of public assets that have been hammered of late. Generative AI isn’t software as a service, so SaaS multiples are irrelevant. It isn’t a token, so crypto winter doesn’t matter. For the moment, at least, nothing can spoil the party. All of this is great for the tech ecosystem, including for founders not currently building generative AI companies. That’s not to say companies should start adding random image generators or copywriting features to, say, payment processors. That would be foolish, though I’ve seen worse (not every videogame needs non-fungible tokens!). The lesson for founders is that investors are looking for reasons to be optimistic. Sometimes that means cutting back on hiring or reining in growth plans, but the really savvy founders will find ways to convince investors their companies are the ones that can swim against the current. Let’s all hope generative AI fulfills at least a quarter of the promises people are making in its name. In the meantime, optimism is contagious, which is good for everyone.
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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.”
Scarcity and survival keep you from being your best.
An old playbook is back for the deepfake era. Is it working?
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