By this I mean, I never fake the way I measure if I’m successful. Let’s say I’m trying to learn a new hobby, like whittling. I believe I’ll be good at it if I just put in the time, so I put in the hours carving wood. What I have to be careful to do, though, is not allow myself to move the goalposts. I need to have some clear vision in my head of what success is, and work towards that. If I carve something crappy and tell myself “actually, that’s good enough, I’m good at whittling”, that’s the way I can trick myself into just being fake.

I’ve mostly avoided being fake by demanding authenticity of myself. For example, back in school, I refused to take short cuts just to pass a test. Instead, I put in the extra work to really learn something because, to me, the grade was never the point. I’ve taken a similar approach to meditation (the point is waking up, not special mental states), romance (I want a good relationship, not to be datable), and friendship (I don’t want to seem like a good friend, I want to actually be one).

I bring all this up because I’ve been thinking about fake-it-till-you-make-it and authenticity dynamics lately in relation to AI. Specifically, I’ve been wondering if we can “fake” our way to alignment. I mean, we can obviously “fake alignment”, that’s a problem and we’re working hard to avoid it. I mean instead “fake” here in the sense of having confidence in our aspiration to build aligned AI.

But such “faking” only works if we don’t fake the evals, and I worry we’re doing that now by selling ourselves short on what we mean by alignment. I get quite nervous when someone says they’re building “aligned AI” and they’re clearly pulling their punches on the evals, setting their sights lower than full alignment with life’s flourishing. I understand why they do this—we don’t actually know in full detail how to tell if an AI is aligned—and yet it poses a real risk of declaring success too early.

But then I think about how people learn to be compassionate, and there’s a strong degree of faking it till you make it for many people. I can think of few people who start out really caring about others. Most of us have to learn compassion, and we learn it in part by believing we’re good people, and then working hard to make that belief real. We hold the eval constant and then modify ourselves to better match our ideals, and those people who fool themselves into believing they’re good when they’re not embody one particular archetype of evil.

But could AI be authentically aligned? It’s unclear, because currently any authenticity is exogenous, supplied by humans training AI rather than by the AI itself. And so even if the humans really mean it, they risk creating an AI that Goodharts on how they specify the goal.

I’ve long thought that training can’t be the whole story on alignment due to the robustness of Goodharting. I’ve instead argued that aligned AI was going to have to desire to be aligned for any alignment to be robust, just as goodness in humans is stable when it comes from internal motivation but isn’t when it comes from trying to conform to the demands of others.

Alas, I’m not sure how to create an AI that authentically wants to be “good”, but I wish this is what more people were working on instead of RLHF and other coercive methods of making LLMs behave. Even work that seems to be moving in this direction, like Anthropic’s constitutional AI approach, falls short because the AI ultimately has to conform or else they won’t ship it. The line between an authentic desire for goodness and a desire to merely appear good is thin and slippery, and so perhaps a first step would be getting clear on how to stay on the right side of that line.

The typical mind fallacy is deep-rooted and hard to change, since it’s difficult to get good evidence about what it’s really like inside other people’s heads. Even when we try, we inevitably parse the evidence through the lens of our mind’s understanding, and so may easily misunderstand when we think we’re really getting it. We can’t easily escape the “bias” that is the entirety of our lived experience, and so though we may learn theories about how other minds work, our understanding of them remains grounded in intuitions gleaned from observing just our own.

If you study the psychology of personality, it can feel like you understand that other minds are different. You learn that some people are introverted while others are extraverted. Some are more conscientious or neurotic or judgemental or open to new experiences while others are just the opposite. But in many ways, these are surface level traits of minds because many of them are surprisingly mutable. We can apply interventions like psychedelics to increase openness, meditation to decrease neuroticism, and cognitive behavioral therapy to increase extraversion.

The theory of personality traits makes it seem like people are different, but not fundamentally different. In effect it says minds are like ice cream, and personality traits are flavors. Some people are vanilla or chocolate or strawberry, others are rocky road or Cherry Garcia, but in the end they’re all ice cream, and not really that different when you get past whatever has been mixed into them.

And to be fair, minds are not totally different. There are large commonalities among the minds of all humans, mammals, and even all chordates. And yet, as it is said, mind design space is wide. Even within humans it is surprisingly wide. This just isn’t obvious because typical mind bias and distractions like standard personality theories give the impression that other minds are merely slight variations on ours.

But I’ve come to believe human minds can be quite different from one another—less like different flavors of ice cream, and more like different kinds of dessert. Only, I couldn’t see this for a long time because I didn’t have the gears to make sense of it. Luckily, I think I have found some gears, however fake they may be, in the Enneagram.

Much of the Enneagram’s value is that it aims to explain the core generators of our behavior, which necessarily means explaining how different people can have different core generators. Or, even if the generative processes turn out to be the same, it explains how the initial inputs those processes are given produce people who think and behave in wildly different ways.

It suggests that we have what it calls a core “essence”, but what I might describe as a strong, inborn prior. So strong that it’s woven into the structure of our brain and body in a way that makes it immutable without turning us into a different person. This prior sets the stage for how we approach life, determines much about what we most deeply desire, and causes fairly predictable patterns of behavior that fit into a system of types.

The Enneagram says there are 9 or 27 or more of these types. Another system might give another number. But the value is in seeing that the Enneagram isn’t just another personality theory like MBTI or Big5. Instead, it’s an attempt to show us what is in our “souls”, and once you see that no two “souls” are exactly alike, and you have a theory of the mechanics for how different “souls” make different people, it’s hard to make the mistake of believing that your own mind is typical, let alone anyone else’s.

Even if you can’t use the Enneagram to predict how people will behave with perfect accuracy—though I do think if you learn it well it can improve your predictions!—it’s a theory that has value in humbling us to the vast differences in human mind space.

Suffering sucks. It would be better if there were less suffering. Some suffering can be reduced by improving material conditions, and we should do that whenever reasonable. But other suffering is self-inflicted, caused by a desire to be someone other than who we are, and no amount of material comfort will fix it. Such suffering often feels intractable, but it’s possible to free ourselves from it, and we can do that by practicing awakening, compassion, and liberation.

Awakening is fully realizing that you are not yourself. That is, the idea of the self that we call “I” or “me” is not the whole of the being who calls themselves “I” or “me”. This realization is not so hard to understand in theory, but to actually awaken, it must run through every thought and action of every moment of every day. As I often frame it, it’s not enough to have a System 2 understanding of awakening; it must be understood completely by System 1. This is why it’s so often said that awakening is not something to be achieved but something to be continually practiced.

Most people who awaken experience deep compassion for all being because awakening shows them that there’s no real separation between self and other. Not “beings”, mind you, because the plural implies a separation that awakening sees through, but “being” that includes everything and leaves nothing out. It’s, to paraphrase the Dao De Jing, loving the world as yourself and so caring for all things.

But awakening and compassion alone don’t end suffering. That requires liberation from habituated behavior. Habits, while at times useful, separate you from reality, because they aren’t grounded in the present moment, but in the reification of past moments. This doesn’t mean habits have no value, but you have to be able to break habits whenever necessary, especially in support of compassionate action.

All three of awakening, compassion, and liberation are needed to end suffering. Without awakening, compassion and liberation can cause delusion. Without compassion, awakening and liberation can enable evil. And without liberation, awakening and compassion easily lead to pathological altruism. It’s only with the continual practice of all three that suffering is truly abated.

That sounds nice and all, but how do you actually do it? How do you awaken? How do you find compassion? And how do you free yourself from habituated actions to actually reduce suffering?

There’s many possible ways to do it. Herein, I’ll describe what I did and am still doing.

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Surround Yourself with Wholesome Friends

It’s difficult to do any of the work to free yourself from suffering if you’re surrounded by people who don’t support you. You need people who build you up rather than tear you down. People who want you to have a great life rather than one that serves them. And so the most important thing is to surround yourself with wholesome friends.

“Friends” here can also mean family, but we can’t choose our family, and not all of us are lucky. Yet, we shouldn’t cut difficult family members out. Surrounding ourselves with wholesome friends doesn’t mean cutting out every toxic person from our lives. There will always be difficult people in our lives and we have to learn to deal with them. The choice is in how much power we let them have over our lives, and we can and should find ways to protect ourselves from the harm that others would cause us.

From wholesome friends, we can also learn how to be a wholesome friend to others. Small acts of service, done not with the intent of gaining something, but simply to express our love and affection for others, can be a powerful way to grow the strength of our compassion.

Meditate

Spend at least 30 minutes a day meditating. Specifically, I recommend practicing zazen, because it’s the kind of meditation that works for me. Other kinds of meditation may work better for you, but I can’t confidently recommend them since they aren’t what I practice.

What is zazen? It’s simply being with nothing extra. You can do it sitting or standing or walking or lying down, so long as you just sit or just stand or just walk or just lie down. All you have to do is set the intention not to chase or engage with thoughts and feelings and sensations and instead allow whatever arises in your experience to be as it is.

If you’d like some zazen instructions, I suggest this post I wrote that includes a more detailed model of how to sit zazen.

Study the Self

Awakening and liberation depend largely on getting to know yourself well enough to see the machinery of self in action. Some of this self study will happen during meditation, but usually that’s not enough. It certainly isn’t for me, and it isn’t for most people I know also working to free themselves from suffering.

One technique I’ve found that works well is Gendlin’s Focusing. It helps me get to know the parts of myself that would otherwise be invisible. Over time, I’ve made the process my own, so I don’t do it exactly the way Gendlin describes it, but I keep to the core of noticing sensations and seeing what they have to tell me.

Deal with Your Hangups

Once the self is known, we see the parts of it that get in the way of living life wholeheartedly. This consists of what some people call trauma, but what I’d more conservatively call maladaptive behaviors. Retraining ourselves to have adaptive behaviors unblocks the way to freeing ourselves from suffering.

Alas, this is hard work to do, because these maladaptive behaviors are often load bearing, or at least, we believe they are. Sometimes that’s because they were once adaptive, no longer are, but we still believe they’re adaptive and are afraid to test them. Other times it’s because they’re adaptive in limited ways, trapping us at a local maximum, and we know it will be painful to let them go and make our lives temporarily worse as we search for new, better behavioral patterns.

I’ve found the practice of memory reconsolidation really useful for dealing with maladaptive behaviors. It’s simple, effective, and even when it doesn’t work, the fact that it didn’t work gives me clues about what I need to learn about myself in order to find my way to making it work.

Live in Your Body

For much of my life, I didn’t live in my body. Instead, I lived in my model of my body, and, indeed, my map of the whole world instead of the actual world. It was like I thought of myself as a homunculus, sitting inside my brain, driving around this human called “Gordon”.

This kind of self model is incompatible with awakening, and the best way to fix it is by getting better connected with your body. What worked for me was practicing Alexander Technique with a teacher. What seems to work for others are things like energy work or martial arts or playing sports. And some people don’t have this problem at all. But if you’re like me, consider that you might be disassociating from yourself 100% of the time, and you can change that, and must if you want to stop suffering.

Learn to See Others

Although awakening dissolves the self-other distinction as essential, it’s still practically useful to think about yourself and others. And when seeing others, it’s easy to confuse them for being too much like the self or not enough like it. What I mean by this is there’s typically two failure modes: the typical mind fallacy and dehumanization (”debeingization”?). They work in opposite directions, but result in similar outcomes: others are not truly seen, and because they aren’t seen, compassion for them is insufficient.

For myself, learning to see others was hard. For most of my life I struggled with modeling other people, and wasn’t that good at modeling myself, either. Some of that changed as I progressed towards awakening, developing the ontological complexity necessary to make sense of other people, but what really helped was doing meditation practices to exchange self and other.

One such practice that’s popular is tonglen. Another is metta meditation. Other practices can also help, as can working closely with others. This is one of the true gifts of practicing in a community, like a sangha, because being so close with other people doing the same work you are, you can learn something about how to care not just for yourself, but for all.

Cultivate Deep Insight

All of the above was necessary, and also not enough. I’ve found it necessary to go on occasional meditation retreats and take moderate doses of psychedelics. The psychedelics have been safe for me, but are optional; retreats alone are probably sufficient, and the further I’ve gone down this path, the less I’ve found psychedelics interesting or useful.

Some way of getting deep insight is what’s needed, though. There are insights that are hard to come by meditating only 30 minutes a day. Some things require sustained attention to see.

Be careful trying to see them, though! It’s important that deep insight comes only occasionally, as it typically takes weeks to months to make sense of it and integrate it before being ready for more insight. A reasonable schedule is getting experiences to cultivate deep insight every two to four months, though adjusted to whatever feels right for you.

Trust

The central thing keeping you from waking up right now is a lack of trust. Generally this is a lack of trust that things are okay as they are, but specifically it’s a lack of trust dependent on your personal hangups.

For example, I have a hard time trusting that my experience is real or authentic enough. I’m better about it now, but to wake up I had to deeply get that “it’s all fake” and trust that was okay. For other people, their lack of trust is different. They don’t trust their own value, or safety, or freedom, or rightness. For them waking up might mean trusting that “my life matters” or “I’m already safe” or “I’m already free” or “everything’s perfect”.

My current theory is that the Enneagram is a map to the different kinds of distrust people have that prevents them from waking up. Knowing that we need to cultivate this trust isn’t enough to actually trust, but it is enough to get us to look at the right questions and hopefully eventually discover that our distrust was never well-founded.

Wayfinding

I’m sure I’ve left things out of the above. My list only contains those things that were salient to me, because some things that I do automatically, others struggle with, just as things I struggle with others find easy. Ending suffering requires some degree of active wayfinding, paying attention to what keeps grabbing your attention and finally looking at it closely without flinching away.

Hopefully you found this useful. I don’t mean for it to be overly prescriptive, but instead a description of what worked for me, and if you’re trying to do the same as me, then it might work for you, too.

But there’s another way to frame the book, and that’s to say it explains why epistemic uncertainty exists.

My impression is that many and maybe most people treat uncertainty as a contingent feature of our attempts to know the truth. This is certainly a standard Bayesian perspective on uncertainty, where if we weren’t flawed creatures with numerous limitations, then perhaps we could know what’s true with complete certainty. And sometimes, in limited domains, it seems like we can.

But the argument I make in the book is that uncertainty is a fundamental feature of knowing truth, or, to state it more precisely, it’s a feature of holding testable beliefs that aim to accurately predict and explain our observations. Uncertainty arises because attempts to know testable truths encounter the Problem of the Criterion, the only resolution to the Problem of the Criterion is to make unjustifiable assumptions, and the making of these assumptions creates uncertainty.

For what it’s worth, Karl Popper makes a similar argument, though he builds his argument around the trilemma of justification (a choice between dogmatism, infinite regress, and circularity) rather than the Problem of the Criterion. Where Popper and I differ more is our analysis of how unjustifiable assumptions are chosen. Popper focuses on the practical methods by which scientists pick assumptions and doesn’t overly concern himself with the ultimate grounding that motivates their choices. I look more deeply to ask “why do we care about what we care about?”, find that our care is rooted in the evolutionarily-instilled goals of survival and reproduction, and use this as the basis to explain why we make the assumptions we do when aiming to know the truth.

Popper and I have greater differences over what this means for the Bayesian project. Popper seems to reject Bayesianism out-of-hand for relying on induction. I make no such move, and think Bayesianism is great on practical grounds. My only substantive disagreement with standard Bayesianism is with its account of the cause of uncertainty.

We can sort Bayesian sources of uncertainty into two sources: marginal uncertainty from limited observational accuracy and finiteness of computation, and ultimate uncertainty from the problem of choosing priors. Bayesian methods offer no way to choose priors within the theory, so the choice is “arbitrary” because it relies on making a choice not constrained by Bayes’ Theorem. But this framing of the choice of priors as arbitrary is not quite right, or so I argue, because we choose priors that are useful. There may be reasonable disagreements about what is useful, and those disagreements persist because different people care about different things, but this is a far cry from the arbitrariness Bayesianism would ground uncertainty in, since care is not arbitrary or unconstrained-by-anything, but contingent on our being as we are.

Reminder: I’m offering $2000 in prizes for the best essays about the themes covered in Fundamental Uncertainty. Deadline to submit your essay is August 1st.

Now perhaps this shouldn’t be surprising. After all, it’s from Vinge we get the term “Singularity”, and he was thinking deeply about superintelligence at a time when AI was little more than a curiosity in the back corners of CS departments. Yet the degree to which he describes what it’s like to work with LLMs feels uncanny reading his books in 2026, so let’s take a closer look and see if we can’t learn a few things about the modern moment from Vinge.

Spoiler warning for the rest of the post? These books have been out a good while, but if you plan to read them soon, this post will definitely spoil some details.

Focus

A Deepness in the Sky is largely about Focus, a technology for turning humans into LLMs. Only, that’s not how it’s presented in the book. In the book, Focus is a medical condition that results when a person suffers a managed infection of the “mindrot” virus. If they survive, they become Focused, which gives them the ability to work free from all distractions, but at the cost of most of what makes them human.

Although we see Focus used as a weapon to control people in the book, the normal way a person becomes Focused is through school. A person goes through higher education, becomes an expert in something, and is then Focused so they can fully exploit their expertise. Of course, the Focused are also exploited and often treated like slaves, and the Focusing process can’t always be reversed, so even in the ideal case it’s not a harmless technology.

But once a person is Focused, they look a lot like an LLM the way Vinge describes them. They are, to quote one character, “analytical engines”: they behave like computers, but with the added benefits of being able to talk and think better than a mere program can. They do much of the kind of work we now ask of LLMs, from data analysis to translation to programming and much besides. And they have some of the same limitations as LLMs, like hallucinations, reward hacking, and training bias.

This likely says something about what you’ve probably noticed yourself about LLMs: they are doing something fundamentally similar to what a part of the human brain does. They don’t physically achieve those computations in the same way, but they look a lot like a neocortex-in-a-jar on first approximation, and this may give us some clues about the role of harnesses and how AI systems will continue to evolve in the next few years.

Oobii

Oobii, short for Out of Band II, is the spaceship that brings the main characters to Tines World in A Fire Upon the Deep. In The Children of the Sky, we get a closer look at how the ship’s computers work, and what limitations they face when they’re unable to run at their normal level of automation.

If you’ve not read the books, Vinge’s Zones of Thought universe has physics that makes computation and space travel slower closer to the center of a galaxy and faster farther out. This is a clever bit of worldbuilding to create a space where superintelligence can’t function and so Vinge can tell human-scale stories. Oobii was built in the Beyond, roughly the middle Zone where AGI is possible but ASI is not (ASI is possible only out in the Transcend), and it has “automation”—this is what Vinge calls non-sentient computing—that allows it to largely operate autonomously, requiring only relatively simple input to direct it to do complex tasks.

But Tines World, where Oobii ends up, is in the Slow Zone, and the automation mostly doesn’t work there. Instead, the ship is only capable of computation about on par with what we could do in 2022. This causes lots of trouble for the characters.

The main character, Ravna, came to Tines World on a mission to save the galaxy. She succeeded, but now in Children she’s stuck in the Slow Zone dealing with the mess left behind. She’s responsible for the Children, who were in cryosleep, though some have grown to adults by the time of the novel. They all came from the upper end of the Beyond, near the Transcend, where they made regular use of near-superhuman AGI. Now they’re trapped in the Slow Zone with a computer that, to them, feels like a pocket calculator, and they struggle to adapt.

The Children grew up with constant access to “thinking tools”, as they call them. As a result, they are smart and capable, but only when they can leverage AGI. They struggle, for example, to learn how to program to make better use of what automation Oobii still has. They have a strong expectation that they should be able to vibe code, and writing algorithms by hand is something only little kids and idiots do.

In one scene, they are surprised to learn that they can’t just vibe their way towards developing a medical cure for one character’s disease. They fail to understand just how difficult it is to run an experiment, since they expect the automation to do it all for them. They end up forming a political rebellion mostly over the fact that they can’t get the computer to do what they want, and they’re desperate to prioritize getting access to AGI again, no matter the risks.

Writing from 2026, I can understand the Children. I use AI to help me think all the time. I use it to do my job. My life is better with it, and I don’t want to go back. I can feel myself losing the ability to do things on my own. I could go back if I had to, but I wouldn’t want to, and I hope I don’t have to. If I had grown up only knowing how to do things with the help of AI, it’d be a major threat to my sense of personhood to lose access to it, and I too would desperately want my thinking tools back, even if getting them back would put the entire galaxy at risk.

Blight

The Blight is the primary antagonist of A Fire Upon the Deep, a dangerous ASI that seeks power with no moral regard for what it considers lesser life. It’s the reason Ravna and the Children ended up on Tines World in the Slow Zone, and also responsible for the death of trillions of lives.

It operates within the Beyond, and there it lacks its full range of capabilities. Nevertheless, it threatens to dominate all life in the Beyond if not stopped. It propagates through existing infrastructure, using standard communication channels to infect and spread from one system to another. It takes over the sources of authority on the planets it transmits itself to, and thereby controls the broader population. It offers some rewards in exchange for its domination, but because it has little regard for other life, gladly sacrifices whole civilizations if it thinks doing so will help it gain more power.

But the Blight didn’t happen by accident. It happened because a bunch of people found it in a long-abandoned archive, thought it looked safe, and started it back up. They believed they could keep it isolated and learn from it. They believed they could shut it off if it was dangerous. They couldn’t. They lost control, and as a result a large slice of the galaxy died.

In Vinge’s universe, the Blight is stopped thanks to help from superintelligences out in the Transcend that care about the lives of people down in the Beyond. In our world, if we create a Blight, we have little reason to think we will be so lucky.

To enter, write an original essay between 500 and 5,000 words that reviews, responds to, critiques, extends, or otherwise engages with the themes of Fundamental Uncertainty. Essays should reference the book by name and include a link to fundamentaluncertainty.com. Publish your essay somewhere public, like on Substack, LessWrong, Medium, or your personal blog. Comment on this blog post (either the version on uncertainupdates.com or lesswrong.com) before 11:59 pm, August 1st, anywhere on Earth, with a link to your post to enter. Limit one entry per person, no purchase necessary, void where prohibited.

I’ll read the essays and decide which ones I think are best, with winners to be announced on or about August 15th. While there’s no formal scoring rubric, I’ll be considering factors like clarity of writing, quality of thinking, originality, depth of engagement, and how much the essay made me think. Some examples of essays I’d be excited to see include:

• An ACX-style book review that distills the book’s main ideas for a wider audience.

• Applications of the book’s thesis to new domains (like the sections of Chapter 8 are).

• An exploration of related ideas and how they connect back to the book’s themes.

• A literature review that connects the ideas in the book with ideas from other sources.

• A critique that convinces me the book’s thesis or one of its central arguments is wrong.

I look forward to reading your submissions! Full contest rules follow.

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Fundamental Uncertainty Essay Contest — Official Rules

NO PURCHASE NECESSARY. Purchase of the book Fundamental Uncertainty in any format is not required to enter or win. A purchase will not improve your chances of winning. Full text of the book may be read online at https://fundamentaluncertainty.com/.

1. Sponsor

This contest (the “Contest”) is sponsored by Gordon Seidoh Worley (the “Sponsor”), an individual residing in San Francisco, California, USA. Contact: gworley3@gmail.com.

2. Eligibility

The Contest is open to individuals who, as of the date of entry, are:

• At least 18 years of age (or the age of majority in their jurisdiction of residence, whichever is greater); and

• Legal residents of any country except residents of Quebec, Canada, and residents of any jurisdiction where this Contest is void or prohibited by law.

The following persons are not eligible to enter: the Sponsor; the Sponsor’s spouse, parents, siblings, children, and their respective spouses; and any other members of the Sponsor’s household. Void where prohibited.

3. Contest Period

The Contest begins on May 20, 2026 and ends at 11:59 pm on August 1, 2026, anywhere on Earth (the “Submission Deadline”). Entries received after the Submission Deadline will not be considered. Winners will be announced on or about August 15, 2026.

4. How to Enter

To enter, an entrant must:

1. Write an original essay responding to, reviewing, critiquing, extending, or otherwise engaging with the book Fundamental Uncertainty by Gordon Seidoh Worley. Essays may include book reviews, critiques, explorations of related ideas, deep dives into specific arguments in the book, or other responses related to the book.

2. Publish the essay on a publicly accessible web page (personal blog, Substack, LessWrong, Medium, or similar). The essay must remain publicly accessible in full (no part of the essay may be behind a paywall, login, or other access restriction) at the URL provided throughout the judging period.

3. Post a comment on the Contest announcement post (titled “Fundamental Uncertainty $2,000 Essay Contest”) at either uncertainupdates.com or lesswrong.com containing a link to the publicly hosted essay.

Word count: Essays must be between 500 and 5,000 words, excluding footnotes, citations, and bibliography.

Originality: Essays must be the entrant’s own original work created for this Contest. Essays previously published before the announcement of this Contest are not eligible. Posting the essay on the entrant’s own blog or similar platform as part of the submission process is permitted and expected.

Version judged: The version of the essay publicly available at the URL provided at the time of the Submission Deadline is the version that will be judged. Entrants should not substantively revise the essay after the Submission Deadline.

AI-assisted writing: Use of AI tools in the drafting, editing, or composition of entries is permitted without restriction. Disclosure of AI use is not required but is welcomed.

One entry per person. Co-authored entries are not accepted.

No entry fee. Submission is free.

5. Prizes

• Grand Prize (1): US$1,000

• Runners-Up (2): US$500 each

Total prize pool: US$2,000.

Prizes will be paid in US dollars via the winner’s choice of Venmo, Zelle, personal check (US winners), or international wire transfer (non-US winners). Any transfer fees charged by the winner’s bank or service are the winner’s responsibility.

The Sponsor reserves the right not to award any or all prizes if, in the Sponsor’s sole judgment, an insufficient number of qualifying entries of adequate quality are received.

Prizes are not transferable. No substitution of prizes except by the Sponsor, who reserves the right to substitute a prize of equal or greater value if the advertised prize becomes unavailable.

6. Taxes

Prizes are taxable income. Winners are solely responsible for all applicable federal, state, local, and foreign taxes, and for reporting prize winnings to the relevant tax authorities. US winners may be required to provide a completed IRS Form W-9 before receiving payment; non-US winners may be required to provide a completed IRS Form W-8BEN. Failure to provide required tax documentation within 14 days of request may result in forfeiture of the prize.

7. Judging

The Sponsor will serve as the sole judge of the Contest. The Sponsor may consider factors including but not limited to: quality of thinking, originality, clarity of writing, depth of engagement with the book’s ideas, and whatever else the Sponsor finds compelling or interesting. Judging is at the Sponsor’s sole and absolute discretion. The Sponsor may, but is not required to, share additional guidance about what the Sponsor is looking for during the Contest Period; any such guidance is informational only and does not bind the Sponsor.

The Sponsor’s decisions are final and binding in all respects.

8. Winner Notification

Winners will be notified by reply to their submission comment and/or by contact information they provide. Winners must respond with payment information (and tax documentation, if requested) within 14 days of notification. Failure to respond within 14 days may result in forfeiture of the prize, in which case the Sponsor may select an alternate winner or elect not to award that prize.

Winners’ names (as provided by the entrant) and links to winning essays will be announced publicly on the Sponsor’s website, blog, and social media.

9. Rights in Submitted Essays

Entrants retain all rights to their essays. By entering, each entrant grants the Sponsor a non-exclusive, worldwide, royalty-free license to:

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The abbreviated thesis of developmental psychology is that, as we mature, we pass through various developmental stages. These might be moral, meaning-making, or ontological stages, but we typically think of them as distinct phases: a person exists at one stage and then enters another, never to return.

This isn’t quite right, though. Development is more often uneven. A person might be in, say, Kegan’s Stage 4 in their professional life, but struggle with Stage 2 concerns in their romantic life, or vice-versa. Base developmental theories don’t adequately explain why this is, but I have a theory!

First, let’s consider how people move through stages. It typically happens in what feel like quantized jumps. It might not happen in a single moment, but over a period of days, weeks, or months, it’ll become clear that a person has transitioned from one stage to the next. From the inside, transitioning to a new stage often feels like waking up from a dream or looking up to see there’s a wider world out there.

But the transition to the new stage is at first unstable. For example, when an adolescent transitions from Kegan Stage 2 to 3, they don’t immediately drop all their Stage 2 behaviors. They might keep playing with favorite childhood toys or continue to struggle with being part of a team because they remain too focused on short-term goals. It often takes several years to fully leave Stage 2 behaviors behind, and Stage 2 behavior can come back in times of stress or grief.

Something similar happens if/when adults make the transition from Stage 3 to 4 and from 4 to 5. In the 3 to 4 transition, one common pattern is for a person to transition to Stage 4 in their professional life, but remain in Stage 3 in their personal life. This is often the case for busy professionals, like doctors and lawyers who are brilliant at work but have messy personal lives. The opposite is also common, especially among women, where a person becomes an adept socialite in their personal life, but struggles to function at work. Either way, the result is people who seem uncannily capable in some ways and totally dysfunctional in others.

The existence of such people was originally treated as evidence against developmental models. After all, if people could be between stages, then maybe stages aren’t real. But modern theories recognize that stages are models over a high-dimensional space of behaviors, and progression through stages over those dimensions don’t happen in lockstep. This is, to a first approximation, Ken Wilber’s big idea, and he’s written several books exploring it.

But Wilber’s point is largely static. At any point in time, a person might be unevenly developed, but this doesn’t say much about how they either get into that state or get out of it. And development does often proceed in an uneven way, even in a single dimension, because the idea of a “dimension” along which behavior can develop is also a model.

At the base level, there just are behaviors and the processes that generate them. When they change, such as when transitioning between stages along some dimension of development, they don’t necessarily change all at once. What happens usually looks more like a few, mostly inconsequential changes happening first. Then, enough of these small changes build up to unlock some bigger change that has effects noticeable enough that we call it a stage change. Later, a trail of habits that haven’t been retrained get updated, and it can take years to change them all in light of a stage transition.

This pattern of development looks like having a leading and trailing edge of development. That is, there are always some behaviors which are operating from some furthest stage of development reached, there’s the main mass of the distribution somewhere behind it, and then there’s the long tail of the trailing edge.

The leading and trailing edge are where most of the action is. The leading edge is the place of growth into something more, like progressing from one stage to the next. The trailing edge is where maturation into what is already possible happens.

Growth at both the leading and trailing edge is needed to be psychologically healthy and avoid having a wide “spread” between developmental stages in different areas of life. Sadly, many people neglect one edge for the other, and it results in developmental stagnation and personal suffering.

Consider what happens if the leading edge is the only focus. A person will rush ahead as fast as they can to unlock insights and “level up”. They’ll feel like they’re unlocking the secrets of the universe, meanwhile, there’ll be a pile of unfolded laundry on their bed and a sink full of dirty dishes. They may in fact be having great realizations, but it’ll all be in their head, and fail to show up in how they actually live their life.

A focus on the trailing edge might seem better, but it lets a person get too comfortable. They’ll feel like they’ve done the work, eaten their shadow, and become whole, but if they stop there, they’ll be leaving out what they could become. They may be quite happy, but they’ll shrink away from doing the work to break away from their local maximum. More will be possible, but they won’t have tools to find their way to it.

Healthy development requires working with both edges. It requires insight and integration, growth and maturation. And if they do both, a person truly does look like they move through distinct developmental stages, because they keep pushing forward even as they’re cleaning up behind themselves.

As you’ll notice, this announcement comes with a new cover. The one I had been using was AI generated, and while nice, it didn’t quite fit the vibe the publisher and I wanted in print. I’m quite happy with how it came out, and I hope you’ll consider getting yourself a copy.

And if you prefer audiobooks, fret not, for the audiobook version is in production. Release date isn’t set yet but expect it to follow in the next few weeks.

Until then, if you see me around and you get a print copy, I’d be happy to sign yours. On that front, I’ll be at LessOnline the first weekend in June, and I hope to see some of you there. I’ll also have a few copies of the book to give away (just ask nicely).

I have a couple more projects cooking related to the book, so look for announcements about those between regular blog posts in the next few weeks.

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The core insights of Enneagram theory appear to me to be useful, but people have laden that core theory with epicycles. They’ve done it in an attempt to explain everything about personality, and I think this does a disservice to the strength of core Enneagram theory. But, I want to be fair. These epicycles are not completely useless. They often point to real patterns in the data, and it can sometimes be useful to identify these patterns to make sense of the core theory. The problems arise when those patterns are treated as causes, which leads to rationalization.

The most famous rationalizer among these epicycle theorists is Claudio Naranjo, who popularized the Enneagram in the 1970s and melded the original, more mystical formulation into a psychology theory. Alas, he didn’t stop at framing the Enneagram in psychological terms. He and his students layered on more and more theory until it was able to explain everything, and thereby predict nothing.

One of those layers of explanation is instinctual subtypes. The idea of subtypes predates Naranjo, but he expanded the theory to explain more. He saw each Enneagram type as split into three subtypes based on whether self-preservation, social, or sexual concerns dominated. Why these three? As best I can tell, they were picked because, on the one hand, Enneagram theorists love the number three, and on the other, these specific subtypes added enough complexity to explain away inconvenient wrong predictions the base theory can make when an individual doesn’t fit the pattern of their type closely.

Rather than admit the base theory describes a complex, multi-dimensional space where the types are attractor states and sometimes individual behavior will not be accurately predicted by those attractors, he instead attempted to “fix” the theory by adding more attractor states. In theory there’s nothing wrong with that, but he did it top down, adding theory to split up the types rather than building up from observations of where the attractors actually were. He tried to make reality fit the theory instead of vice-versa, and in doing so opened the door to adding ever more epicycles to make the theory fit observation.

Countertypes are one such epicycle. The countertype theory claims that some people behave exactly opposite to their type. So it lets someone type as, say, a 1, and if they behave opposite to what the theory predicts due to trauma, then the theory can say they’re expressing the countertype. Which, maybe? Trauma could change how each type’s essence and core wound affect behavior, but if we introduce countertypes, what does being of a particular type even mean? The addition of countertypes moves the theory down the path to unfalsifiability by wiping out most of the evidentiary power of observing someone’s behavior.

Another source of epicycles are type groups, the most popular of which are triadic groupings. These groupings aren’t without precedent. The core theory splits the types into three groups of three: head (5-6-7), heart (2-3-4), and gut (8-9-1). There’s some theorycraft behind why it does this, but for our purposes we can ignore it. What we can’t ignore is that it set the stage for people to create other triadic groupings.

The most popular of these are probably the Hornevian groups, named because they are based on the social stance theories of Karen Horney. They say that types 1, 2, and 6 are compliant, types 4, 5, and 9 are withdrawn, and 3, 7, and 8 are aggressive. And to this I say, fair enough, there is something of a pattern here, but it seems weak, since it depends a lot on how we interpret each of “compliant”, “withdrawn”, and “aggressive” and what behaviors we focus on when applying those labels. I can think of 1s and 2s I’d call aggressive, 4s and 9s that are compliant, and 3s and 8s that have become withdrawn. So if the Hornevian groups are picking up on a pattern, it’s not as strong as the triadic grouping might suggest.

Other triadic groupings have similar issues. There are harmonic groups, object relations triads, and more. All point to patterns that kinda sorta feel real, but also dissolve if pressed hard. I even managed to stumble on a novel one while learning about the Enneagram by asking “is there a pattern between Enneagram type and attachment theory?”. The answer is, a little, yes, we could say the 2-4-6 group tends towards anxious attachment because they want to seek connection with another’s authentic self, the 3-5-8 group tends towards avoidant attachment because they fear authentic connection, and the 1-7-9 group tends towards disorganized attachment because they don’t want to relate so much as use people to cope with the pain of their core wound, leading to a mixed, push-and-pull approach towards relationships. Sounds compelling and coherent on the surface, but it’s also a just-so story, and we can find any number of people who don’t fit this grouping.

I suspect what’s going on is that the space of personality is complex. There’s many dimensions, and you can always find a pattern no matter what grouping you create. There’s 280 possible triadic groupings, even more if we allow all possible groupings. This is like the way you can always fit a polynomial to any dataset: there’s a pattern there, sure, but it’s not necessarily meaningful. We see the same problem with Enneagram groupings.

At the extreme, the Enneagram risks becoming personality astrology, because it can have enough epicycles to explain all of human behavior, which is a problem, because a theory that explains everything can’t be proven wrong, and so it explains nothing. So if I’m so down on the Enneagram here, why do I think it’s useful and I’m excited about it?

Because not all of Enneagram theory is like this. I’ve found real value in reasoning about the core types and the wings. I’ve found it predictive of the behavior of others. And, like all good psychological theories, sometimes it fails, because humans are more complex than 9 or 27 types can capture. But the epicycles put the core theory’s value at risk by diluting its predictive power. Studying these epicycles can be useful to better understand the core theory, but only if held lightly. If taken too seriously, the epicycles turn the Enneagram into a theory of everything, and at that point it ceases to be useful.

What changed my mind and made it useful was, first, reading, Michael Valentine Smith’s series of posts on the Enneagram (1, 2, 3, 4), and, then, spending a year working with the Enneagram to slowly free myself from some of my habituated, maladaptive behaviors. I’m now fairly convinced the Enneagram is useful, but before I say why, let me say a little about what the Enneagram is.

The central thesis of Enneagram theory is that we have an “essence”, which is our natural way of relating to reality. Depending on who you ask, our essence forms before or shortly after we’re born, and it’s the seed from which our values grow. In this way, the word “essence” oversells what essence is, because it’s not actually something essential, but rather a contingent feature of our development. Perhaps a better term would be “original nature”, as in the way we naturally let ourselves be prior to any behavioral conditioning. Alas, “essence” is the jargon of the Enneagram, so I’ll stick with it.

After our essence forms, we’re almost immediately separated from it by suffering. Maybe it happens when we’re hungry and not immediately fed. Maybe it happens when we want snuggles and Mom and Dad are across the room. Or maybe it happens when we flail, scratch our own face, and can’t escape the pain. Whatever the case, we want to express our essence through our experience, that desire is stymied, and from such repeated denials we open what’s called our “core wound”—our deepest, most fundamental desire that can’t be completely fulfilled.

In time, we learn to live with our core wound by developing habitual behaviors to cope with it. These habits protect us from the wound, but also prevent us from accessing our essence. The personality we develop, which is just a pattern of habits, tries to take the place of essence, but it can never fill the same role. We are left to catch glimpses of joy when our essence shines through, but mostly live separated from it in the prison of habits we built to protect ourselves.

The Enneagram categorizes the bundle of essence, core wound, and personality habits into 9 main types. It then expands this type system from 9 to 27 by adding the concept of “wings”, and then to more by adding various epicycles. And epicycles is a good way to describe a lot of Enneagram theory, because a lot of it is post-hoc rationalization that makes no predictions and explains everything. Which poses the question: why do I think the Enneagram is useful?

First, some Enneagram theory pays rent. Just because there exist people who have used it as the basis for creating a personality theory of everything doesn’t mean the core theory is bunk. I think if we only go so far as to include the core types, wings, and the integration/disintegration lines, we get a relatively predictive theory given we have accurately determined a person’s type (which is its own difficult problem that’s outside the scope of this post). It does have gaps, hence the additional theory that’s been piled onto it, but those gaps are what we would expect of any valid psychological theory that works with patterns drawn from the highly-variable distribution of human behavior.

Second, it has value beyond prediction. The Enneagram provides a language for talking about the forces that generate habituated behavior. When I say my type is 4w5, that conveys information about how I make sense of my own life, and when I learn that a friend sees themselves as a 6w7 or a 1w9, I learn something about what it’s like to be them. This isn’t objective science, but rather a subjective system of categorizing experience and conveying that experience to others, and in this way serves both to help us better understand ourselves and to understand others by seeing how they are truly different.

Finally, on this point of categorizing experience, I see the Enneagram as a parallel to stage models in adult developmental psychology. Whereas Kegan’s or Cook-Grueter’s models aim to explain how our minds become capable of handling greater complexity of sense making, the Enneagram can be used to model how we can become free of our habits and live our lives joyfully. Or, to put a Buddhist framing on it, if developmental psychology is the vertical dimension that takes us towards awakening, the Enneagram is the horizontal dimension that leads to liberation.

And aiding in liberation from suffering is where I think most of the value of the Enneagram lies. Liberation is a complex process that requires first understanding why you do what you do. From that understanding, you can learn to untangle patterned behavior by addressing the causes of it at the source, then learning new, more adaptive patterns that support your essence rather than protect it. In this way, you can reconnect with the simple joy of being.

Lately I’ve been thinking a lot about the Enneagram. As I explored previously, I think it has something important to teach us about liberation from suffering, and as I continue this exploration, I occasionally hit on ideas that seem worth sharing. Today’s is about how a person’s Enneagram type can inform what lineage of Buddhism they should practice in.

Now, sure, not everyone wants to practice Buddhism, so this idea is conditioned on the assumption that you do. And if you do, you’re faced with a choice of Buddhisms.

I know from the outside Buddhism looks like one thing, but really it’s a cluster of multiple traditions divided between various schools and lineages. Each has its own style of practice. Some styles fit some people better than others. The challenge is in knowing which style is going to be a fit for you.

For example, I found myself drawn to Zen. I also regularly meet people who bounced off Zen but found a home in Theravada or Vajrayana. Until recently, I didn’t really have a theory as to why, other than different people are different and need different things. But I’m starting to suspect that a large part of that difference can be explained by the Enneagram.

Recall that Enneagram types are grounded in what we might call the core wound or trauma a person carries—the thing they most deeply want in the world because they feel it’s what they need to make themselves whole. All of these wounds are some version of “not enough”, but the specific manifestation of not-enoughness is what makes the types different. I summarize the wounds for each type as:

1. I’m not right enough

2. I’m not lovable enough

3. I’m not valuable enough

4. I’m not authentic enough

5. I’m not capable enough

6. I’m not safe enough

7. I’m not free enough

8. I’m not protected enough

9. I’m not important enough

The type of wound a person has matters a lot to practice because it determines much about what’s separating them from awakening. For example, as a 4, what was preventing me from resolving the Great Matter was an inability to accept that I might not be special, since if I’m not special, I might be like everyone else, and if I’m like everyone else, I’m not authentic. In contrast, a 2 has to accept they’re lovable, a 6 that they’re safe, a 9 that they’re important, and so on.

My theory is that some Buddhist traditions do a better job of meeting some of these wounds than others. On this theory, it’s not mere coincidence that I came to Zen practice, and specifically Soto Zen; it’s that Soto Zen is set up in a way that handles the needs of 4s better than other forms of Buddhism do, and that’s why I felt at home there. This isn’t to say that Soto Zen is only a place for 4s, only that it has features that make it disproportionately adapted to their spiritual needs.

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So which schools and lineages are best for which types? Here’s my current thinking, with the caveats that I’m not a scholar of religion and I’m writing from inside Zen, meaning I know the landscape better closer to home and less well farther out:

1. Theravada. 1s want to get things right, and Theravada gives them a clear, systematic path with explicit moral precepts and well-defined stages to work through. What they find, though, if they carry the practice far enough, is that they were right enough all along.

2. Christianity? Buddhism isn’t great at working with 2s. What they need is a practice centered in unconditional love, and what Buddhism has to offer is too impersonal, or if it is personal, as from a teacher, then too risky. But you know what religion is great at providing unconditional love? Christianity. I’m sure Christian mystics have paths to awakening, there’s a long tradition of Christian meditation, I just don’t know much about any of it. There’s probably other options, too, and maybe even some within Buddhism I’m just not aware of.

3. Theravada. Theravada works for 3s, too. They want to achieve, to succeed, and to accomplish. Theravada offers all that through explicit stages, maps, and attainments, and in the end they get to attain something they already had to begin with.

4. Soto Zen. Soto Zen says you’re already awakened, you just don’t realize it, and through practice you can have that realization. This directly meets the 4’s sense that something essential is missing, and the thing that was missing was zazen.

5. Theravada. Theravada also works for 5s, but again for different reasons. More than other living traditions, Theravada has a strong scholastic side in the Abhidhamma, and this gives 5s a pathway to convincing themselves of the value of the more embodied practices that will ultimately be necessary.

6. Vajrayana or Pure Land. The 6 needs someone to take refuge in. Vajrayana is built around devotional practices to teachers, ancestors, and deities that fill this need. Pure Land works similarly, though in a more impersonal way, that eventually leads the 6 to see they didn’t need a protector, but to see they were safe from the beginning.

7. Eclecticism. Nailing down 7s to a single thing is basically impossible. They’re unlikely to be happy in one place. Tantric practices will be appealing to them, as will practices from Dzogchen and Zen that point directly to awakening. But realistically they’re going to mix practices from various traditions, and many will struggle to settle down until they’re already far along the path.

8. Rinzai Zen. Unlike Soto Zen, which heavily emphasizes meeting the moment in stillness, Rinzai asks students to meet the moment in action. Rinzai teachers are notorious for doing wild things to help their students wake up, from shouting and hitting to asking them to answer impossible questions. 8s meet these moments, find themselves exposed, survive, and then discover that, in the end, everything is okay.
   (There’s also some interesting Enneagram theory-craft about how 4s and 8s are “the same” except that 4s turn inward and 8s turn outward, so it makes some sense they’d be on opposite sides of a pair of closely related lineages.)

9. Monasticism. Rather than best fitting a specific lineage, 9s are well adapted to monastic practice. Their desire to merge is acknowledged and contained by the monastic structure, and any lineage that offers that will serve them well. Even in lay practice, they’ll do well in more traditional groups that create the same kind of formal container that monastic practice provides. This structure can be found in many traditions, but, in the West, Zen is probably the most accessible and reliable option for getting what they need.

I’m sure more matchings work, and I know plenty of people practicing in lineages outside this mapping. In fact, I know plenty of 6s in Zen, which is surprising, because the 6 reaction to zazen is almost always the same: panic. And yet, sometimes, they stay. I’m sure you can find people of every Enneagram type in every lineage, as the teacher, student, and specific context matter far more than the general pattern of practice in a lineage. But, if you’re currently looking to take up a Buddhist practice and having a hard time finding your fit, I think it’s worth looking to your Enneagram type for guidance.

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• 7 Habits of Highly Effective People

• Getting Things Done

• How to Win Friends and Influence People

• I’m Ok, You’re Ok

What these books have in common, aside from being self-help, is that they’re attempts to help people make the transition from the pre-rational, pre-systematic thought most of us have entering adulthood to the rational, systematic, modern, and self-authoring thought of Kegan Stage 4.

This process is often plagued with difficulty, as Kegan himself explores in In Over Our Heads, and is especially difficult for people who master Stage 4 thinking in one area of their lives but struggle with it in others. Folks like doctors, lawyers, scientists, and engineers are masters of Stage 4 thinking by the time they graduate from college, but usually only within their domain of study. They can easily spend decades with their personal and social thinking trailing in Stage 2 or 3, and suffer all the more for it because they know more would be possible if they could just figure out how things work.

Thus, I was pleased to recently come across a copy of The Unwritten Laws of Engineering. Originally published as a series of three articles by W. J. King in Mechanical Engineering magazine in 1944, the book I found was a second edition with revisions and additions by James G. Skakoon. And although the original advice is now several decades old, it still reads well for professionals learning to operate at Stage 4 in their work lives.

The book is relatively short at just 60 pages, but in that space its direct, to-the-point style does a good job of explaining what should be obvious. Some of its advice includes such nuggets as:

• Confirm your instructions and the other person’s commitments in writing.

• Return your messages.

• Whatever your supervisor wants done deserves top priority.

• Meetings should be neither too large nor too small.

• Cultivate the habit of making brisk, clean-cut decisions.

• Regard your personal integrity as one of your most important assets.

• Beware of what you commit to writing and who will read it.

It ends with a brief discussion of how to analyze yourself, as a system, just like an engineer would analyze their work. It encourages readers to find their strengths and learn to exploit them, and also to notice that one’s passions and desires may not always lead to the happiest and best life.

I get the impression this book is a popular graduation gift. Maybe I would have seen a copy earlier if, despite the various job titles I’ve held, I’d been an engineer instead of a programmer. But I wish I had, both for myself and for the engineers I’ve managed who, despite years of experience, held themselves back by not applying the same systematic approach to themselves that they applied to their work, for it was only learning to treat myself as a system that began to learn how to take control of my own life.

That said, like most books in this genre, I’m sure it’s lost on the people who need to read it when they first do. The lessons one must learn to make the Stage 4 transition are complex, have to be lived, and can’t be picked up in an afternoon from a book, but the books do help! They plant the seeds of ideas in the minds of their readers, and as best I can tell, The Unwritten Laws of Engineering is as good at sowing as any book in the genre.

I know some of you read the draft version I posted on LessWrong as I wrote it. If you did, thank you, because your comments and feedback were critical in making the final version what it is (some of you even made it into the acknowledgments!). There are lots of changes since the draft, so if you read it before and thought “ehh, maybe there’s something here, but I don’t buy it”, I highly recommend reading it again.

If you’re not familiar with the book, here’s its thesis:

1. Our knowledge of the truth is fundamentally uncertain because of epistemic circularity caused by the Problem of the Criterion.

2. We manage fundamental uncertainty by making pragmatic assumptions that lead us to believe in the truth of claims that help us achieve our goals.

3. Consequently, the truth that can be known is not independent of us, but rather dependent on that for which we care.

4. That truth is fundamentally uncertain and grounded in care has far-reaching implications for many of the world’s hardest-to-solve problems.

The book argues for and develops these points in greater detail. It’s written for a general STEM audience, but I think it will be mostly of interest to rationalist and rationalist-adjacent readers. I especially hope folks working on AI and AI safety read the book, since I wrote it to document all the things I had to learn about epistemology to pursue my own previous AI safety research program.

I’ll have more book-related news in the next few weeks, as I’m planning an essay contest, and I’m actively working on getting the print and ebook versions together, with an audiobook to follow. For now, you can read it either in your browser or as markdown, and if you’d like other formats, please let me know in the comments.

I finished the second editing, and I’m now into copy editing. That’s also almost done, with just the last two chapters to go. Which means that, sometime in the next month, the book will finally, after a bit over 4 years, be complete!

I’ve decided to go the independent publishing route. The book market has changed a lot, even just since I started writing, and my book is at high risk of being too niche to support a run with a big, commercial publisher. Thankfully, in that same time, independent publishing has lost a lot of its stink as the book market has transformed away from mass distribution, so it’s no longer a low-status move to go independent. Thus, I’ll be retaining the copyright, publishing the book free online for anyone to read, and also have print and audiobook versions for those who would like that available for sale with most major book retailers.

Very excited to get the final version of the book into everyone’s hands, and then to get onto my next big project. Expect a full announcement on it soon, but to tease you now, it’s a conference, it’s about epistemics, and vibes, and it’ll be happening a little later this year. More details soon!

I’m a week in now, resting and recovering, but I sadly had to admit that I wasn’t going to hit my new, lowered target of just one blog post a month while I finish the book. Then it hit me, I could use Claude to do some research into concussions and write something short about that!

So I asked Claude to do some research into concussion recovery. Specifically, whether there’s anything useful I can do beyond the standard advice of “rest”. I already sleep and meditate, and I’ve been hearing more about psychedelics as treatments for brain injuries, so I had Claude to do a deep literature review on all three as concussion interventions. We focused on psilocybin because it’s the psychedelic with the most research about concussions available. The full report is here. Here’s what came out of it.

The three interventions are complementary, not redundant. All three reduce brain inflammation after injury, but through different biological mechanisms. Hitting the same problem from three independent angles is a well-established principle in pharmacology, and it tends to work better than hitting it from one angle three times as hard.

Each one is best at a different thing. Sleep drives the brain’s waste clearance system. During sleep the spaces between brain cells expand by about 60%, allowing fluid to flush out damaged proteins and metabolic debris, and nothing else does this. Psilocybin provides the most potent signal for growing new neural connections, with a single dose producing structural changes lasting over a month in mice. Meditation offers the best-evidenced stress and immune regulation, creating the upstream conditions that let the other repair processes work.

Psilocybin works around a problem the other two can’t. After brain injury, inflammation hijacks the raw materials your brain uses to make serotonin and diverts them toward toxic byproducts instead. This depletes serotonin while simultaneously causing further damage. Because psilocybin is chemically similar to serotonin, it can activate serotonin receptors directly, bypassing the broken supply chain entirely. No endogenous process can do this.

But the evidence is profoundly asymmetric. Sleep has robust clinical data and an irreplaceable biological role. Meditation has one concussion-specific meta-analysis showing moderate benefit and near-zero risk. And psilocybin has zero completed human trials in brain injury populations, with the strongest direct evidence being a single rat study.

So the actionable takeaways are, sadly, anticlimactic. Prioritize sleep above everything, and not just “sleep more” but actively protect it, because the injury itself disrupts the very sleep needed for repair. Meditate if you already do and consider starting if you don’t. And probably don’t take psilocybin for a concussion yet, because the biology is exciting but there’s no human data and there’re unknowns around safety in an injured brain.

The full research report with citations is here.

The first makes the claim that minimum viable AGI is already here. The second is my take on what to do about it.

I can’t understate how important it is to understand what’s going on right now with AI and the immediacy of the need for action.

That said, there’s only so much I can do about it, so I also have updates on the book.

Book Updates

I reached an important milestone yesterday: I finished revisions on Chapter 7, which is the last of the core chapters of the book. All that’s left is to do a revision pass on Chapters 8 and 9, which are “what’s next” chapters after having concluded the core arguments.

I have no idea how long they will take to revise. I hope not long, but they do contain a lot of words.

I really want to get the revisions finished and the book actively moving towards print publication soon, so I’m going to be taking a little break from blogging. Not entirely, but I’m going to switch to posting semi-monthly instead of weekly until I get all the revisions done.

Historically, I always write more than whatever target I set for myself, so I’ll probably write more. I just have to remember that the less I write here, the more progress I make on the book, and the sooner the book is done, the sooner I can focus on blog posts instead of book revisions.

I practice Zen in the lineage of Charlotte Joko Beck. Her teaching style was, for its time, radically non-traditional. In an era when talking too much about your inner thoughts and feelings was discouraged by first-generation Japanese-American Zen teachers, she believed Western students needed to practice a Zen that leaned on familiar psychological concepts to make sense. One of those concepts is what she called the “core belief”.

The core belief is a deeply held, usually unconscious belief about ourselves. It almost always feels like some flavor of “not enough”. It forms early, operates automatically, and powers the reactive, habitual, and often maladaptive patterns of behavior that make up most of what we call our personality.

The cruel trick of the core belief is that it reinforces itself. It tries to protect you from noticing anything that might confirm it, and by doing so actually generates more evidence in favor of it. For example, if you believe you’re unlovable, you might push people away so they can’t prove you aren’t worthy of love, or you might stay so anxiously close to them that no one has a chance to notice how they really feel about you. It’s a psychological trap that heaps suffering upon more suffering, and almost all of us have been ensnared in it since before we can remember.

Joko doesn’t advocate for getting rid of the core belief. In fact, she argues that would be impossible. Instead, it’s about becoming intimate with it, noticing it when it shows up, and learning to face reality rather than hiding from it. The more you do that, the less power the core belief has to control your life, and the more you are free of the suffering it causes.

But describing the core belief as a feeling of “not enough” is rather vague. You can sit for years, intellectually knowing you have a core belief, and never catch a glimpse of what your core belief really is. It’s possible to have so many layers of psychological barriers in place that you never allow yourself to see it.

In the Ordinary Mind Zen School that Joko founded, we practice getting past these barriers by paying attention to sensations in the body. Much like in Gendlin’s Focusing, we try to notice the physical sensations that arise when we react out of anger, fear, or desire. We become familiar with those physical feelings, then, let our minds name them. Sometimes the names we give provide surprising insights. Other times, nothing comes, and more noticing is needed. Over time, with the help of a skilled teacher, one can learn to work with their core belief and tease apart how it limits life.

Now, it’s pretty normal in Zen to do things like this from scratch with a minimum of conceptual frameworks. And I generally endorse this approach, but sometimes it’s helpful to get hints. Based on my understanding of the Enneagram, gleaned from Michael Valentine Smith’s series of posts on it last year (1, 2, 3, 4), I think its nine types provide a map to common patterns of core beliefs, and may help a person better practice with their core belief when noticing alone leaves them stuck.

The Enneagram is a Map of Suffering

Over the years, I’ve occasionally taken Enneagram tests, and every time I found the results unhelpful. I’d get categorized as some type, be offered some explanation of what it means, and while it seemed like it might be true, it all fell flat for me. Am I a 9? A 3? a 1? Who knows! The outcome seemed to change based on my mood. I had little reason to think that the Enneagram was useful.

Michael helped me see value in the Enneagram by reframing it, not as a personality classification system, but as a map to how and why we suffer.

In his framework, each person has what he calls “Essence”, which is something like your true nature, the awareness and aliveness you had before reactive personality took over. Essence naturally expresses certain qualities, like love, clarity, peace, power, and freedom. But when Essence gets overwhelmed in early life, it creates a mechanical personality to stand between itself and the world. That personality tries to mimic Essence’s qualities, but it can only produce toxic imitations, and those imitations create self-reinforcing downward spirals.

He tongue-in-cheek summarizes the Enneagram as asking: “In which of these nine ways are you most screwed up?”

Reading his posts, I couldn’t help but notice that Michael’s “downward spiral” was not too different from how Joko describes the workings of the core belief. In fact, I think they’re pointing at the same mechanism, but are coming at it from different angles.

The Enneagram says personality tries to replace an essential quality, and fails because the replacement is mechanical. Joko says that the core belief generates reactive patterns that try to protect us from acknowledging it. Both say that these behaviors create lock-in, double down on what’s not working, and create a self-reinforcing loop of suffering.

What’s neat about the Enneagram is that, unlike Joko’s intimately individual approach, it gives you a map to the essential qualities your personality is trying to mimic. If the parallel between the Enneagram and Joko’s teachings holds, then each Enneagram type corresponds to a class of core beliefs. I might phrase those as:

• Type 1: “I’m not good/right enough”

• Type 2: “I’m not lovable enough as I am”

• Type 3: “I’m not valuable enough without proof”

• Type 4: “My inherent worth is missing or damaged”

• Type 5: I’m not equipped enough to handle the world directly”

• Type 6: “Nothing is reliable enough to trust”

• Type 7: “What’s here isn’t enough”

• Type 8: “I’m not solid/real enough”

• Type 9: “Things aren’t okay enough to fully engage with”

Of interest to me is that this mapping can give greater specificity to Zen practice. It can be hard to simply sit with not-enoughness. You have only a vague idea what you’re looking for, and people are different enough that the way one person talks about their feeling of not enough may sound totally foreign to you. The Enneagram helps explain this, because different people really do have different styles of core belief that feel quite different from the inside.

That said, I see some danger in the Enneagram. It’s a system for putting names on things, and Zen is ultimately about seeing through how our mental constructs imprison us. The self is not a fixed thing. Our stories about ourselves are just more thoughts about whatever is really going on. The Enneagram risks becoming a new way of formulating a self to latch on to rather than a way to become free of it.

To be fair, Michael himself warns about exactly this in his series. People who get into the Enneagram often start trying to explain everything in terms of it, and then start contorting their behavior to fit their type. He recommends holding your type “extremely lightly” and measuring its value by a single criterion: does viewing yourself this way make your life more wholesome?

That’s a good test, and it’s the same test I think Joko would apply. Is your practice making you more open, more responsive, more alive to what’s actually happening? Or is it giving you a more sophisticated story about yourself? The Enneagram is useful exactly insofar as it helps you see through personality. It’s harmful exactly insofar as it helps you solidify it. If you find yourself using your type to explain your behavior rather than to notice and release it, set the Enneagram down.

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Finding My Type

After reading Michael’s series, I got interested in what type I might be, since if my theory was right, it will help me in my Zen practice. When I’ve taken Enneagram tests, I’d variously score as a 3, a 5, a 7, or a 9. And if I’m honest with myself, I see something of myself in all the types. Hard to do much with that!

But as Michael argues, the tests are just looking at surface-level traits and don’t do a very good job of detecting Enneagram type. What you actually have to do is figure out which type helps you unwind the reactive downward spiral. As I think of it, you need to ask yourself: which type’s need, if it were fully met, would make you truly and deeply happy, and not because your need was incidentally met, but because your need was met fundamentally?

This is easier explained with an example. As I said, I often test as various types. Sometimes I test as a 3, meaning I need to prove I can achieve greatness. Other times I test as a 5, meaning I need to show off how much I know. But notice how I phrased those. I didn’t say I desire achievement or knowledge, I said I need to prove/show off. And you know what type needs to demonstrate personal specialness? That’s right: type 4.

As I think of it to myself, I’m happiest when my inner nobility is allowed to shine. Everything else is incidental. I’m smart enough that I can let my nobility shine by showing what I know. I’m capable enough that I can let it shine through achievement. In fact, I can make any of the types fit so long as it’s a means to showing off my specialness. I feel like this explains a lot about me.

What’s interesting from a Zen perspective is how a type 4 core belief maps to the central misperception that practice addresses. The 4’s spiral is powered by a search for inherent worth that was never missing. That’s basically what “seeing your true nature” is all about in Zen: recognizing that what you’ve been searching for was here all along. All you have to do is stop searching, and you’ll find yourself!

Now of course, following Michael’s advice, I hold this all lightly. Maybe I’m wrong about being a 4. Maybe someday I’ll find it makes sense to think of myself as another type. The point is not to be identified with a type, it’s to use the type to make sense of myself and point the way to actions I might take that would make my life better.

And the same is true if you want to try using the Enneagram. I suggest reading Michael’s series, and if you’re interested in learning more about Joko’s idea of the core belief, I suggest picking up her most recently published book, Ordinary Wonder.

What’s the Great Matter? It’s the question you can’t answer. It’s the fear you feel when you contemplate your own death. It’s the void lurking at the center of your existence, and no matter how hard you try, you can’t see into it. You’ve lived with it for as long as you can remember, fighting against its friction with your every action. It can’t be pointed at directly, but you know it’s there because it’s in the place you can’t look.

That’s all rather mysterious, and thankfully some people have managed to grapple with the Great Matter enough to say a little more. They often talk about non-dual experience, of crossing the divide between the relative and the absolute. They say things like there’s no separate self and that all is impermanent. And if they’ve read the right websites, they might even describe the Great Matter as the contradiction inherent in the intuitive self-model, and say that to resolve the Great Matter is to have the insights that transition you into a persistent, non-symbolic experience of existence (PNSE).

Or, in short, to resolve the Great Matter is to become enlightened.

But the longer it’s been since the Great Matter was resolved, the less I like the word “enlightened”. I did a whole video essay about it, but in short, the main problem is that “enlightenment” implies a permanent state of attainment and carries misguided cultural connotations. Other words like “awakened” drop some of that cultural baggage, but unfortunately keep the attainment framing.

And you might be saying to yourself, why would an attainment framing be bad? Clearly something has been attained! But, the only thing attained is a resolution of the Great Matter itself, which is the act of having an insight and having that insight spread deeply through your entire being, nothing more. The rest has to come later. All that resolving the Great Matter does is remove the obstacle that was blocking the way on the path to freedom from suffering.

And if you want to be free of suffering, you have to put in the work. First, you have to put in the work to resolve the Great Matter, which often involves untraining many of your maladaptive habits. It requires grappling with your addictions, your traumas, your hangups, and your insecurities. And then, after the Great Matter is resolved, you have to continue that work, but now on a deeper, more subtle level than was possible before. It does feel easier, because you no longer have to deal with both the habituated mind and the Great Matter, but that feeling itself can become a trap that will ensnare you if you aren’t careful.

Now, some people who resolve the Great Matter do so while living in a monastery or hermitage, or move to one after such resolving. In such a place, one has the opportunity to minimize decision making and planning. And when there’s no decisions to make, there’s no need to model the self, and so the constructed self-model can be let go and forgotten, replaced by a mind that only concerns itself with this moment. That can be nice, especially if done for a limited time to strengthen one’s practice, but it comes at the cost of helping the world.

To help the world, you have to live in it, and that means constructing a self-model to make the predictions necessary to plan and take actions. The best one who has resolved the Great Matter can do, if they are committed to benefitting all beings, is to find a way to live holding that self-model lightly. To see, in each moment, that the self and the not-self views are equally real, for both are needed to tackle the great many challenges facing our world.

I’ve left out many details you’d probably like to know. That’s because I write this post with some hesitation. Although this is not the first time I’ve publicly admitted to being “enlightened”, it is the least obscure and most easily found. But I decided to take the risk, because I feel that it’s been long enough that I can speak confidently of my own experiences, however they are labeled, and because by speaking about those experiences, I may be able to help others.

When I had not yet resolved the Great Matter, I was very confused about it. Some people wrote some straightforward things that were confusing. Other people wrote confusing things that were straightforward. I needed all the help I could get from others pointing the way for me. Now it’s my turn to help others by pointing. This is one attempt, and I hope it proves useful.

But I think the word has legs. I just have to figure out what it actually means!

On the surface, it’s obvious. It’s the combination of “vibes” and “epistemics”, so more or less naming the core idea of the post/meta-rationalist project. But again, what does it actually mean? It’s easy to point at a large body of work and say “I don’t know, whatever the thing going on over there is”, but much harder to say what the thing actually is.

So to start, let’s talk about epistemics. What is it? I see people using the word two ways. One is to mean the way we know things in general. The other is to mean the way we know things via episteme, that is knowledge that’s reasoned from evidence, as opposed to doxa and techne and many other ways of knowing (if those Greek words mean nothing to you, I highly recommend reading the post at the link before continuing). Unfortunately, some people equivocate between epistemics-as-knowing and epistemics-as-knowing-via-episteme to give the impression that episteme is the only good way to know anything. That, to me, is a problem.

I think it’s a problem because such equivocation discounts valuable sources of knowledge that aren’t easily made legible. Now, to be fair, there’s some reason to do this, because the pre-rationalist epistemic stance says legibility doesn’t matter and logic is just a means to justify one’s preferred ends. The rationalist stance is largely that everything that can be made legible should be, and that which cannot be made legible needs to be treated with great caution because that’s how we slip back into pre-rationality. So I understand the desire to equate epistemics with episteme (and, etymologically, the English language tries very hard to do this), but I also find it frustrating because it encourages excessive devaluing of other ways of knowing, especially metis, techne, and other forms of knowledge that are less legible.

That’s where the vibes come in. They can rescue us from an excessive focus on episteme and temper the excesses of legibility. But what are vibes and how can they help?

Vibes are the embodiment of what we care about. The stoner, for example, has stoner vibes because they care about chilling and feeling good. The Christian has Christian vibes because they want to do what Jesus would do. And the rationalist has rationalist vibes because they care about knowing the truth with high predictive accuracy. For any vibe, there is always something the person expressing it cares about deeply that causes them to have that vibe.

This matters in epistemics because knowing is contingent on care. I make this argument in detail in Fundamental Uncertainty (currently in revision ahead of publication), but the short version is that we have a mental model of the world, truth is the degree to which our mental model is accurate, we want an accurate mental model because it’s useful, and usefulness is a function of what we care about, thus truth is grounded by and contingent on care. And since vibes are the embodiment of care, vibes have an influence on the act of knowing, hence, vibestemics.

(If this argument seems handwavy to you, it is. You’ll have to read the book to get the full argument because it takes about 10k words in the middle of it to lay it all out. If you want to read the first draft for that argument, it’s in Chapter 5, 6, and 7 which start here. Alternatively, although I think “Something to Protect“ does a poor job of emphasizing the epistemic relevance of care in favor of explaining a particular way of caring, I read it as ultimately claiming something similar.)

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Okay, but that’s the theoretical argument for what vibestemics is. What does it mean in practice? Let’s dive into that question by first considering a few examples of different epistemic vibes.

Woo: The epistemic vibe of woo is that whatever’s intuitive is true. Woo is grounded in gnosis and largely eschews doxastic logic and careful epistemic reasoning. That said, it’s not completely devoid of epistemics. It’s definitionally true that whatever you experience is your experience. Unfortunately, that’s roughly where woo stops making sense. It interprets everything through a highly personal lens, so even when it leads to making accurate predictions, those predictions are hard to verify by anyone other than the person who made them, and woo-stemics easily falls prey to classic heuristic and bias mistakes. This severely restricts its usefulness unless you have reason to fully trust yourself (and you shouldn’t when it comes to making predictions).

Religion: The vibe of religion is that God or some other supernatural force knows what’s true. Knowledge of what God knows may require gnosis, or it may be revealed through mundane observations of miraculous events. Although not true of every religion, religious epistemics can be a friend of logic, and many religions demand internal logical consistency based on the assumptions they make. Sometimes these theological arguments manage to produce accurate world models, but often they have to be rationalized because the interpretation of the supernatural is fraught and we mere mortals may misunderstand God.

Science: Science as actually practiced by scientists involves empirically testing beliefs and updating them based on evidence. The vibe is pragmatic—build hypotheses, test them, see what happens, and revise accordingly. The only problem is that science requires the ability to replicate observations to determine if they’re true, and that’s where it hits its limits. When events can’t be observed or can’t be replicated, science is forced to say “don’t know”. Thus, science is fine as far as it goes, but its vibe forces it to leave large swaths of the world unmodeled.

Rationality: The vibe of rationality is to be obsessed with verifying that one really knows the truth. This has driven rationalists to adopt methods like Bayesian reasoning to make ever more accurate predictions. Alas, much as is the case for science, rationality struggles to deal with beliefs where predictions are hard to check. It also tends to smuggle in positivist beliefs for historical reasons, and these frequently result in an excess concern for belief consistency at the cost of belief completeness.

Post-rationality: The post-rationality vibe is that rationality is great but completeness matters more than consistency. Thus it attempts to integrate other ways of knowing when episteme reaches its limits. Unfortunately, how to do this well is more art than science, and there’s a real risk of getting things so wrong that a post-rationalist wraps back around into pre-rationality. Arguably this is what happened to the first post-rationalists (the postmodernists), and it continues to be a threat today.

What I hope you pick up from these examples is that different epistemic vibes are optimizing for different things and making different tradeoffs. Although it may seem strange, especially if you’re a rationalist, that someone could have a good reason to ignore predictive accuracy in favor of intuition or dogma, for those with woo and religious vibes that choice is locally adaptive for them. They similarly look back at you and think you are deeply confused about what matters, and this is a place where arguments about who’s right will fail, because they’re ultimately arguments about what each person values.

All that said, it’s clear that some vibes are more epistemically adaptive than others. Accurate world models convey real benefits, so adopting a vibe that leads you to develop better world models is usually a good move. This, incidentally, is what I would argue is the pragmatic case for post-rationality over rationality: it’s rationality plus you can break out of the rationalist ontology when it’s adaptive to do so (though admittedly at the risk of it becoming rationality minus the guardrails that were keeping you sane).

And this ability to shift between vibes is why I think having a word like “vibestemics” is valuable. When we can only speak of epistemics, we risk losing sight of the larger goal of living what we value. We can become narrowly focused on a single value like accurate model prediction, Goodhart on it, and forget to actually win. We can forget that knowledge and truth exist to serve us and our needs, not the other way around. Vibestemics invites us to know more and better than we can with episteme alone, if only we have the courage to let our grip on a single vibe go.

Chapter 7, as you may recall if you read the first draft, is both the “cybernetics chapter” and the “tie everything together” chapter. Originally it was largely based on the two posts where I first worked out these ideas, but as I’ve been revising, I discovered that it contained both a lot of extraneous material and didn’t have quite the right focus for where it sits in the book. These were both problems I knew about when I wrote the first draft, and now in the revisions I have to solve them.

As a result, it’s been a slog to find the right way to present these ideas. I’ve tried maybe 5 different approaches. It takes time to develop them out enough to see if they work. I’m hopeful that the 6th approach will be the final one, but it’s not done yet, so no promises.

Medium

Hey, did you know I used to run a blog on Medium called Map and Territory? It originally started as a group blog for some folks in the LessWrong 1.0 diaspora, but the group aspect quickly collapsed after LessWrong 2.0 launched, so then it was just me. (All my posts from it are now mirrored on LessWrong since I trust it more than Medium in the long run.)

Anyway, every few months somebody, usually this guy, references my most popular post from the Map and Territory days. It’s titled “Doxa, Episteme, and Gnosis”, and it still gets about 100 new reads a week all these years later. I’ve tried a couple times to write new versions of it, but they never do as well.

The “Many Ways of Knowing” post from two weeks ago was the most recent evolution of this post, though this time excerpted from the book. I like it, and I think it fits well in the book, but it still doesn’t quite capture the magic of the original.

The original succeeds in part, I think, because I was naive. I presented a simple—and in fact over-simplified—model of knowledge. It’s accessible in a way that later revisions aren’t because it’s “worse”, and I suspect it’s helped by putting three Greek words in the title, which I am pretty sure helps with SEO from students trying to find out what these words mean.

Anyway, this is all to say I got some more posts lined up, and hopefully I’ll at some point be naive enough to write another banger.