Ultimately, though, when I’m assessing someone’s work, I try to ask the following question. Is this teacher, pastor, therapist, facilitator, coach, whatever, on average, according to my best guess, moving people closer to liberation, or further away?

And there aren’t actually many spiritual teachers who are so bad that their effect on the world is definitely net negative. Even some of the looniest loose cannons on the scene, the most corrupt and megalomaniacal (Jeffery Martin) often have positive effects on balance. The wisdom of Chögyam Trungpa lives on, even though he was massively unethical at times. Spiritual teachers aren’t competing versus a wise mass culture. They are competing versus TikTok and Fox News, popular astrology and fad diets. It takes work to be worse than that.

This doesn’t mean we should automatically forgive horrible conduct. As individuals, we ought to strive for exemplary behavior, and expect the same of others who do spiritual work.

However, there is the following question. Who do we need out there, if we want to awaken all beings? My answer is:

We need everyone.

Frequently, I hear backchannel spiritual community gossip along the lines of: “I tried studying with teacher A, but they had such obvious blind spots. Then teacher B straightened me out.” Later, I then hear the same story, but reversed, where teacher B is the obviously blinkered one, whose faults were illuminated by the teachings of teacher A.

We need teacher A and teacher B.

We need the spiritually gifted Mormon sex therapists. We need the heterodox bodyworkers and the near-psychic embodiment wizards. We need contemplative accounts from Christian mystics and stridently atheist polyamorists. We need pricy spiritually-flavored executive coaching programs. We need old-school Theravada teachers who are not for sale at any price.

We need psychedelic dropouts, and people who correctly point out that drugs can’t be the ultimate answer. We need spiritually-informed psychotherapists who urge the meditators to look at content, and meditators who encourage the therapycels to ignore their stories sometimes, or look at the emotions underneath.

We need Neo-Tantra weirdos to teach people emotional release and butt exercises, and we need DBT therapists to teach emotional regulation and theory of mind.

We need IFS artistes to provide space for others to encounter their parts and achieve greater inner coherence. We need Zen teachers who can remind people to just be open and quit it with the fragmentation.

We need scientists working avidly, providing the neural correlates of awakening. We need irascible naysayers who point out that awakening is probably not something that can be fully mapped by scientific understanding.

We need non-dual YouTube influencers with cringe taste in video effects. We really need Frank Yang to make many more videos. We need Cheetah House to help with meditation side effects caused when unbalanced people get too high on spirituality content.

We need the massively scaled meditation hucksters who claim that their techniques work for everyone. We need the angry blog posts by people who point out that these techniques do not, in fact, work for everyone, and that real spiritual work doesn’t survive scale.

We need autistic teachers who carve up the contemplative landscape into a million sub-techniques, like Shinzen Young, and poetic teachers who tell you to just relax and wake up, like Adyashanti.

Sometimes, I hear complaints about the overabundance of professional spiritual types. Well, I’m in Berkeley, the white hot center of it, and I can tell you that we are nowhere near saturation on effective meditation teachers, or spiritual workers generally. I don’t have enough good people in my referral network.

Meanwhile, lots of smart, informed people still don’t believe in jhana. That’s like not believing that ibuprofen is real.

I think I’ll believe we are saturated when awakening is viewed, in popular culture, like noob gains in lifting. It is commonly understood that a novice lifter can double their strength within months of training, that’s in the water. There’s plentiful information about all the different programs you can do, and how to rehab injuries you might get along the way. Sure, there are arguments about the best method. But a general picture has cohered, and is common knowledge. Awakening isn’t there yet. Not nearly. I’d like to ask people on the street what they think of spiritual awakening, and hear the response, “Yeah, I know I could open my heart and relieve something like 90% of my suffering and be much happier and more prosocial if I did some years of serious spiritual practice. I understand that I can have a deep relationship with the transcendent that can transform me and my relationships and all of my perceptions, I know that’s out there for me.”

I believe enough in the intelligence of the world that, through the existence of more and more spiritual voices, rough points of consensus will emerge that could massively benefit humankind.

We’re not there yet. We need you to help us get there, even if I find you personally annoying.

Try it now. One minute. If you like that, add more minutes. See if the emotion can enter and pervade the breath like incense.

This framing is designed to counter the main failure mode of heart practice, which is to make it aspirational. People hear about “loving-kindness” practice and they think, “alright, time to pretend I have the emotions of Jesus, time to love dictators.” You may get there, but you have to begin with your average post-industrial heart.

Take the emotions that already sweeten your life in small quantities, and notice that they multiply when given delicate attention. If the phrase “may all beings be happy” has zero here-and-now resonance for you, ignore it. Instead, pick up the appreciation for how music sounded when you were in college. Or the bittersweet transience re: the beloved friends who are off living separate lives somewhere. Gratitude that you are still allowed to be in society despite your previous failings. Whatever is effortlessly opening when you turn towards it internally. I also introduce heart practice as “corny feelings” practice. You have at least one of those within reach, right?

If your mind is jumpy, try conjuring a feeling out of a jumpy series of impressions. For awhile, I really enjoyed thinking of all the people in my life fleetingly, inwardly repeating “good job,” until I was awash in enough feeling to hold it as a concentration object. The technique that works for you might be stupid.

If your experience is tinged with sadness, that is fine. Also, I disagree with traditional Buddhist guides that tell you never to confuse heart practice with romantic or sexual feelings. Pick whatever is rich and involving as an object, right now—as long as you can stay with the feeling itself and not any attached fantasies. Stay with the feeling. And gently notice how pleasant and engaging that is, sliding into a relaxed flow state. That’s all you need to do.

When the feeling is large enough that you can let it overtake you like a tidal wave, do that. Let the feeling start steering. Getting there involves mastering your emotional system, which is more like befriending an animal than following a recipe. Force won’t work. Gently experiment with different coaxing. You will learn, in time, what stirs you. Some people, I’m told, get blissed out by remembering their favorite equations.

It might be completely insane, what happens to you. Heart practice is a great onramp to jhanas, the druggy bliss states you may have heard about. If you do heart practice for some years, as your main meditation or as a supplement, you might find yourself default loving everyone, even the people who annoy you. Approaching strangers as if you love them, because you do, has an effect. You’ll empathize even with your enemies as you are smiting them. With significant training, MDMA will seem like a mostly superfluous compound, just a stimulant atop your normal emotional spectrum. (Really.) You won’t be blissful 24/7, challenging emotions will still arise. But you can get closer than most people would believe possible to embracing everything, while still functioning sensibly.

You don’t have to believe me, any more than people who go to the gym have to believe that, with repeated application of resistance, the average person becomes muscular. You just have to show up. Feel what is rich and involving today, on many days.

If there aren’t any rich feelings available, you might be tensed up in a state of resentment. Try this forgiveness meditation, or try having the difficult conversation you’ve been postponing.

If there’s a big screaming billboard of anxiety or shame in the way of any other emotion, and you’re mentally stable overall, try focusing on the screaming billboard as if it’s a positive sensation that you want to appreciate every detail of. Just the physical parts of the sensation, not the interpretations. Could be cool, this book might help.

If you’re not afraid of the G-word, try the feeling that results from the phrase “remember that God loves you.”

If you’re sick of feeling positive emotion alone, if that feels a little insular and masturbatory, try tonglen. I fucking love tonglen.

There may be side effects to heart practice.

What side effects?

Meditation side effects generally fall into two categories.

The first category, not typically caused by heart practice, is perceptual weirdness—for example, after dry vipassana, where you carve sensation up into its constituent parts, sometimes reality will feel buggy, like a stuttering film strip.

The second category is “congratulations, you have been forced to do some helpful therapy.” Material is produced which has to be worked on. Mostly, the side effects of heart practice are like that. Behold these oscillating cones:

Distraction gets an undeservedly bad reputation. It’s a helpful method of concealing difficult things we don’t yet wish to confront. ADD behavior is an emotional regulation strategy, and subtler forms of distraction are useful ways of obscuring, say, the knowledge of death and transience.

After heart practice, your attention will be more open and stable, so you’ll contact the difficult parts of the human experience. Luckily, you’ll be armored with a sense of love and safety after a good sit. But the emotional glow won’t necessarily persist—so you might have to encounter these difficult sensations without that armoring. This can be done, but it’s intense, and you’ll have to feel out your capacity as you go. It’s like being sent out on a mountain with a pack full of delicious food. Halfway up you might run out of lunch and find yourself hungry out there. Before doing intensive heart practice, make sure you have someone who can support you when you’re halfway up, a teacher or friend or therapist or parent or whoever, someone who can hear your tantrums. If you can’t allow yourself vulnerability, I don’t advise this practice.

If you find yourself taking on too much, feel free to re-enter distraction. Most people are experts in checking out—draw on that skill when necessary. Have some carbs and video games until you develop more equanimity.

There is a far side beyond, where every sensation can be met with open tenderness. Heart practice will get you moving in that direction. Complete intimacy with all experience is an unusual place to live from. You will be, in some facets of your emotional experience, unrelatable to many people. This is the tradeoff; you will know that, at bottom, the mind is wonderful, in a culture that frantically tries to persuade you that life is essentially tragic. You will enter the small weird team of happy people.

Photo credit goes to Daido Moriyama.

Self-help books are, at their best, personality transmission devices. Consuming the self-help books that have changed my life, like The 4-Hour Workweek and Existential Kink, changed me not because of any one tactic, but because the human gestalts within were helpful additions to my default tendencies. (This is why reading self-help books cover-to-cover tends to be more helpful than just grazing them for tips, even though a summary of the average self-help book could fit on a napkin.)

While our book contains good tactical advice, my real hope was for You Can Just Do Things to capture Cate’s unusual mind-shape, such that readers could download a useful sliver. I’ve improved as a result of living with Cate, and I would like to be the only person living with Cate, but I also want other people to have a similar opportunity for improvement.

Cate has accused me of writing about her as if she’s a mythical creature. This is a fair accusation, and I can report that she’s a human being. We’re going on four years together, which makes me the world’s foremost expert on her foibles and irrationalities.

However. My assessment of her overall competence and personal qualities, which I wrote about breathlessly in our early days, is the same as ever. She continues impressing me. I continue asking: what makes Cate so different? What makes her so fucking good at everything? I have come to an updated brief answer: extremely high confidence, extremely low defensiveness. In other words, Cate both believes that she can do anything, and believes that she’ll get there by being completely open to feedback, rather than clinging to competence as an identity.

If Cate’s worst enemy lobbed an insult at her, I think she would stop to ask: is there a good suggestion for improvement in there? Almost nobody is like this.

Lately we’ve been watching a lot of Top Chef in the evenings. It’s an opportunity to polish our Padma Lakshmi impersonations, but it’s also an opportunity to see how poisonous defensiveness is. There is a trait shared by almost all the top competitors: they almost never pout in response to the criticism of the judges. They listen. Perhaps they don’t agree, but they search their conscience about whether the judgement contains useful information. Meanwhile, those who are doomed to early elimination are indignant when challenged. They greet feedback like “it was mushy” with disbelief or excuses, like, “this is just my style of food.”

Cate’s journey as a writer is an example of the opposite of defensiveness. People sometimes ask me: how much do I help with Cate’s writing? The answer is that my role has shifted over time. At the book’s inception, I was helping a lot—nearly all of the first vomit draft (which she has completely overwritten) was mine, based on notes from our conversations. However, I barely touch her writing anymore. We give each other about the same amount of writing feedback. She has learned almost all of the relevant skills I have—I’m no longer the main writer in the relationship.

Previously, friends and partners have viewed my writing ability as a gift to envy, a mutation they couldn’t possibly acquire. I don’t think that perspective ever entered Cate’s mind. She just observes. Since our relationship began, through viewing my early drafts, watching me work, and asking me questions, she has relentlessly downloaded the viewpoint that allows me to be creatively productive and non-neurotic. When I read her an excerpt of something I admire, and she doesn’t immediately get why I’m so impressed, she asks: “why do you like that,” and she scans for nutrients she can absorb. Later, I see little glints of them turning up in her work.

This is how anyone should act if they had the perspective “Sasha is a better writer than me, I want to learn why, I’m going to maximize my learning rate until I’m just as good.” But nobody else who’s been close to me has done this simple thing, despite the fact that many expressed a desire to learn.

One of the many lovely benefits of our marriage is that I really don’t know what Cate is going to do next. Assuming this book gets the reception it deserves, “public intellectual” would be an easy lay-up for her at this point, another addition to an already surprising list of past professions. She’s already done the TEDtalk, and could open up a fancy consultancy in a second flat. She might spend some time doing this, but I find it hard to believe that I’ve seen the last plot twist, or even the next-to-last. She’s too smart to want an identity that would require defending.

If you are not one of those people, but you’d like to learn more about meditation of this sort, I’d recommend reading:

Original Love by Henry Shukman

The Science of Enlightenment by Shinzen Young

These resources are good if you’re just starting a meditation practice:

Some people find this essay I wrote helpful

This short essay is incredibly good

Tucker’s book is great

Charlie’s book is great

If you’ve started having profound spiritual experiences, and you haven’t read End of Your World, do yourself a favor and go read it. It’s pithy, fun, and deeply helpful, perhaps the only really accurate book about the deep end of meditation practice. Adyashanti is one of the most important humans in my life even though we’ve never met, and I know a bunch of other meditators who feel the same way.

The following short essays are written in the spirit of this great/bizarre meditation resource, which I partially agree with, but, moreso, admire. (It’s huge and forbidding, but has some amazing passages—search for “The state, process, and physical environment of the system are also its plans and goals.” for the beginning of a particularly inspired moment.)

The keep it up game

Sometimes, I think the spiritual path is really complicated. There are all these diverse skills to master, layers of ego to work through, constant opportunities to attempt a more ethical life, or wonder how to do so.

And then sometimes I think it’s actually very simple. What you are trying to do is lose a game.

You know those keep-it-up games that all children naturally reinvent? Where the floor is lava and you need to keep hitting a balloon or a ball so it doesn’t hit the floor?

The vast majority of humans are wired to play a game like this with experience. Raw experience is scary. There might be a lot of emotions down there. Perhaps there’s less control than you think there is. Perhaps you are a little fucked up inside, and not living up to your values. There’s also the fact of ever-present transience, which reminds us how soon we will vanish, along with everything we hold dear.

Reasonably, we avoid going there. And so we play a keep-it-up game. We kick the balloon of mind away from bare experience. Masters of this game spend days relitigating arguments that already happened, or arguments that haven’t happened yet. Or watching short form video constantly, or compulsively optimizing themselves in some fashion. Whatever it takes to get away from the gritty immediacy of being here.

Perhaps this is unsatisfying to you. And so you take up meditation, or another form of slowing down, and get a little worse at the keep-it-up game. You get closer to bare experience, and start noticing how painful and tight your avoidance mechanisms are. You start having more and more interactions with the fullness of emotion, which is wrenching and wonderful.

Some people then wonder: hey, how deep does this go? And they read a bunch of books about spirituality, and master a bunch of meditation techniques. Experience becomes amazingly psychedelic, and you find out that this psychotechnology has endured through millennia for a reason. It is undeniably potent.

But at this point you are still playing the game. The balloon is allowed to get pretty close to the ground, but every time it almost drops, there is a reassertion of identity. Like: “I’m so open to my emotions now, wow, it’s a shame that not everyone is like me.” Or: “My awareness is so expansive and beautiful, surely this is the spiritual awakening that I’ve been told about.” Each of these assertions is a subtle tap on the balloon that propels it upwards just long enough. This is a reasonable place to hang out.

But perhaps, one day, by the grace of God, you lose the game. The balloon hits the floor. Which feels like it should result in annihilation—the destruction of your precious identity as a meditator, along with the destruction of everything else. You lost the game! Isn’t the game all there is?

Strangely, though, life does not end with this annihilation. Instead, life is beautifully renewed by the hilarious knowledge of this game you’ve been playing, the whole time. It becomes extraordinarily funny how much your default setting was to flee from beauty, relief, and joy. Your whole life was about making yourself happy and you were not even good at it.

From then, you can do whatever you want. My life looks pretty similar to what it was before I lost the game. I am just more eager to help, because I’m aware of how painful the game is, and now that I’m not as busy playing it, I have more energy for other people.

I still kick the balloon around, because you sort of have to, to get along in society. But it feels lighter and easier when it’s not life and death, it’s just a balloon.

You actually do have to want it

Occasionally you will hear someone spiritual say, “spiritual ambition is dumb, you shouldn’t be meditating to get things,” or “just accept how everything is now.” To which I say, lol, lmao. Like obviously you actually want something out of spiritual practice, right? You want to have a completely different relationship with this life, and building this relationship requires real work. Without a spiritual yearning, you would not be practicing (or paying attention to my opinions about practice, certainly). “The secret is not wanting anything” is nonsense.

…On one level! But on another level, statements like this are extremely helpful: as practice pointers. The aim of statements like these is to avoid the failure mode of future-oriented meditative practice. In future-oriented practice, which is typically destructive, you are trying to aggressively bend your bodymind into a different shape, the shape you think it ought to be when you become spiritual, rather than lovingly meeting your bodymind where it is, thus changing your relationship to it.

So how do we find the synthesis between these points of view? It’s actually simple. The spiritual yearning, the desperate want for something else? Treat these as present-moment phenomena to be welcomed, opened to, examined, lovingly encountered. That want to be somewhere else is fascinating, if you start looking at it, really looking at the sensations composing that yearning. Where do you think you’re going?

A mundane view of the powers

Here’s a message I heard from serious meditators: “hey, you might get spiritual powers from meditation. But they’re a peril and a distraction more than anything. Just keep sitting.” I always thought this was woo-woo hogwash. And then it happened to me, but not like I expected. And it turned out to be an important warning.

How do I understand this now? Well, let’s say that on the meditative path, you are switching between two reward functions, two ways of gaining satisfaction.

Default reward function: “I have to get what I want to get! I just have to. That’s the important thing.”

Spiritual reward function: “All will be well. All manner of things will be well. Implicit in this is the realization that me and my wants are not so ultimately important, this identity is just an outfit.”

Since the meditative path gives you real benefits—like increased emotional intelligence, a greater ability to be present with people, etc—sometimes you will unlock an ability that makes it much easier for you to fulfill your default reward function. Like intense powers of concentration, or greater charisma, or something like that. This will create a natural temptation to become a cool spiritual person who is good at fulfilling your wants that way. And there’s nothing wrong with this, as a phase to hang out in for a bit, maybe a few years if you want. But it’s much less pleasant, in my experience, than moving to the latter reward function, which involves deeply interrogating your wants, in a way that requires humiliating self-honesty.

A huge amount of the New Age scene is people stuck in this cul de sac.

Your ego structure just will co-opt the spiritual path

You might read the above essay and think, “aha, great, I just won’t let my spiritual search be hijacked by my ego-level wants!” The bad news is it doesn’t work like that. How it works is that your ego structure will co-opt the spiritual path, and in the process, you will learn so much about the pain inherent in that way of being, and thus become increasingly willing to choose something else.

For example, as an Enneagram 7 with a side of 3, I was after two things in the spiritual path, not always consciously:

1. To always have fun/good experiences

2. To be a cool shiny spiritual person

And meditation gave me some of those things! But imperfectly. Oh no! You cannot always make your experience good, no matter how skilled you are as a meditator. And the more validation you get, the more you’re aware of the pain of lack that’s driving the search for validation. So I was brought into deeper and deeper contact with my stupidity, until release felt like a more tempting option than carrying on the way I had been.

I think there is no escaping this kind of self-confrontation.

In favor of insane Southeast Asian high standards

The phrase “enlightened” or “awakened” is, confusingly, used to refer to these two things.

1. Someone who has been through a particular mental event—a massive reduction in the part of consciousness that could be called “the separate self,” typically resulting in a shocking increase in well-being, and a dramatic change in perspective on life.

2. Someone who has reached a state of unusual moral perfection.

Being 1 is rare, but less rare than being a chess grandmaster—certainly tens of thousands, and maybe hundreds of thousands of people qualify, by my estimation. I’ve now met dozens of people who meet criterion 1, and I am one of them myself. Some are unusually wonderful people. Some are more neurotic than average, or complete lunatics.

2 is obviously much rarer. Sometimes, 2 is formalized in a title, as in the “arahant” in Buddhism, which I roughly understand as designating someone who is never superfluously an asshole, ever. People whose opinion I trust have told me that there are maybe a few of these people alive at any given time, like under ten. I know a few elder teachers who I’d guess are approaching the zip code.

From this perspective, I’m in favor of 2 being the goal, and 1 being considered a laudable credential, like a PhD, that prepares you to do serious work. If you have experienced the abundant joy and ease of the separate self departing, and you’re not actively concerned about how to give your gifts away—in whatever way that means for you personally—I’m really confused by your priorities.

I think sometimes people downplay the idea of working towards unusual moral perfection because the idea can invite neuroticism. But this is, as the kids say, a skill issue. We can all acknowledge that it’s possible to be much more loving, kind, skillful, patient, wise, etc, than we are, and that there are concrete steps we can take in this direction, without constantly chastising ourselves or being dishonest about our remaining flaws. We can also acknowledge that we can be much better without opting into all of the trappings of what exactly that means in a renunciate religious context. (I like Chapman’s nobility.)

1 makes 2 more possible, in my experience, by making it more painful when you’re an asshole. The freedom of the spiritual path is a freedom from the desire to do massive amounts of self-interested clinging. However, sometimes people become dharma teachers, accumulate acolytes who fawn over them, and cut off the possibility of receiving real feedback, and stagnate or worse.

Anything can be a defense against any other thing

Sometimes, people who notice how their minds work start thinking: “Aha! Thoughts are so tricky and elusive! As long as I’m staying with my embodied emotions, I won’t deceive myself.” Alas, the ego is tremendously good at avoiding things, and can use anything as a defense against any other thing. You can use a thought to defend yourself against an emotion, or an emotion as a defense against a thought. Or an emotion as a defense against another emotion. Or you can put an emotion outside, into the world, as a defense against feeling something inside (projection.) Etc etc etc.

Thus, woe unto the meditator who believes that the key to awakening is “embodiment” or “emotional release” or “attunement” or “samadhi” or “memory reconsolidation” any specific state or attribute or benefit. Sure, these are nice precursors, and accessing them will likely be part of the trip. Memory reconsolidation, specifically, can clear up everyday cognition to a shocking extent. But the trip isn’t about any of that specifically — it’s finally about something so terrifyingly simple that you don’t want to see it. Extended periods of samadhi will make it likelier that you see it, but not if you fetishize concentration. The thing you’re looking for is part of every state, but it transcends all of them.

And any state can be used to avoid awakening. And you will avoid awakening, because it is terrifying to the ego structure. That is part of the journey—the terror, and the resistance. The resistance that tends to naturally decrease as you get increasingly sick of your own shit, and thus desirous of an alternative.

The switchback

There is a really weird property to the meditation arc. It is unlike anything else I know of in skill acquisition.

Let’s decompose the meditation path into two steps.

1. Get really good at skilled state cultivation. Really relax for the first time in your life. Develop equanimity, fill yourself with bliss, absorb the cosmic pain and transmute it into pure love, tune into spaciousness. Wow yourself with how psychedelic experience can become. Maybe get some fun side benefits, like telepathy-level empathy, or a reduced need for sleep. Do self-inquiry until self/other duality falls away.

2. Radically let go of thinking that states are important at all. Let the spirit do whatever it wants with you. (You might notice that you were always doing this, you just didn’t know it.) Give up on getting anything from the meditative path except your completely normal life. Accept death completely.

Notice how weird this is? It’s a complete reversal! In an interview with Michael Taft, Tucker Peck analogized this movement to how a musician starts out playing scales, but graduates to “just feel the music, man.” This comparison is helpful, but it’s weirder than that. It’s as if becoming a great racer, at some point, involved getting out of your car and joining someone else’s pit crew.

I don’t imagine that there’s an exact recipe for deciding when it’s time to make the switch. Some people quite quickly acquire the insight necessary to understand what letting go actually means, and the resources necessary to do it. Some people, like me, take a much longer period of time.

For me, it was a somewhat disturbing change in direction—I was really indignant that no particular state held the key, that there was nothing I could do, but simply let go until the letting go worked its way through my entire bodymind, as my life fell into alignment with the path (or vice versa). The phrase “nothing needs to be done” was deeply upsetting to me, and deeply moving. I held it as a mantra in all of my waking hours.

This is also where it helped, personally, to be unafraid of the G-word, which is to say, God. It was helpful to take the perspective that none of my spiritual path was my work at all—this made it easier to allow the remaining work to do itself.

The waiting room

Anyway, related to the switchback: after the stage when it mostly becomes about letting go, many meditators arrive at an odd time in practice before the self-making engine is unmade. In this phase, there’s a high level of meditative skill, and a lot of insight, but it’s not clear where to go next. Like: self/other duality is nearly gone, there is a fairly relaxed sense of doership, emotional experience is high-definition. But you know you still haven’t experienced the Great Unmaking. You maybe try and talk yourself into thinking you’ve got it. But then you chat with people who have been through it, and there’s something in their eyes, like the quality of someone haunted by war, but the opposite of that. And you know you aren’t quite on their wavelength yet.

What to do then? The traditional advice is to simply do a bunch of shikantaza and wait for the thing to unmake itself. Or to go on retreat and get your concentration revved up. But I was rewarded by a different approach. I started assuming that the sense of self was hanging on for a logical reason, and I started to ask terrifying questions about that reason.

Questions like:

• Hey, have you ever managed to successfully avoid suffering for even one day? Really, if you’re being honest with yourself?

• What is your worst motivation for spiritual practice, and what if you will always have corrupt motivations like this?

• What if you still don’t understand the basic nature of suffering?

• What are you hoping spirituality will let you get away with?

• What part of your identity depends on being a spiritual person, or someone who is seeking?

• What if you got absolutely nothing from the spiritual search?

These questions surfaced psychological resistance to work with directly.

Obviously this is not the only approach. One person told me he got out of the waiting room by simply hearing and really trying to understand the phrase “you are trying too hard.”

At this stage, the path itself is often used as a defense against letting go.

Sexuality is an under-discussed piece of the puzzle

Assuming that the whole of the path is habituation to openness, to paraphrase Andrew Holecek. Like being open to what is, and dropping all of your resistance to what is going on. For many people, “resistance to what is going on” will include some number of sexual hangups. This can include being ashamed of one’s sexuality, shame around prior sexual experiences, excessive attachment to the idea of sexual conquest or one’s attractiveness, and many many others.

To put it another way, disembodiment is an intelligent strategy if you have some automatic rejection of sexual energies, urges, and associated feelings. Those are a substantial component of embodied experience! Being in presence is threatening if your sexuality is even a little bit alive and you’re not okay with it.

I’ve found it extremely powerful to simply work with sexual hangups and feelings the way I would work with anything else. Like: greeting sexuality with more equanimity, treating sexual feelings as doorways to jhanic states, bringing open loving awareness to sexual shame, et cetera.

Many meditators don’t talk about how powerful and important this can be. There are three reasons, I think:

1. Sex is awkward and taboo to begin with, and there are some Buddhist cultural hangups in the meditation world.

2. If you introduce sexual stuff to your meditation group, it’s easy to accidentally do a sex cult. On the 1:1 level, introducing sexuality into a teaching relationship requires care, and many teachers, reasonably, do not want to go there.

3. Few of us want to be confused with the neo-tantra nerds, for whom sexuality is a Special Interest, who always have horny energy. I happen to like a lot of these people, but they are not normal, and thus not aspirational for many meditators.

And so, the possibility of bringing sexuality into practice is under-discussed (in some circles). But if you don’t want to be a monastic and go for the “shut it off” option, you are going to have to work with your sexuality. Which simply means trying to experience it without resistance, and also trying to incorporate it into an ethical life, as a vessel for connection, and a set of energies that bring us into contact with creation. (May I suggest marriage as a spiritual practice?)

What the happiness without conditions means

I’d always misread the phrase “the happiness without conditions.” I took it to mean a kind of happiness that persists no matter what life throws at you. I have come to a different conclusion. It refers to the happiness that arises if, and only if, you stop putting conditions on life.

Future essays to come, maybe, on request:

• The shocking power of the Diamond Sutra

• Non-dual glimpse practice as Legend of Zelda map destination

• Some species of energy shit I’ve seen out there

Photo credit goes to Daido Moriyama.

Meditation is about more than one thing. But if it were just about one thing, it would be releasing mental tension so you can fully feel your experience. All of the fancy insights you are trying to get from meditation become nakedly obvious, in due time, once you drop inhibitions to feeling what is already going on. The same insights are available at the office or the monastery, when you allow yourself to see them.

You might be like: but what about distraction, aren’t I supposed to be staying focused? Yes. Continuity of attention is good. Enough continuity will likely rocket you into some wonderful bliss state, if that’s what you’re into. And the distraction that keeps you from establishing this is typically an automatic flinch. Relax all the flinching and you will find progressively expanding stillness, which you can point in some direction if you want to. The quality of a mind that is not being messed with constantly is tranquil, assuming that basic survival is taken care of.

There are sources of mental tension that meditators often don’t notice because they are simply accepted as background activities/properties of the mind. It’s not clear, until you learn to turn them off, that they are optional. But they are optional, and toggling them off is necessary to experience the profound depths of practice.

This is not a “meditation 101” post. For that, go here.

Tracking/predicting experience, rather than being open to possibility

We have an automatic tendency to monitor ongoing experience and predict the next moment. Mentally, this creates a sense of wariness or watchfulness, which is a layer of tension. Also, it becomes a self-fulfilling prophecy: the mental intention to predict experience keeps experience predictable by reducing your sensitivity to variation.

Helpful tricks:

• Notice if there’s a moment of relaxation, or a pause in mental activity, after you think “I don’t know what will happen next,” or “I can’t predict experience.” See if you can ease into that pause.

• Notice how there is constant detail in sensory experience that you can’t predict. The next thought, the next flicker of body sensation, the next shade of emotion. Relax into the flow, allow yourself to be drawn in by the unpredictable flux of subtlety.

• See if you can let the breath drive itself, by responding naturally to the desire for oxygen rather than trying to keep your breath predictable, while maintaining mindfulness.

Reaching out and grabbing experience, rather than receiving experience

There is an unconscious tendency to direct attention to specific portions of experience—to mentally “squint” at what we’re looking at, for example. This is not actually necessary for perception. In meditation, it is typically more helpful to enter a mode of holistic, receptive experiencing, where we let the field of experience come to us.

Helpful tricks:

• Play with the prompt “I am a puddle, and experience is the rain.” (Thanks to Hormeze for the inspiration.)

• Notice that you are already listening without the decision to listen. See if you can do this with all of your senses.

• Allow your awareness to be broad and inclusive: lightly include both your head and your feet in experience. A wide aperture of awareness naturally creates a receptive mode.

Having a frantic pace of intending

Many intentions function best when held lightly. For example, when you’re walking to a destination, you typically don’t need to remind yourself to keep walking every few feet—you only need to remind yourself if you get distracted by something and stop walking. The intentional savoring required by focused meditation practice (like jhana practice, for example) is one of these intentions best held lightly: it is a direction we allow ourselves to move in. However, many novice meditators engage in the frantic renewal of intention, reminding themselves constantly of what they ought to be doing. Not helpful!

Helpful tricks:

• Reduce the pace and intensity of voluntary mental action. If the mind is chaotic in the short term, trust that this will settle down as you relax into pleasant feelings.

• Do the unhelpful thing intentionally, so you can get a feel for the helpful thing. Frantically issue a few mental commands to yourself—voluntarily engage yourself in thought repeatedly at a fast pace. Notice the turbulence this creates. Then, try to do the opposite: see if you can smoothly, slowly connect with one mental intention.

• Try, for a period, to completely let go of voluntary mental action. See what it’s like to have faith that the mind can settle itself, if you don’t shake it. (This may take some minutes, and may not happen if mental activity is particularly intense. It is also a whole style of meditation.)

Evaluating whether or not certain things are supposed to be happening in meditation

Mental movements that get in the way of absorption, sometimes called “hindrances”— like doubting your meditative skill, other discursive thought, restlessness—always occur in meditation, even to very experienced practitioners. Experience gives you the capacity to work with these mental events, it doesn’t banish them. So, generally, the most helpful attitude is one of “allow, then reprioritize”: don’t get disturbed by the mental event, just notice it and shift back to the intention of meditation. But many novice meditators instead stiffen up, tightening too intensely around the intention to keep mental activity restricted, in a way that is counterproductive.

Helpful tricks:

• Internally affirm “everything is allowed, everything can be interesting.” Detours can be fun parts of the trip.

• Check to make sure you’re not enforcing overly harsh extensions of general principles. For example, notice whether you’re interpreting “try not to intentionally get caught up in thought” as “never have or get caught up in thoughts.” If you are, stop it.

• See if you can hold the mental intention to meditate a bit more loosely. To get a feel for loosening intention, imagine throwing a ball at a specific target, and then imagine loosely chucking it in a direction.

• For a few minutes, drop all control. Allow random distraction while loosely noticing it, as if you’re a voyeur dropping in on your thoughts and feelings. Try to enjoy the randomness, the unpredictable nature of interior life. Then return to a loosely held intention.

Guarding against emotional intensity

Often, people are taught to emotionally contain themselves at a young age, and the most robust way to contain yourself is to not allow yourself to feel too intensely. This is adaptive in development, but unnecessary for adults with good emotional regulation. And yet the habit to constrain your emotional experience often remains present in adult meditators. It adds tension and drains the color from meditation and life.

Helpful tricks:

• Just ask: could I let myself feel everything 10% more? If that worked, what about 20% more?

• Check whether there’s a perceived boundary between you and the emotion in your experience, a sense that there’s a spatial “partition” in the way of feeling. If so, see if you can earnestly adopt the intention to relax that boundary.

• If your experience feels “dull” or “boring” or “unemotional,” what does that feel like? What is the texture? If the experience isn’t peaceful, there is probably some subtle anger, sadness, or fear in it that will intensify if you tune in. (And in the context of meditation, that is a good thing, assuming you’re in your window of tolerance.)

Tracking time, tracking space

Space and time—by which I mean, the sense of where on earth you are, and what time it is—aren’t directly created by bare sense experience, they are inferences placed on top. When you look at a sunset and you are absorbed in it, no part of the experience unambiguously tells you “it’s 6:22 PM.” Temporarily relaxing the tracking of space and time can create incredible experiences in meditation. Reflect on how flow states are typically characterized by dropping these frames of reference: wouldn’t it be nice to gain the ability to temporarily drop the frame?

Helpful tricks:

• Ask: what mental sensations, specifically, tell me that I’m located in this place, or this time? Once you notice that the feelings of space and time are being created by a mental process of “marking” or “tracking” reality, the tracking often diminishes all by itself.

• Play with the question: “what if there is only one eternal moment?” Or: “what if everything in my life has happened within one space of awareness?” The intention is not to entertain these as philosophical or intellectual truths, but to use them as temporary lenses on experience.

• Ask yourself whether there is a quality of awareness that is ageless, a quality has been the same since you were a child. See if you can tune into this foundational quality. Remembering spacious, expansive-feeling moments from childhood may help as a reference.

Problem: The essence of the dharma is not grasping, and doing some other nicer stuff instead. You know, the noble truths that we keep talking about. But, in speaking about all the nuances therein, and building a religion, the teaching has gotten all tangled up.

Solution: Let’s make a tradition built around less theorizing, and more interfacing with a master who serves as an embodiment of the teaching. Just sit there and let go, and have the master trigger you when you’re missing the point.

New side effects: Some people need all the theorizing to understand what’s going on. Also, just sitting there and intermittently getting triggered is an abrasive style for many. So, a few students get traumatized, and a bunch of others don’t get it, and occasionally your teacher is just a lunatic.

We can also think this way about valuable modern wisdom teaching. Let’s take my understanding of Art of Accomplishment (hey AoA friends!).

Problem: Much of the beauty of the contemplative path is in working with emotion. But people use the contemplative path as another way to resist emotion, despite what everyone says in all the books—and for strivey people, holding in emotion is perhaps the most common form of grasping.

Solution: Let’s go for that juicy emotional release right away, and use that release to train people on what it feels like to unclench themselves, with the wonderful feedback loop of connection.

New side effects: Focusing on your emotions and connection can just become a new kind of grasping. Some people who might need better self-regulation skills become less functional as they over-focus on chasing catharsis.

Or Jhourney, an organization which I love, and happily collaborate with (hello Jhourney colleagues!).

Problem: People miss out on the life-changing effects of meditation because they don’t know that some helpful and beautiful states might be closer than they think, and they’ll maybe never undertake the experimentation required to hit them.

Solution: Let’s make a retreat that gives people agency to experiment in such a way that they hit an onramp to unbelievable pleasure and release, much faster than usual.

New side effects: There is no way to do this that won’t create, in some people, strivey button-mashing, reinforcing the attitude of “optimize myself harder.” Occasionally someone will hit an emotional sinkhole, and bliss practice will suddenly be therapy practice (productive, even amazing, but less fun).

Or, for more lightning round, Byron Katie’s work.

Problem: People get caught up with thoughts to try to make themselves happy, when, often, deconstructing thought is the most immediate path to mental freedom.

Solution: Here’s a powerful tool for creating mental fluidity, a rapid procedure for loosening the grip of painful identity beliefs.

New side effects: People get all caught up on the tool of debugging their reactive thinking, thus becoming more worried about thoughts, rather than understanding mental fluidity as a pointer towards a non-graspy way of relating to life.

I have fun criticizing different traditions and teachings from this standpoint, noticing all the ways they break down in implementation. However, for a long time, this criticism carried the assumption that someday, I’d come up with a better, pithier instruction set that would avoid these side effects.

And then I noticed that years after writing a passionate post called Deep Okayness, about the positive effects of working lovingly with all the difficult parts of your psychology, people still came up to me saying: “hey, how do I know I’ve reached real Deep Okayness? I keep feeling bad about myself because I haven’t done self-acceptance right.” Sometimes they assume I will personally disapprove of them for this, which makes me sad. I now have a Deep Understandingness of how any pointer you give someone can become fuel for more grasping.

More recently, I started to wonder: wait. What if I’m thinking about all of this the wrong way? What if this is the spiritual path?

Problem: Life. Seems bad? Feels bad? Some wise-seeming people say it’s actually good? What do.

The spiritual path: Open up, try to be kind, notice how wonderful the universe is, let this fill you with awe and humility, notice that there’s plenty of work to be done, especially on yourself. Here are a million practices and frameworks that might help.

Side effect: Whatever fucked up way you relate to the above instructions, or the teachers who convey them, or a cool spiritual experience you have, will cause you to become further ensnarled in your suffering.

Which is also the solution: Eventually you will be forced to stop doing whatever stupid shit the spiritual path caused you to do. Hopefully a kind teacher (formal or informal) will be there to point out the stupid shit. Someday, letting go will show itself, by the grace of God, and you will be transformed. Hopefully you can also remain honest about your flaws.

A vessel for transformation is an opportunity to come up against your foibles. They are the same thing.

Or: you come to God by struggling with God.

This has given me a sense of reality about what we’re all doing here. None of us can spread, reinterpret, or revamp these precious teachings in a way that avoids causing temporary damage. Temporary damage is the nature of the work—hopefully, damage that causes helpful adaptation, which is to say, wisdom. All we can do is be kind, be honest, be pragmatic, and try to exemplify wisdom ourselves in the way we relate to people, such that a crude attempt to copy us will result in the least harmful errors. An opportunity to refine this craft is there in every interaction.

If the wisdom is there, then people will feel better, on average, and move slightly closer to liberation as a result of having interacted with us. If we lose track of the wisdom, we will know it also by the direct effects of our mode of relating. None of us can know the ultimate benefit. That is a matter of faith.

I try to remember my favorite words of the Diamond Sutra. “In the realm of complete nirvana, I shall liberate all beings. And while I thus liberate beings, not a single being is liberated.” For me, this is a rich paradox with many implications. One is a pointer for how to be with people: the moment that I’m splitting the world into you, the un-free thing, and me, the thing trying to free you, I have already lost the plot. It is so easy to slip out of actual relation, back into a place of superiority or technique, and forget the nature of what we’re doing here.

May we all keep our heads out of our asses, and remember!

There are two kinds of desire. It’s hard to tease them apart conceptually. But that doesn’t matter too much, because it’s relatively easy to tell them apart experientially. They are tanha, and chanda.

Tanha: Scarcity-based desire. Graspy, clingy. Feels like fighting life. “I don’t want this headache, let me tense my forehead until it goes away.” Perhaps if I get a little more social status, I will finally love myself. Sigh, I don’t really want to do the dishes, but I should, because I want more sex and less arguments. Though I’m full-to-bursting, I’m taking another bite of ice cream. Push motivation.

Chanda: Whole-being desire. The kind of desire you fall into, which requires energy to resist. Your arm is being pulled by the paintbrush. The hours-long conversation that feels like it’s over in five minutes. Getting lost in a book. Slowly teasing apart a really gratifying puzzle. Desire that refreshes you when indulged, rather than leaving you feeling spent and dirty. Pull motivation.

The most interesting finding in human psychology, ever, is that basically all of us are born with the wrong intuition about how to be happy. We think that doing enough tanha, enough grabbing, will please us. But actually, grabbing is the source of something like 90% of our unhappiness. It’s a basically dissociative reaction to reality which creates a sense of temporary dissatisfaction, like putting on tight shoes so that later your feet will feel good again. Skip it altogether, as much as possible, if you want to be at peace. It’s crazy how true, and how unintuitive, this is. (The main reason long-term meditation makes people wildly happy is that it sensitizes you to when you’re doing tanha, thus providing the opportunity to relax most of it, which does beautiful things to the mind.)

We also tend towards poor intuitions about chanda. Perhaps we say to ourselves: “my intuition is telling me that I need to become a CEO to be happy.” But it would be weird if that were the case, because the intuition mechanisms in your mind are much older than job titles. What’s likelier is that there are certain configurations of experience that will make you happy. Like “leading a group of people,” or “slowly turning something over in your mind,” or “transmuting reality into an artistic representation.”

For example, I’ve noticed that I’m persistently delighted by affecting someone directly, in a 1:1 relationship. This can be accomplished by writing someone an email, or doing coaching, or cooking someone a meal. If I get creative about where to find this particular chanda, it is all over the place.

The things that satisfy you most will contain multiple compulsive delights. For example, I loved being a bartender, because it contained the opportunity to affect someone directly, and the opportunity to appreciate aesthetic experience, and useful low-resistance exercise, three personal sources of chanda. This made nearly every shift feel like an engaging dance, rather than a boring slog. To someone unaffected by such delights, it would be a horrible job.

Chanda is not particularly negotiable. As in: what provides it for you changes slowly over a lifetime, and the change is not voluntary. This is weird, because a shocking amount of human psychology is negotiable. You can reprogram disgust reactions that cause you to be racist or regard avocados as poison. People who are scared of heights can become mountaineers. Dissociated nerds can become sexual athlete tango champions. You can forgive people who have wounded you unforgivably. It is incredible how plastic we are.

But the energy patterns that give us compulsive delight? Mostly static, and mostly not in our control.

This implies how you can figure out your chanda, if you don’t know what it is. Look for the repeating patterns of desire in moments when you are truly happy. Look for the arrangements of energy that compel you. Remember, you are looking for general shapes, like “the feeling of sharing confidences,” or “the knowledge that you have served your duty.” Language here only serves as a pointer to the elemental arrangements of experience.

Meanwhile, tanha is much more variable, because the mind can create diverse feelings of scarcity. You might have a grippy desire to be skinnier if hanging around glamorously slender people, and then, later on, a grippy desire to be more muscular if you hang out with a bunch of gym rats. Around wealthy acquaintances, you might acquire a temporary itchiness about your financial status, and then later, traveling in a poor country, a shameful urge to conceal your wealth.

So your true desires will show up repeatedly in different guises, unmistakable signatures signed in different colors. Whereas your insecurity-based wants will likely be more environment-specific.

Obviously the separation isn’t completely clean. Designing a fashion line might involve chanda around the creative act, and then tanha around clingily fixating on whether certain colleagues show up to the runway show. But also obviously, some acts have a more favorable ratio.

This is a way more helpful distinction than extrinsic vs. intrinsic, a division that makes no fucking sense if you think about it for more than two seconds, since most of our feelings occur in the context of relationship.

This is the important thing:

The people I know who are happiest, most productive, and most creative are people who feed off chanda. They have structured their lives such that their work, relationships, and pastimes repeatedly offer true delight, in ways that also have prosocial externalities. This applies to artists, founders, chefs, housewives, all kinds of people. To me, a wonderful example is Tyler Cowen, who has said he lives selfishly, in complete surrender to his interests, but who gives out tons of money to promising young people, produces a huge amount of insightful writing for free, and so on. Structuring your life in this way requires creativity and flexibility about how to get your chanda, rather than attachment to a specific concept of what your job/relationships/hobbies ought to be.

Does all of this mean that we should never do tanha? Probably that is an overreaction. Sometimes there are chores that won’t be accomplished if we insist on enjoying them. And sometimes there are tradeoffs that totally make sense—like pushing yourself really hard to temporarily do a gig that gives you life-changing money or status, thus opening up future options for life engineering. Occasionally, being moral might require doing some gripping, like, say, holding yourself back from having an affair if you’re in an unhappy marriage with resolvable issues. Also, basically nobody writes a good book without some tanha. “Just follow your bliss” is a good corrective principle for strivers, but infantile if taken as sufficient guidance period.

So a rough guideline presents itself: engage in tanha if it helps set you up for more chanda in your future, or it’s a really good way to increase the welfare of others in some situation. Otherwise, think twice. Filling your days with tanha will lead to a tense face, a writhing gut, and a false life.

If you can engineer a life that’s at least benign for other people that’s mostly chanda, you are doing well. And if you can design a life where getting your chanda is also good for others, you are insanely fortunate. Most materially wealthy people live in a prison, compared to the freedom you enjoy. Be completely grateful that you and the world can operate in joyful harmony.

This post was a crystallization of some thoughts that have been percolating for awhile, but the crystallization was directly prompted by this great Tyler Alterman post: “Chanda is desire that arises from a place of non-tension. It often feels like a relaxed current, but can sometime be strong, channeled, like a great benevolent wave surging outward – and yet it is unattached to outcome. Intensify this style of desire while releasing craving & clinging, and genius springs naturally.” Photo credit goes to Daido Moriyama.

Recently, I’ve been getting the urge to send the following message to everyone I care about: if I die soon, know I was happy and that I love you.

I don’t plan to die, that’s not what brought this on. Although I’m going to Mexico soon, and international travel always gives me a little paranoia, even though I know the statistics are i…

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She saw herself as someone ambushed by life. Her hopes and dreams were being withheld from her—nothing she could do would bring them closer. And any nearby substitute prizes were deemed unworthy. At times, she regarded me as the only person who could help, and her ongoing unhappiness was also evidence of my inadequacy. This was hallucinatory because she had a lot of real power, which she was disregarding.

Meanwhile, I did see myself as a helper, who could make her happy. When my interventions failed to produce the desired result, I became resentful. She just wouldn’t accept my assistance, that’s why she was miserable. This was hallucinatory because I had very little ability to fix what was wrong. I couldn’t control her. Meanwhile, I was overlooking my own conspicuous issues.

This wasn’t the entirety of the relationship, but it was a lot of it. Later, after I exited the relationship and regained consciousness, I realized: oh, I am a therapeutic cliche. This is the drama triangle, right? We were in the drama triangle. Later, we reconciled, and we both talked about this dynamic as if we’d been drunk the whole time—neither of us recognized the realities which were so convincing previously.

Here is the way I now understand the Karpman drama triangle, which is a therapeutic cliche that captures an important element of social reality.

Let’s say life is giving you information you can learn from. Events tell you that you should update a behavioral pattern, or admit your complicity in your ongoing pain, or let other people be the way they are, or something humiliating like that. But you don’t want to learn! That would be embarrassing and hard! Instead, you want to slip into a cartoon universe where there are three roles. Each role contains a psychological defense—it shields you from pain, and provides motivation (to act immaturely) where you might otherwise feel helpless.

Here are the basic scripts:

The victim: Everything is being done to me. I have no agency or responsibility in the present—maybe I did once, but I squandered it. Someone needs to rescue me. (The goal of the victim is to avoid the scariness of responsibility, and embarrassment around being a contributor to the situation.)

The rescuer: This person is hopeless. It’s up to me to help them. If they refuse my help, or implement my advice imperfectly, that just goes to show how much help they need. (The goal of the rescuer is to avoid their own feelings of helplessness, and any other inconvenient circumstances they’re dealing with, in favor of manufacturing a feeling of goodness or usefulness.)

The persecutor: This person is wrong. It is my righteous duty to inflict retribution, or at the very least to tell them exactly why they were wrong, so they can feel shame, and order will be restored to the universe. (The goal of the persecutor is to salvage the feeling of righteousness from the unbearable pain and ambiguity of life.)

My astute friend Milan Cvitkovic notes this maps onto three of the four reactions to overwhelm: fight, freeze, and fawn. The fourth, flight, is represented by the tactic “leave the situation immediately,” which does cause drama, just in your absence.

Drama triangle 101 is to simply know that these are three common hallucinations for human beings to slip into, and, moreover, that when you’re in one of these hallucinations, you will be seized by a feeling of conviction. You’ll have the delicious sense that you’re finally gripping the situation, you know how to advance to the next stage of the game. This false certainty helps you avoid whatever the hallucination is designed to conceal. Typically, this pseudo-certainty bears a frenetic quality, which is palpably different from the stillness of true insight. Watch for defensiveness: a flashing irritability that might come up when you’re questioned about the conclusions you’ve come to.

Each of us has a favorite role we tend to slip into. Given the above sketch, it should be obvious that rescuer is my favorite. Which sounds nice, until you consider the fucked up part: that it means I’m liable to subconsciously locate ways in which other people are incapable, so I can feel better about myself. Ironically, to get good at helping people, I had to get over this compulsive rescuer dynamic.

You might respond—is it always bad to be a rescuer? Can’t you actually kind of rescue people sometimes? Yes, absolutely. There are also real victims, and it is good sometimes to prosecute. One interesting thing about these three roles is that they are each cousin to skillful action:

• If you’re a victim of harm, it’s good to notice this, grieve if required, and sometimes recruit others to help. Just not at the cost of discarding your responsibility in shaping situations, or your own power to work with all the cards you’re dealt.

• It’s good to assist others. Reality is a team sport. But you can’t control anybody else, or make them well by force, and maybe they don’t agree with your definition of wellness. Skilled assistance is empathetic, humble, and situation-specific.

• Sometimes there really are wrongs to be addressed. But what would actually be just or helpful is rarely depicted accurately by your immediate desire for moral or personal satisfaction.

So, if you find yourself believing one of these roles, it might not be 100% fiction. It’s more likely that it’s just an exaggeration. Getting to a nuanced perspective probably requires admitting emotions and thoughts that might be unflattering to the current perspective. This is desirable, because a dramatic reaction tends to create more drama rather than resolving the underlying pain.

Here is a suitably embarrassing example of this. Early on in my marriage, it was my birthday, and my wife was bad at celebrating it, because I hadn’t specified what I wanted adequately. We were sitting in the car, and I was feeling disappointed at how the day was going. I saw a chain of thoughts forming in front of me—about how she clearly misunderstood me, and, moreover, I’d gotten into another relationship with someone who didn’t care about my preferences. Clearly, my role in life, I realized, was to be the giver, not the receiver. Could I put up with pain like that? Did I have the strength?

And then I noticed this long line of thoughts stretching out from my forehead and thought, oh. This is the victim role being offered to me, to cover up my discomfort. My brain has given me this mask, all ready to put on. But it’s not real. My birthday is sucking right now because I’m uncomfortable with spelling out exactly what I want. I took a deep breath, and said exactly what I wanted, and my wife gave that to me. The whole cartoon universe melted.

That’s drama triangle 101: notice the hallucination, hopefully before you put it into practice. See if you can embrace the discomfort underneath, and stop pulling other people into choreographed conflicts.

As for when other people bring you drama, I don’t have the perfect recipe. Sometimes, a civilized response can end drama instantly—like listening patiently to someone who brings you a grievance, rather than responding defensively. Sometimes, if faced with a dramatist of higher intensity, you’ll need to grey rock or withdraw, simply removing your oxygen from the fire. And with very intense drama, removing your personal oxygen might not end the situation, because other people can get drawn in.

That being the 101, what is the 201?

Earthquake people

Have you ever had a relationship with somebody else that felt really spicy? Like in a destabilizing way, not in a fun way?

Maybe when you entered their life, they introduced an incandescent quality. Everything began glowing. They instantly declared you a favorite person. Then, like a summer storm, a sudden turn occurred. There was this situation they needed help with. Something with a landlord, or a partner — an enemy for you to ally against. Pulled into this situation abruptly, you couldn’t totally meet the requirements foisted upon you. And then, suddenly, you found yourself on the outside, declared an enemy. Then, weeks later, a peace offering, luring you back in.

Or maybe it just felt really easy for things to get into a bad place. Everything was fine in the relationship for days, maybe even weeks at a time. And then you crossed a threshold you didn’t see coming, and your behavior was suddenly deemed unacceptable. Wham! Suddenly, you became a villain, or you were drafted into service as a rescuer, to mend your supposed harms. After a few days, back to uneasy tranquility, and then repeat.

Some people have an inherent talent for grabbing onto others by pulling them into drama. All it takes is an inflammatory text message, or a sudden outburst. And, because each drama can only be dragged out so long, after you reach equilibrium, they soon start another chapter. People can do this by pulling you into a different role, or simply by spamming you with the same role repeatedly—like putting themselves in the victim or persecutor role by presenting grievance after grievance. Advanced players can change the scale of the drama by pulling in other players, or moving to a different stage—like by taking a dispute public over social media.

There’s a natural question here, with personal and societal implications—how many such people are there? And what are the different kinds of dramatists? We find potential answers in an intriguing psychology textbook, Demystifying Personality Disorders, by Gregory W. Lester, Ph.D. and Alan Godwin, Psy.D.

The textbook’s POV, supposedly crafted based on thousands of clinical evaluations, is that some portion of humanity is chronically resistant to feedback, and thus, routinely creates drama so as not to learn from their behavior. It labels this an essential component of a disordered personality, and thus characterizes personality disorders in a novel way—via different patterns of drama triangle activity. We call these patterns things like “borderline” and “schizoid,” but they’re just different patterns—many of which respond well to therapeutic intervention, some not so much.

Obviously, this isn’t “truer” than other systems of diagnosis, but it’s a provocative lens. According to the textbook, a fairly large percentage of the population is walking around with one of these disorders: 15-19%. I don’t know enough to evaluate this claim. But…

The political aspect (quite speculative)

Here is an unoriginal insight: politics looks similar at extremes. It’s clear that people understand this based on the very fact that the term “woke right” exists. At both far ends of the political spectrum, we find cartoonish worldviews, characterized by a sense of opposition and grievance: heroes and villains, a zero-sum game that someone else is winning. Without the Jews everything would be fine. Or the wealthy. Or the white cismale. Or the transgenders. And on and on.

If we tentatively accept the conclusion that something like 15% of the population is walking around with a drama triangle view of the world, this starts to seem like the natural order, which might be depressingly difficult to reverse. There is a portion of humanity tragically stuck in repetitive, simplistic characterizations of their lives. This simplicity propagates to their views about the world as a whole. They perceive everything as drama. And this contingent is large, so, in a two-party country, any political faction that refuses to cater to that perception will lose.

The drama triangle lens also makes new meaning of temporary moments of political craziness, like the height of woke, or the War on Terror: we’re all vulnerable to transient trips through the drama triangle. Most of us snap out of it eventually. Some don’t, just picking new rescuers, persecutors, and victims, forever.

The mind control aspect (less speculative)

I’ve noticed that most adults, including me, basically don’t have a drama-based view of their life—no perpetual victim mindset, or savior complex, or whatever. However, they don’t necessarily possess this sophistication about narratives passing through their world. Or narratives they manufacture.

In one of Ryan Lizza’s recent articles, he makes passing mention of “…Donald Trump, who turned everything in his life into an easily digestible story in which he was a hero or victim under attack by vindictive heels.” And I instantly thought: oh yes, that’s a huge part of his cleverness. Drama is mimetically fit; you can throw it onto any situation and make it instantly memorable. Reacting to a dramatic storyline gets you engaged, if you respond with anything other than a flat dismissal of the frame.

How many times have you been consoling a friend after a breakup, and found yourself eager to condemn their ex as a monster, absolving your friend of all responsibility—perhaps in response to an implicit demand that you do this? How many times have you sought sympathy by complaining about a superior or colleague, while failing to mention your clear responsibility in setting up the situation? How many times have you posted about some injustice or bad behavior online, inviting others to join you in condemnation, while privately suspecting the situation might be more ambiguous than your post suggests?

It’s common and perfectly rational behavior: we flatten a situation in order to pull others into a choreographed response, or join a choreography in motion. We create hallucinations to pull others into, even if we, ourselves, understand the complexity of the underlying situation.

Very few of us are completely free of drama.

Thank you to Cate Hall, Carly Valancy, and Stephen Zerfas for notes on this piece.

Psychotherapy and traditional Buddhist meditation both offer compelling ideas of how to live a healthy life, ideas which happen to be completely incompatible.

The Buddhist idea is that your suffering is caused by an illusory sense of identity that separates you from experience. To dissolve this illusory self, inquire into the substance of your thoughts and emotions rather than getting caught in them, notice that they are transient, and, eventually, your illusory identity will dissolve. Your stories are not important.

The psychotherapeutic idea is that your identity is a densely woven fabric informed by all of your experiences, which contains valuable truths, but also outdated coping strategies. To become healthier, unweave and reweave this patterning, by carefully examining your stories and emotions, considering them important clues about how you function.

You can see the incompatibility here. One perspective regards mental content as important, and the primary material to work with. The other regards mental content as waves, which, instead of getting caught in, we should learn to simply surf.

Most people who have tried to work with both of these theories have noticed that they both work sometimes, despite being philosophically incompatible. So what is the synthesis of these perspectives?

It is something like: meditation can make you a really good therapy patient. It can dissolve some thoughts and emotions that are merely the mental engine sputtering. And it can also fast-forward you to difficult content that requires therapeutic work. Addressing this content will improve your stillness of mind, which will make you a better meditator, forming a virtuous feedback loop. Over time, your ego gets thinner and more flexible. You have a more durable happiness, and more awareness of the effects of your behavior. If you follow this loop far enough, you can maybe become a saint in this lifetime (like, over the course of decades). Not in the sense of working miracles (although if that happens to you, cool) but more in the sense of being unusually dedicated and skillful in living a life that benefits others.

The sweet smell of coherence floods the pagoda. But how to actually practice the combination of meditation and therapy? The above is not a sufficient operating manual. Making the above paragraph into a practice would be like trying to derive a gym routine from the principle “work your muscles hard enough to hurt them temporarily, not permanently.”

Sanity and Sainthood is the closest thing to a sufficient operating manual on the market. It’s written by Dr. Tucker Peck, a clinical psychologist and dharma teacher, who has years of experience watching people run afoul of the intersection. He thus is equipped to make credible recommendations about when you should work on the content of your mind, as opposed to merely observing it with meditative equanimity. He’s also pithy, funny, and wise, and the book represents him well, so it’s fun to read even if you’re not totally gaga about meditation yet.

The biggest endorsement I can give this book is that I once considered writing a book like this, but now I consider the job done. I can write something else. Also, I would’ve been a lot less stupid in areas of my meditation practice if I’d been given this book when I was 20. (For this reason, I have extra copies of this book to opportunistically give to young meditators I meet.)

Readers of this blog will know that I’ve experienced transformative effects from long-term meditation, more than I believed possible. I’m still amazed by what my life has become, on a near-daily basis. But something I don’t emphasize enough, perhaps, is that I spent hundreds of hours bashing my head against meditation in my early 20s, practice hours that were net negative for my mental health. Largely, my early practice wasn’t helpful because I was trying not to have a psychology, something this book would’ve talked me out of.

There’s lots of solid practical advice in this book. But most readers of self-help will notice that the best books don’t really work by imparting advice. You might take some of the advice, but the real action of self-help is vibe transmission. By reading the best self-help, you absorb the mental presence of a wise person, who can serve as a virtual interlocutor. In this capacity, Tucker shines.

An indicative story about him: I went for a walk with Tucker during the really psychoactive part of my meditation practice. I told him that I was extremely happy. He said something mildly congratulatory, and then said something like, “consider that you’re a privileged, healthy, smart married person living one of the best lives in history. Maybe it’s just appropriate that you’re happy, and that’s nice or whatever, but you can shoot for something more than that.” He managed to say it so gently and matter-of-factly that I immediately realized that it was true, with no resistance. Tucker is one of those people who can collapse your bullshit quickly, but it feels like a big hug. It helps that he is also highly conscious of his own frailties—this book doubles as an atlas of Tucker’s neuroses, which are presented joyfully.

If I have a criticism of the book, it’s that it, perhaps, underrates the effects of long-term serious meditation. Reading this book, you might get the sense that long-term meditation will make you quite pleased, whereas my experience is that it can completely explode what you thought life was, and replace it with something immeasurably better.

But then again, maybe this kind of dissuasion is helpful. My experience with meditation started getting really good after about 12 on-and-off years of it, with many, many hours of psychological self-exploration that were not immediately pleasurable. I write a sentence like this in almost every one of my posts raving about the era of practice I’m in now, and yet somehow people don’t manage to read the part where I say it was hard, based on some of the emails I get. Like people mentally skip the part where I struggled with myself for an extended period. That’s a message that seems unabsorbable by seekers in an aspirational mood.

Some meditation books will tell you that you can count on enlightenment within a year or two of serious practice, which actually does happen to some lucky students, but not to like 95%. The more typical case is not as rosy. One of Tucker’s big points in this book is that meditation gives you the opportunity to look at, and mend, destructive parts of your psychology—and this means confronting your destructive psychology, which is not pleasant in the short-term. So taking up meditation, even when it goes quite well, can involve a significant dip in perceived happiness before the benefits start kicking in.

And even if meditation gives you dramatic results in the short term—say, if you have a spectacular time on a Jhourney retreat—it typically tends to take many hours to integrate this into your life, and actually live differently. As in other domains, dramatic results from self-work tend to result from unusual levels of dedication.

Meanwhile, Sanity and Sainthood is one of the few meditation books that doesn’t lie to you, at all. I wish it had a more clickbaity title, it would sell more copies. But it is the anti-clickbait meditation book, and for that, it should be praised.

Geese — Getting Killed 2/5. When I was an adolescent, people were really worried about “irony” in popular culture. I think this is what they were worried about. What happens if you make rock music and have a distaste for crude maleness, but don’t suggest anything solid as a replacement? What if you did Talking Heads, but took away the fear and wond…

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Next week, I’ll have a paywalled post of truly deep Enneagram nerdery, about the flaws I see in the system, how it compares to other diagnostics, and various other bits and bobs.

5: The sage, the knower, the hermit

Strengths: Curiosity, open-mindedness, competence through knowledge. The curators of entirely personal lifetime research projects, which sometimes yield marvelous feats of invention.

Weaknesses: Stinginess, isolation, overthinking. Slothful overwhelm. They’ll read several articles about historical landscaping design but find it too overwhelming to hire a gardener.

Core fear: Without your shield of knowledge, you will be overwhelmed by the unexpected. Better plan ahead so you never look stupid, ever. Your needs are too overwhelming for others, and vice versa, so you should keep your distance.

On the group hike of life, they’ve got a detailed map, tracking the location of minerals far underground, and weather systems originating far away. It gets them there, you just wonder how much they’re seeing what’s in front of them.

There is a fantasy that Enneagram 5s find appealing, almost universally. It is this: you are a wizard, and in your laboratory, there are grimoires containing powerful spells. If you spend enough time studying the grimoires, when you venture outside of the laboratory, you will be able to instantly vanquish all of life’s problems with your superior knowledge.

They are the most unusual type, as measured by sheer difference from others, even though they are not motivated by specialness in the same way 4s are. “Remote” is a word that comes to mind. The reason is that they instinctively want to search beyond the social consensus for knowledge. Not because they want to rebel, necessarily — they just know how fallible received wisdom is, and have a hunger to find out what is really going on. This also makes them reflexively search for the antithesis of their position. Think of the Christian scholar who is deeply aware of scriptural inconsistencies, or the libertarian who can enumerate the downsides of free market capitalism more ably than the average communist. What gives them great satisfaction is looking over a panorama of conflicting knowledge and then arriving at a firm position with earned authority. They also sometimes despair that others don’t reason like this, and just believe things (although they can probably rattle off reasons why this is adaptive, since they’ve read a few books about cultural evolution.)

Their taste for secret knowledge also frequently manifests as a quiet acceptance of the taboo. Get to know one closely, and you might find an appetite for some weird shit: the most out-there music and art, or perhaps an intricate kink, or some ceremonial magick practices, or maybe a half-dozen secret opinions that would get them super canceled, no matter what part of the political spectrum they occupy. They want to go right to the edges.

Just one more thought experiment, bro, I promise. Where 5s become frustrating — to themselves and others — is in domains where theoretical knowledge is less helpful, or even a hindrance. The big ones tend to be social skills generally, romantic relationships, and spirituality. Entrepreneurship can be tricky without a cofounder. Managing can be tough, because of, you know, people. 5s can only really grasp these domains when they consent to the humiliation of learning through doing, rather than learning through frameworks. Sometimes, instead, they meticulously craft their lives to avoid the pain of trial and error. This works decently but can limit growth.

And yet they are not really aliens. Whether or not it is consciously apprehended, what they typically want is what we all want: to be deeply seen and loved. To do valuable things, and be understood as valuable. It’s just typically harder for them to get social approval in the usual ways. If you can feel genuine enthusiasm for a 5’s project, and try to understand it with them, it’s very easy to form a rich friendship. Unlike the 4, they often want you to move onto their alien planet, and have a deep generosity re: sharing their passions.

They can have stingy hoarder tendencies. The stereotypical Silicon Valley apartment with a mattress and laundry on the floor, and stacks of books but no furniture? That is a 5 apartment. Depending on your perspective, you can either see 5 tendencies as a laudable detachment from enslavement to creature comforts, or as what the fuck, you’re making half a million a year and you’re wearing those shoes? This stinginess also gets applied to personal energy, which they can hoard. They often don’t ask for normal help from friends, not just because they’re uncomfortable receiving it, but also because they’re anxious about being in a position of future obligation.

Often, they have an all-or-nothing work ethic. What bores them tends to seem painful. But if something captures them intellectually, there’s no stopping them. No type works as hard as a strapped-in 5; the mythical Silicon Valley “10x developer” is a 5 who has found their problem. A story about a 5 friend: he found it difficult to get working at a boring tech job, where the work was mostly beneath him from an intellectual standpoint. But when he found out about a particular Hearthstone tournament format, he realized that with an insane amount of work, he could make a solver that could give him the optimum lineup of decks. He wrote the solver, and won the first such tournament so thoroughly that he broke the format — other top players switched to his algorithm. Sometimes, 5s take advantage of this tendency by making a research project out of a “dumb” hobby. The bulkiest guy I know personally is a 5 who became a weightlifting nerd.

5s typically become scarily effective when they learn three skills: treating reality as a team sport (delegating intelligently and asking for help), learning through execution (fucking around and finding out), and acting under uncertainty (welcoming fear). The cliche examples in this category include Bill Gates and Warren Buffet. These three skills involve repeatedly confronting the nervous system overwhelm — the sense of being invaded by the world — that 5s usually avoid with competence.

The woo angle is that not-knowing, if you make peace with it, opens the possibility of embodied wisdom that can’t be communicated through abstraction.

When unhealthy, 5s take on the self-indulgent time-killing tendencies of a neurotic 7. When healthy, they take on the instinctive, fearless style of a thriving 8.

My instinctive reaction is pure fondness, if we share even a single mutual interest. I love the purity of the 5 taste for knowledge. But the social skills can be tricky.

8: The rock, the bulldozer, the rugged individualist

Strengths: Self-mastery, drive, fearlessness. Human cannonballs who can be powerfully nurturing to those they protect.

Weaknesses: Pushiness, cruelty, defensiveness. A compulsive and annoying tendency to see life as a battle, when often it is not.

On the group hike of life they are out ahead, clearing obstacles and accumulating blisters, and loudly debating which way to go.

Core fear: It’s a harsh world, where the strong do what they can, and the weak do what they must. Surrender control and you will be controlled or annihilated. It’s all up to you, nobody else can be trusted, especially not with your soft underbelly.

You understand the 8 if you ponder the following question. What would you do if you were driven by an aversion to fear, shame, and weakness so strong that, ideally, you would never feel those sensations? Naturally, the answer would be the armor of mastery. You would become confident and commanding, and concentrate your vision on areas of life where there’s winning and losing, and you’ve got a shot at winning. You would want to win the game so thoroughly that further play is at your leisure. Whether it’s at the sorority, the dojo, or the academic conference, the 8 wants to leave their stamp on the matter, to rise above the fray and mark their territory.

The work product of a leader is clarity. And this is why 8s are natural leaders—they distill the world down into actionable problems and clear positions. Think of the reality-warping sloganeering of Donald Trump (the most visible 8). Or the atheistic argumentation of Christopher Hitchens, which was not theologically sophisticated, but instead brutally effective in its simplicity. This is a great gift: 8s are naturals at finding a simple, effective strategy and hammering it. Sometimes this lets you take over the world. But if it’s compulsive, it can be an annoying limitation, which narrows the vision, making the 8 the person with a hammer who thinks everything is a nail. More than any other type, they are likely to give unsolicited advice, or tell you they know what your problem is. An 8 being pushy is perhaps the most irritating personality, period—they will just not let go of that bone.

8s have a sphere of control that varies in size. All 8s tend towards control. But some are primarily interested in self-control, and have a libertarian sensibility. They take care of themselves, and perhaps laugh darkly at the weakness of others, but don’t let themselves become bothered by it. Some other 8s believe that their family, or company, or country, is theirs to command. Depending on the wisdom of their leadership, and their emotional health, this can either be highly welcome stewardship or the worst kind of mafia don behavior, where they relate to the world with an expansive sense of oppositional grievance, and encountering them will go poorly unless you kiss the ring.

Real vulnerability is hard for them, but caring is not. Their care is typically of the “come eat this buffalo I slayed” variety. A dear 8 friend, Aike, is absolutely insistent that I’m ludicrously fed whenever I visit her city, and orders for us whenever we go to a restaurant. And while I’m almost twice her weight, I think her instinct would be to defend me in an ambush. (Queried about this, she responds: “I would absolutely defend you in an ambush and cut off the balls of those who dare to attack with a dull jagged knife.”) How better to demonstrate mastery than to have extra spoils, and surplus strength?

8s like to lock horns. Whether it’s in a fiery debate, physical fighting, or athletic competition, 8s tend to challenge others, and typically respect those who engage more than those who back down, even if the 8’s preference is to eventually win. Returning to Trump: people who don’t understand how he hurled insults at Mamdani and then became his buddy do not understand the 8 personality. For an 8, conflict is a natural mode, which says little about future potential affinity. One of my oldest friends is an 8, and in our first interaction, when we were roommates, he was so disgusted by the intellectual sloppiness of an essay I was reading in the New Yorker that he snatched the magazine out of my hands and threw it in the garbage. I didn’t initially understand that this was a friendly gesture.

There’s a new sheriff in town. While they can be bullies, they can also detest bullies— the incompetent execution of power triggers the desire to usurp. They’re not moralists like 1s, but they believe in a personal code of honor. And typically, they are not afraid of confrontation. This makes them natural activist leaders, and natural ladder climbers, although an open lust for power in less self-aware 8s can sometimes be unstrategic and offputting.

They’re hot and cold, but not in the way this is normally meant. A happy, comfortable 8 is a joy to be around, with an earthy, immediate energy, and often a frank, unselfconscious sexuality. (An 8 tell for me is an energetic sense that the person wants to fuck the universe.) They are present, generous, and playful. But if an 8 is in competition mode, they can become cold-blooded killers, viewing people in their way as mere obstacles. Meanwhile, a disempowered 8, fearful that they will lose control, can go to collapse, anxiety, and childlike grief. This quality of having a few entirely distinct gears is one that loosens in only the healthiest 8s.

But they do like to submit when they trust they’re in good hands. Often, 8s will be devoted to a few chosen teachers or mentors, who they will speak of in glowing terms. (Name-checking the sensei is a classic 8 method of affirming personal authority.) 8s also love assuming the position of mentor, to pass on their way of doing things. What’s more stressful for them is peer relationships where the power dynamic is ambiguous: one-up or one-down is more comfortable than side-to-side. Among these peers, they can exude “wounded hound” energy—this edginess you see in dogs that have been in a lot of fights, a wariness rooted in the assumption that play can suddenly become warfare. Sometimes this becomes a self-fulfilling prophecy.

They have a soft underbelly. Few get to see it. If you’re one of the privileged few, you likely have an ally for life.

The woo angle is that, paradoxically, surrendering to the universal order is freedom, and striving for perfect control is just self-imposed imprisonment.

When unhealthy, they withdraw into paranoid isolation like a neurotic 5, seeing threats everywhere and getting mired in analysis paralysis. When healthy, they access the open-hearted generosity of a 2, using their power to nurture and protect without needing to dominate.

My instinctive reaction depends entirely on the relationship configuration. If I’m not in competition with an 8, I simply love them. They are extremely fun. If it happens to be an 8 who sees me as a rival or obstacle, I just maintain a respectful distance.

2: The giver, the pleaser, the attunement artist

Strengths: Empathy, generosity, geniuses of love. At their best, they can make nearly anyone feel seen and cared for—they have a borderline psychic grasp on the needs and states of others.

Weaknesses: Intrusiveness, manipulation, martyrdom. Neediness masked as altruism. The person who suffocates you with unwanted assistance or deference, then resents you for not being grateful enough.

Core fear: You are lovable only when you’re needed. If you ask for too much, they’ll see you’re worthless and leave. Love is never freely given.

On the group hike of life, they’re making sure everyone has enough water, checking on the slower hikers, and secretly exhausted but insisting they’re fine.

One of my oldest friends, Jackie, is a 2. She’s not necessarily my closest friend. And yet there is something about the bond that’s unique among my relationships. It is the feeling, any time of day or night, that she is there for me. Not via any specific act, but just via her fundamental nature — that is part of who she is. She is someone who’s there, always, for the people she chooses to care about. Recently, I had an exhausting day, and I simply thought about how she is there, and I relaxed. We didn’t even have to talk for her to care for me. This is the astonishing power of the 2 at their best.

Saying that they’re the teacher type is a misunderstanding of their versatility. I have met C-suite execs who are 2s, and managers, and artists, and realtors, and, yes, therapists and teachers. What unites them is being image-focused, but with an image constructed on feelings and outcomes occurring in others. There are many ways to be other-centered, and thus there is a diversity of 2 occupations. They’re easiest to pick out with energy, this ooey-gooey feeling of being met, that, depending on the health and savviness of the 2, will either feel incredibly comfortable, or like too-warm bathwater.

Other types do not totally grasp what it means to be so other-focused. Here is a hint. One 2 told me: “If someone I love says they need something, I feel like I’ve already failed. I should have been able to see it coming.” Really imagine what it would be like to feel this way, and you’ll start to glimpse the 2 existence.

As a result, they can be remarkably attuned to what you’re hungry for—praise, validation, gifts, favors, being seen in a particular way. Especially with avoidant people, who usually resist attention, they possess an instinctive grasp for finding the hard-to-find button. This can make them remarkably charismatic and/or seductive 1:1. The darker side of the 2 is that this can turn into manipulation (now you can’t abandon me), or unwanted help followed by entitlement (you have to pay the price for the gift you didn’t need).

The 2 suffers from a specific form of pride. It is a pride that, in the average 2, must be disowned to maintain their self-image as a giving person. It’s something like: I am the reason that my partner is happy. Or that this pop star I produced is touring internationally. Or that the diners in my restaurant are fed. Sure, other people get the credit, but behind the scenes, everyone knows that it’s me who put the necessary icing on the cake. And given that I’m the one who’s really responsible, they couldn’t possibly abandon me. It seems to me that the emotional health of the 2 is largely based on them confronting this fiction, which is a useful fiction to hold lightly, but a torture device if taken seriously.

And there is a tragedy beneath this pride. The tragedy is that the 2 often holds a covert hope that they will be held and comforted with the same sensitivity they apply to others. But they often end up in relationships with difficult people, out of a natural tendency to rise to the level of their ability. If you want to win the Caring Olympics, pick someone avoidant to be your love treadmill! So the 2 gives all they can, which sometimes is not enough (or not really wanted), and this can infuriate the 2 (thank you to Jackie for pointing this out). Meanwhile, they rarely receive the same level of attunement and charity from others. At its worst, this tendency creates borderline type behavior, when the 2’s resentment is externalized, and others go from saints to monsters in their eyes.

Also tragically, when offered the interest they’re covertly asking for, they are not often comfortable receiving it! While there is a heart-level yearning to be seen, there is a gut-level discomfort with it, because it’s an unfamiliar energy flow, and out of step with their habitual self-demotion. One dead giveaway that I’m talking to a 2 is that they keep redirecting the conversation to my gifts and my strengths, and then hurriedly qualify any compliments or deference I give them. Another is that they talk about developments in their lives largely relative to other people—narrating the states of others as more significant than their own.

As with the 4, “feel your feelings” is often bad stand-alone advice for these people. Not because they don’t repress—often, they repress their anger and resentment. But because they already feel tremendously, as a regulatory strategy, and a spell of anger would typically be too foreign to integrate. Better first-pass advice in a conflict situation, if they can take it, might be: “Think about taking the approach that feels, to you, like being monstrously selfish, cognitive, and tactical.” This will bring them to a point where they are only somewhat more giving and empathetic than the average person, rather than enormously. This will surface a lot of feelings to start examining.

The woo angle is that the most potent type of love cannot possibly be earned, and it has actually always been there.

When unhealthy, their resentment blooms into a full-on collapse into rage and/or depression, as in a neurotic 8. When healthy, they take on the vivid self-awareness and distinctness of the 4, rather than compulsively merging and self-minimizing.

My instinctive reaction to 2s is, ahhh, this is wonderful. And then, sometimes: but I’m supposed to earn the center of attention, why are you just giving it to me?

4, 1, and 7 are referred to as the “frustration” trio, or triad if you’re fancy. These types all have an idealized vision of how things should be, and experience constant frustration at the gap between their ideal and reality. The 4 tries to close it by cultivating specialness, in themselves and their experience. The 1 tries to close this gap through perfection and correction. The 7 tries to close it by reframing everything as positive and seeking constant novelty.

4: The poet, the romantic, the dispossessed one.

Strengths: Depth, creativity, originality. The true aesthetic orientation: a divine discontentment that creates much of humanity’s great art and culture.

Weaknesses: Victimhood, moodiness, indulgence. Bitterness. “I’m such a disaster,” says the 4, either smugly or despairingly, after another predictable act of self-sabotage.

Core fear: You are fundamentally flawed and irredeemable, and all the preening you do only serves to accentuate this. You’re as disgustingly normal as everyone else, and yet you still can’t figure out how a person should be.

On the group hike of life, they just happen to be taking their own route, which seems roundabout but satisfies their private goals.

Difference is a funny thing to base your identity on. Because you need someone to notice the difference, an audience to find you semi-relatable. Too close and you merge, losing your distinct markings. Too far and you’re just a complete unknown. This is the strange dance of the 4. They want to be seen and admired, but not reduced or figured out. If you can grasp this wonderfully perverse instinct, so much about the 4, a type that is otherwise confounding, becomes logical. All the peacock-ish adornment, in costume and mannerism, combined with the tendency towards isolation and guardedness — it’s the straightforward product of a conflicted strategy.

The instinct towards specialness creates a natural contrarianism. If you tell them to go left, they will develop a fondness for right, or at least apply a little rightward nudge to the trajectory. Falling into your agenda completely can represent an existential collapse. This applies more generally to gender, political, and professional scripts. They will find a tweak on your way, even if they don’t realize they are mutating the instructions they are given. And when things get too stable, too figured-out, average 4s often blow shit up. They’ll sabotage relationships, find ways to get fired, uproot themselves continuously. This is a defense against ordinariness. Better to destroy the mundanely pleasant circumstance before you catch yourself enjoying it.

Many 4s are drawn to outcasts — schizophrenics, disgraced starlets, nerds, bad boys, cult leaders, monsters in cinema. These figures represent true authenticity, a disconnection from the impositions of societal order. They are unplugged in a way the 4 can’t quite be, completely. Equally, the 4 is drawn to what is aristocratic, rare, refined, and timeless. “Broke with expensive taste” is thus a common 4 pose, whatever the underlying net worth is.

They are easy to spot. Fully 1/3 of people introduced to the Enneagram misdiagnose themselves as 4s, but this is instantly dispelled once you know a few. Of the types, they have the most characteristic energy. It is like standing on the beach at twilight — an abyss is calling. To get a sense, listen to Fiona Apple trying to explain herself. (Although note that 4s can act, as can any other type, so you might not glimpse this energy upon first meeting.) They often have a fondness for aliases, and/or are fussy about the pronunciation of their name. They are often defensively sarcastic. Their melancholy is rich and lovely, unless they have chosen to blame it on you. Among my age cohort, 4s are often interested in androgyny, but I suspect younger 4s might be leaning back into traditional gender expression to squirm away from the expectations of liberal parents.

Follow them into the darkness. More than any type, the 4 is unafraid of negative emotion. This makes them wonderful companions in the dungeons of human experience — they can make you feel accepted when all is lost. You’re completely soothed, not because they are trying to fix your despair, but because they don’t see it as an issue. I receive coaching from a wise 4, and he never fails to catch me out in my falsity, partially because of what seems like an intrinsic desire to glimpse the depth I’m so eager to obscure.

They live with a sense of absence, a nostalgia for something beautiful that hasn’t happened yet. This is created by their constant urge to search for what is whole, rich, real — the catch being that this is the only 100% reliable strategy for missing out on real transcendence. On an interpersonal level, this feeling of absence manifests as painful self-awareness. They look out at people getting by normally and wonder: am I too special for this world, or just more fucked up than average? My coach, Gareth Holman, comments: “If you’re an outsider, you freak people out, but you can also illuminate them. If you’re insecure, it’s hard to be that person.”

Their success depends on what they do with this essential yearning. Think about Bob Dylan. There is a constant sense of searching for the answer in his music. Did he ever find any answers? Not as far as I’m aware; and yet, he took the yearning as a continuous prompt for further search, and forever changed our culture in the process. 4s can become outrageously productive and original if they fall continuously into the yearning, really embrace it as a fuel source, rather than taking it seriously as a sign of inadequacy. Adrienne Lenker and Karl Ove Knausgård are two current examples of 4s who have settled into this mode, to profound results.

It’s common to note that 4s can be dramatic, finding occasion for large emotions in light of relatively minor developments. (Returning to Dylan, he wrote “When the Ship Comes In,” a song of divine retribution, upon being given guff by a hotel clerk.) Are these jags of emotion “false?” That doesn’t quite get it right. It’s more like the 4 can create aliveness, contact reality more thoroughly, through being a feverish tourist of their experience. This Wallace Stevens line captures the dynamic: “They said, ‘You have a blue guitar, you do not play things as they are.’ The man replied, ‘Things as they are, are changed upon the blue guitar.’”

The woo angle is that the 4 can realize that the ache of separation is, itself, a part of the wholeness of presence. The yearning is literally made of the substance it desires.

When unhealthy, 4s start looking for a lover or savior to thrust their ungainly cravings at, like neurotic 2s. When healthy, they take on the responsibility and standards of a healthy 1.

My instinctive reaction to 4s is to be fascinated, often at a slight distance.

1: The perfectionist, the critic, the saint in training.

Strengths: Integrity, honesty, energy. High standards and the resolve to follow them. A bullshit allergy, in themselves and others, that sometimes makes genuine heroism the only option.

Weaknesses: Suppression, moralism, disowned pride, stress. Score-keeping and pettiness. Explosiveness and dysfunction resulting from failed efforts at self-containment.

Core fear: You will never find a way out of your corruption and mess. All of your purported goodness is a thin veil over the roiling mass inside, and this is true of the world, also. Better hang onto that separateness, who knows what would happen if you lost that thing!

On the group hike of life, they have figured out the objectively correct route, a virtuous path that few follow with them.

They are characterized as the religious or moralist type, but this is best thought of as a consequence of their core mechanism, not the root of it. At their heart, 1s are conflicted, torn between their intense emotions and their rational superego. They are their own rigid parents, whipping themselves into shape with guilt and shame. This creates a natural yearning for clear codes of behavior, and a sense of pride when their corrective internal agenda is successfully maintained. Meanwhile, they are threatened by the chaos of others, who ought to do the right thing, as they do.

This inner battle also creates a deep sense of shame and grief — the shame and grief of self-submission. The beaten-down part of the 1, the tempestuous locked-away child, is still in there. Thus, a predictable vicious cycle: when this shame is encountered, its chaotic power triggers more suppression. A 1 can easily spend their adult life this way, because the coping mechanism so often creates high performance in work, and an orderly, if not fully satisfying, way of relating to others. Meanwhile, this can create resentment: while they keep everything bolted down, everyone else is just coasting along in their sloppiness and self-indulgence.

They turn anger, fear, and shame into competence and diligence. If you look carefully, you can see this process happening in real time. Something imperfect comes into the 1’s world, either the misdeed of someone else, or an undesirable emotion, or a mess in progress. They purse their lips, clench their jaw, or take a sharp inbreath. Then, they respond, turning the rigidity into a coolly chosen next move, with just a hint of barely noticeable fury. I think of this as “calm lightning,” and I find it to be captivating and a little scary. (Reader, I married one.) Unfortunately, the inner accompaniment to this process is often a scathing critical voice.

If you are not moved by the genuine integrity of the 1, then you are not paying attention. In this haphazard world, so many of us are looking for an excuse for our sloppiness, but 1s are constantly attempting to rise above it. When this works, they can be machines of loving grace — the whole drama of the 1 is visible in this video of Thomas Keller. Ironically, to maintain this rarefied level of performance, 1s have to be forgiving and kind towards their normal human needs, and normal human sloppiness. Otherwise, burnout, addiction, or another form of involuntary self-restraint will follow.

There is a notable division within the type, between extroverted-leaning and introverted-leaning 1s. The former are your pastors, teachers, and campaigners—moving the world towards goodness and order through relationships. The latter are your craftspeople, chefs, philosophers, and architects—righting the universe through more private labor. Both kinds can be natural founders, in the profit or non-profit worlds: entrepreneurship is a potent method of sending a message. Though the two subtypes are superficially different, they are united by the obsession with the straight and narrow path: punctuality, honesty, consistency.

The bitter irony of 1s is that they are the type most desperate to seek divine grace, but most capable of blocking it by remaining in a stance of perpetual judgement. I’ve met a number of 1 meditators who systematically miss what is really meant by the Zen maxim: “Without thinking of good or evil, in this very moment, what is your original face?” My wife comments: “There’s something I’ve come to see as central to the 1 character, which is a default stance of ‘no’ towards the world — things aren’t good, you can’t let them in to pollute you. This makes it really hard to accept grace and come to see holiness in the everyday.”

Looseness and ambiguity bothers them. “What are we doing here” is a key question 1s are asking, with the answer hopefully coming in the shape of a standard that they can meet, exceed, then enforce. This makes 1s terrific organizers and managers. However, there are two key failure modes. The first is arbitrarily arriving at high standards others don’t agree with, and then becoming furious at others’ lack of compliance. The second is trying to create false order in domains that are resistant to order — or a simple refusal to believe that such domains exist. This is an intellectual deficit they share with the 5, a blinding desire for reality to be neater than it is.

Their emotional distance isn’t personal. It’s just that they let you into their emotions only to the degree that they’re letting themselves feel them. This is often not apparent to them, because an apparent defense mechanism is a shitty defense mechanism. And when the 1 opens up, you see a beautifully childlike quality, like a kid getting out of detention. (It also just is a kid getting out of detention.)

The woo angle is that from the perspective of their shadow, their ego is the thing blocking the light — the inner ugliness is redeemed and transformed only when you actually own it.

When unhealthy, their inner drama takes on the quagmire quality of the neurotic 4. When healthy, they take on the lightness and fluidity of a high-functioning 7.

My instinctive reaction towards them is admiration, and a bit of confusion. They are as different from my type as can be, and I so appreciate their striving. But I’m also like… why?

7: The optimist, the dilettante, the socialite.

Strengths: Positivity, curiosity, versatility. Speed and buoyancy. The person who can genuinely fall in love with everything, and wants you along for the ride.

Weaknesses: Gluttony, flakiness, cowardice. Glibness, vacuity. The person who can convince themselves they’re in love with everything in order to avoid deprivation or pain.

Core fear: You are cold, bored, and alone, pigeonholed in a dreary pen, while everyone else is having fun without you. You stopped moving long enough that someone can finally see you, and, oh look, you have such obvious limitations.

On the group hike of life, they can’t decide whether the smell of eucalyptus is the most beautiful thing ever, or the wildflowers, or your boots, and they would like to discuss all the options.

Much of the character of the 7, my type, becomes clear if you extrapolate the consequences of one odd property. We are stimulated and pleased by change, whatever it is. This is unusual — if you list the factory setting human fears, change is supposed to be one of them. But when change is merely amusing, everyone you haven’t met could be a best friend, every skill you haven’t learned could be your new personality, every city could be your new home. This is a superpower which is also a hideous temptation. Almost before you begin to feel pain or boredom, you can already think of a dozen opportunities for stimulation. When I’m trying to type someone, I sometimes ask them: “if I kidnapped you, took your possessions, dropped you off in Russia, and told you that you had to find your way to Myanmar, would you find this fun?” An instant and genuine “yeah” is a 7 giveaway.

The tempo is fast. It is a hungry, impatient speed. I am thinking to get to the end of the thought, reading to get to the end of the book. After a beautiful experience, I think, “thank God that’s over,” and dash to the next thing. As a result, we are natural generalists. I’ve forgotten about more interests than many people ever have. Recently, my wife was talking to a friend about structural issues with science funding, and he said, “Sasha has a great whitepaper about this.” I thought he was joking, and then I realized that I actually had coauthored such a document, during the five weeks when I was thinking about a career in public policy. If he hadn’t mentioned it, I may never have thought about it again.

We like to play a little dumb. In truth, 7s can be formidable — our resilience and curiosity makes us fast learners, and our restlessness often takes the form of abundant creativity. Our allergy to structure and routine is counterbalanced by our effortless, endless motivation to pursue our genuine interests. But we like to pretend we’re less capable than we are, because owning up to our true capabilities would mean adopting a mantle of responsibility. Of the 7s I’ve met, a suspicious number are talented people unconsciously (or consciously) choosing mediocrity as a defense, and it is a mode I can also lapse into if I am trying to outrun my anxiety.

To soothe myself during insomnia, I used to look up cities in China on Wikipedia. There are so many cities in China with over a million residents. You can get interested in each one. You can look them up on Google Street View or YouTube to sample the pedestrian experience, maybe while listening to a Melvyn Bragg panel discussion on Zoroastrianism. Or you can just think about how “Ulaanbaatar” has far too many “a”s in it. In this mental spinning, what is real fascination, and what is just decorative distraction? It took a thousand or so hours of meditation for me to start teasing this apart. And even then, it is not always obvious.

We can be quite caring, because we want you to join in on the good time. I am uplifting without even trying to be. Your mood cannot drag me down. When my wife had a brief cancer scare, and she texted me about it, my mind was instantly filled with a rapid-fire montage of how I would lift her sorrows. I thought of a great “you have cancer” party we could host. I considered the wig possibilities. But we can also be extremely insensitive, because we expect the world’s moods to be alterable and flickering as ours, and we don’t take the time to consider our remarks. Occasionally I say something hurtful, and then am surprised that I am being listened to.

Negative emotions are magnified enormously — one dreary afternoon, and we are convinced that our whole life is a tundra of despair. Everything good in life can be ruined unless we learn to stop taking this perception seriously.

Our appetite for dodging this despair gives us a reputation of being hard therapy cases. Our central defense mechanism is fun, and the world rewards it. Okay, it does not age gracefully: the 48-year-old restaurant manager still doing cocaine on a Thursday is a 7. But the 7 is quite capable of spending their whole life in flight from themselves, while simply experiencing this as the world being interesting. I went through a few genuinely traumatic circumstances without ever really noticing my pain. Instead of grieving, I got on planes, stuffed my face, wrote a book, had three crushes per month. And then when I stopped and felt my heart for the first time, I was shocked — I had been laughing and laughing, walking around with a knife wound.

To have a rich life, 7s need to thwart their central instinct and commit. To a vocation, sure, and a relationship, yeah, but most importantly, an honest reckoning with our real limits. As I type that, a chill runs through me: limitation as a concept makes me uneasy. And yet, every iota of true value in my life has come from it. Meanwhile, in periods of my life when I allowed myself to be a free agent, nothing real happened. It turns out that compulsive optionality maintenance is not true freedom. But you cannot force 7s to get that message — I received it suddenly one day by the grace of God. Sometimes, I meet 7s who are still frantically trying to feed their hungry ghost, and I think, “oh, I hope the comedown from that realization is gentle.” Anthony Bourdain’s life and death are both instructive for the 7 who wants to understand how they can thrive and, equally, explode.

The way I’ve tricked myself into appreciating depth is by adopting the position that complexity is where infinite adventure actually lies. Fortunately, this appears to be true.

The woo angle is that if you really relax all the way, like all the way, you discover the ultimate prank, which is that consciousness is made of bliss, and that candy-floss giddiness you were manufacturing was never necessary.

When unhealthy, we take on the self-suppression of a neurotic 1, in an attempt to rein in the gluttony. When healthy, we take on some of the depth and seriousness of an actualized 5, and maybe just a touch of asceticism, for a treat.

My instinctive reaction to 7s is pretty gendered. When I meet 7 women, it is often like meeting a sibling: there is an instant click which is completely platonic. (Thank you to two such women, Carly Valancy and Jenny Huang, for their help with this piece.) When I meet 7 men, unless they are uncommonly healthy, I see my own psychology and instantly break out in hives.

These are not meant to be definitive takes on the types, but instead personal renditions, focusing on the aspects of each type that serve as hallmarks for me. Undoubtedly the takes are influenced by the examples of the type I run into, as a weird member of a WEIRD society. My understanding of each type continuously shifts and deepens, so all of this is pending change. And I am a 7 with a side helping of 3, for what it’s worth.

3, 6, and 9 are the so-called “attachment” trio. This means that their default stress response — which is to say, their personality structure — is built on “attaching” to a reassuring state of affairs, an equilibrium or image that is comfortable, often built on the expectations of the environment. The 9 does this by merging and harmonizing. The 6 does this with situational awareness and stress. The 3 does this by chasing excellence.

6 and 9 are the most common two types in the whole system. If you are looking to get better at Enneagram typing people, start by disconfirming the hypotheses that a given person might be a 6 or a 9. This makes sense: given that they are the most groupish personality profiles, if I were God, I would want a lot of them.

All three are diverse in their presentation, given that they survive by adopting value systems found in their environment, and there are plenty of those. To spot them, you have to look for certain navigational styles, rather than surface features.

6: The pragmatist, the troubleshooter, the fixer.

Strengths: Responsibility, awareness, self-sacrifice. Diligence. At their best, sensitivity meets energy, toughness, and commitment. They are practical, quick team players who love to tackle the problem and build lasting bonds. Their intensity is electric, and they are often funny, because worry is a great source of humor.

Weaknesses: Rigidity, paranoia, worrying. Fussiness, resentment. The busybody colleague who treats minor issues like Defcon 1. The QAnon subscriber who keeps boycotting random toiletries because of the chemical they’re worried about that month.

Core fear: You can’t trust yourself and nobody is there to tell you what to do. You stuck your neck out too far and look what it got you. Being tricked, trapped, blamed for an avoidable failure. You’re off the map, because you followed false directions, and where you are is just existentially wrong, and you will never find your way back.

On the group hike of life they are the ones constantly glancing between signs: orienting features on the landscape and their fellow hikers, who they might imitate or support.

“Everything is wrong.” This is a story that I’m used to hearing from 6s who have their lives pretty together: like, years of financial runway, at least one supportive relationship. But they instinctively keep an eye on the possibility of ruin, while also noting how far they’ve fallen short of their potential. This mental swiveling, from the possibility of peril to the indignity of compromise, is a perverse self-soothing mechanism. It stops them from resting in ambiguity, which is a more fearful place. This is unfortunate, given that ambiguity is the beginning of potential.

They often have a plucky, wiry, likable energy. In order to not be left behind, they often master that basic human skill, recruitment. Being befriended by a 6 is not the ooey-gooey experience of merging warmth, which you often get with 2s. Instead, you are being turned into one of the gang, a buddy, a chum. Get used to being asked for your opinion if you know a 6 (and then sometimes having your opinion disregarded when another source contradicts it). When 6s are healthy, this wiry wariness is met by an embodied solidity, and the result is formidable and beautiful.

Often they are pent up. This is because of their basic pattern: they accommodate and compromise, in order to avoid going astray. Then, they find themselves lingering too long in frustrating jobs, friendships, and relationships, which all are selected/engineered to cater to a watered-down version of them. It is easy for them to think that the world could not possibly take a less restrained version of their ambitions, or their emotions, or their sexuality. It is harder to believe that the self-restraint is a cruel self-imposition, which may have been adaptive early in life to suit rigid caregivers or young peers, but which ultimately underestimates the flexibility of the world around them. Sometimes they escape from one prison to find that the confinement was their doing, and it is portable.

Surprisingly, they are sometimes fond of a bender. If you dig into a 6’s life, you will often find jags of irresponsibility, which seem like breaks in character. But it’s not really: nobody can manage themselves that constantly, and 6s sometimes relieve the tension of grimly keeping up in one area (career, for example) by letting another area fall apart.

Sometimes they think they are 4s. This is a grievous mistyping, but it makes some sense. They typically have a suppressed individual streak — the result of living with all of that self-managing. Thus, they are painfully aware of their difference, like 4s. But what they cannot imagine is yielding to their difference, whatever the consequences, which is more typical of the 4 lifestyle. “I’ve always wanted to be an artist, but I’m keeping an eye on where the job market is going” is something I’ve heard from multiple 6s, and zero 4s. And though 4s also complain a lot, the 4 complains to reinforce their specialness, whereas the 6 complains to test your sympathy.

They are skeptics until they aren’t. I have a suspicion that someone is a 6 when I introduce them to the Enneagram and they say, “well, I could be that one, or that one… I have a little bit of this one, too. I guess this system just doesn’t apply to me. Don’t all of these apply to everyone? Maybe this is fake. Or maybe I’m a 4? Or an 8?” This sorting/surveying/questioning action is the mental character of the 6, which is all about fussing, comparison, and disconfirmation. However, when 6s are bought in after this ruminative process, they buy in hard — often they have deep loyalty towards friends, family, mentors, treasured cultural artifacts, etc.

Many 6s seek therapy, coaching, and mentorship. Part of the impulse is simple self-improvement, but part is an urge to relinquish authority. It is dangerous for 6s to get too attached to the words of a spiritual teacher or mentor, whose models 6s might adopt wholesale as a new identity to defend, or a dogma to squeeze into. This is better than having a harsh, unsuitable authority figure as an inner supervisor, but it falls well short of the real prize.

They have teeth. Sure, they attempt to blend in. But they are resourceful — they will fight for what they believe in, whether that looks like being part of an angry mob, or standing up to a bully. Some, the so-called “counter-phobic” 6s, have a habit of figuring out where boundaries are, and what is reliable, by pushing: Malcolm X, John Lennon. This defiant variant can look superficially vastly different from the classic presentation — but if you just look at the mental character, you will see the same wiry, wary energy.

A 6 friend tells me: “The most annoying part of 6ing is that Bad Things Often Happen and your vigilance really does liquidate into golden coins at times, they’ll even compensate you for it at a career level. But when you are a Neo, every bullet looks like something to contort yourself across the field of reality to dodge. Some were never going to hit you in the first place.” -Allie Pape

The woo angle is that when 6s locate their inner authority, their vigilance stops being a cage, and starts being a helpful companion that keeps them from falling off the rails. The quickness that powered their spinning is liberated into spontaneity, and they can shape the world, rather than just responding.

When unhealthy, their worry takes on an image-conscious flavor, like a self-important 3: look how far I’ve fallen! What must everyone think of me! (Typically, everyone is not thinking of you.) When healthy, their ability to hold ambiguity without needing to “snap to grid” takes on the flavor of a healthy 9.

My instinctive reaction to 6s is that I want to take them out dancing; I see how crunched up they are and want to participate in their uncrunching.

Note: I find 6 to be perhaps the hardest Enneagram type to grasp, and the worst described by Enneagram books. This interview from Courtney Smith is a wonderful resource.

3: The optimizer, the example, the shiny person.

Strengths: Drive, charisma, conscientiousness, a neon-like glow. At their best, they are annoyingly great, matching relentless individual achievement with magnanimity and practicality. Good-hearted elites who do right by their gifts.

Weaknesses: Falsity, narcissism, a tendency towards burnout. That person who thinks they’re hiding how tactical they are but absolutely isn’t. They lust for the finest things in life but can’t even really enjoy their prizes.

Core fear: Everyone knows how worthless you are deep down — they didn’t fall in love with your fake self, or even notice it, and now you’ve got no real self to fall back on. Or, if they did fall in love with your fake self, even worse — they will never love you for who you really are. You want to be seen, but dear God, not like that.

On the group hike of life they are at the front, looking out over a vista, in a pose that just happens to make them look like statuary.

3s can present as everyone’s best friend. They are often charmers. When talking to them, one can feel smoothly handled, which, depending on your mood, can be wonderful or irritating. They are deft at navigating around awkwardness before it even appears, calling you by your first name but not in a weird way, offering a canny compliment, keeping the tension at a minimum. But it can be hard to get real vulnerability from them, unless they will directly benefit from it. This is why Bill Clinton is my archetypal 3. “Blank gleam” is a 3 tell for me, an impersonal suavity.

Under the surface, they often contain huge, childlike emotions. Most 3s are not even aware of how much they are optimizing in order to please others. If you have to track a value system, that is far too slow. You have to become it in order to possess real facility. What is concealed is the “don’t abandon me” desperation underneath, and it is often immense. As a result, it is magnificent to see a 3 finally open their heart. And though 3s are often reluctant therapy patients, when they finally turn their competence towards acquiring real emotional intelligence, they flourish.

They possess initiative, and, equally, impatience. They want to be where it’s going and make it happen now. This desire typically blooms into genuine competence in multiple areas — many serial entrepreneurs are 3s. However, this speed emphasis can cause them to cut corners in pursuit of the goal, to overpromise, to be carnie barkers for the gleaming future self they are working on. This also makes them good at spotting talent: since they are so used to seeing themselves as an exploitable resource, they can spot resources in other people, whether to identify future rivals or colleagues.

They are often desirable. If not naturally beautiful, they will work to burnish their other assets, until they are magnetic. As with all the positive traits of the 3, this is a double-edged sword, the pedestal that can become a prison. I remember one striking, slender 3 telling me: “if I start loving myself, I’ll get fat.” This mindset is effective in attracting admiration, but also in making the admiration seem counterfeit. If you attract affirmation by polishing and presenting select facets of yourself, it can become troubling that the other facets aren’t receiving love too.

Often, the confidence of a 3 is surprisingly contextual. Catch them in their environment, where they know how to be, and they absolutely ooze self-assurance. But they can have more trouble in situations where they are visibly the odd one out. Learning something they aren’t naturally talented at is painful, as is entering periods of uncertainty between achievements. Thus, the maturity for 3s is not necessarily in giving up on the project of excellence, but rather learning to punctuate it with relaxation, and to allow for “explore” as well as “exploit”.

The 3 can find it especially redemptive to realize that ultimately, they are not a problem to be solved — not every one of their issues is a resolvable pathology, or a peak to be surmounted. They are also loathe to accept this, because they are so good at making shit go that it’s initially dispiriting to give up on taming the wilds of their subconscious. Being in a place of perpetual stress is typically safer for them than a stance of acceptance.

Recently, a 3 said to me, “it’s amazing how the solution to almost every problem is feeling your feelings.” My response was: that is not generally true, but it’s probably true enough for you! 3s are so practiced at throwing competence around that, if they are in doubt about how to continue, it’s likely because there is some humiliating emotion they have yet to face.

They often possess social awareness. Understanding who is really powerful in the room, who is trusted and who isn’t, what the motives of all the players are — this view of the game board tends to make 3s savvy operators. At the same time, this tactical lens works less well in the domain of casual friendship, and also overestimates how tactical the world is, at large. Thus, a trap that 3s can fall into is performing for people who have no need of the show. Many people, as a result, admire 3s more than like them.

The woo angle is to realize that they still exist when they are not performing — they will not be destroyed by the shattering power of true intimacy, or the pain of anonymity. Ironically, real belonging happens when you stop trying so hard.

When unhealthy, their fear of falling short causes them to numb out and collapse into themselves, like a neurotic 9. When healthy, they acquire the giving pragmatism of a 6.

My instinctive reaction to 3s is that I want them to be real with me, and I try to give them the chance. Sometimes they partake in it, and sometimes they are repulsed.

9: The harmonizer, the cooldown artist, the spacious one.

Strengths: Relaxation, perspective, openness. Stability. When healthy, they can take in the whole panorama of experience, balancing all the perspectives and options before them, and yet still make a firm decision. The sage who does nothing, and yet everything is accomplished. And they can instantly civilize even the most difficult personalities.

Weaknesses: Aloofness, vacillation, dissociation. Manipulative diplomacy. Stubbornness that manifests as a simple refusal to face the obvious matter at hand. Never dares to get hotter or colder than room temperature.

Core fear: Disharmony, being cut off from the flow they carefully maintain. They uncorked their shadow desires—their anger, their preferences, their separate self—and the unity shattered. Now they’re stranded, stuck, drying out on a thin strip of land because they came ashore from the local maximum.

On the group hike of life they are maintaining a steady pace with easy steps, seemingly a part of both the sweep of the valley and the other hikers.

Everyone thinks that Ringo was a useless Beatle. But if you watch Get Back with any attention to the social dynamics, it becomes clear that the band would’ve exploded without him. His quiet generosity of spirit adds a gentle buffer to the other three, who are all challenging people in their own way. This is the genius of the 9 — to make others more tolerable, to provide a broad sky in which thunderclouds and rainbows are equally welcome.

“Should is the most violent word in the English language.” This is an attractive idea that can be deeply dangerous for some personality types. One of them is the 9, a personality type that already excels at passive refusal. Given their talent for endless self-soothing, constraints (deadlines, obligations) can provide helpful prompts to action. But they have to be authentic constraints, onboarded with real buy-in. Otherwise, 9s can be incredibly, silently headstrong, shrugging out of any lasso. Bartleby the Scrivener can be read as a dysfunctional 9.

They are often called stubborn, but I think this fails to capture what it feels like to be on the other end of it. With a 9, you encounter a heavy solid that becomes a slippery liquid. They exude a wonderful feeling of being really there. But then sometimes when you reach to grab them, they slide out of view. So it doesn’t feel like you’re hitting a wall, so much as there’s nothing there pushing back.

To think they are necessarily slothful is to misunderstand. There are plenty of high-achieving 9s, Barack Obama being the most recently notable. What they are is tuned into a wavelength. What they notice is departures from that wavelength. So, they could be comfortable blissing out at a rave to deafening drum and bass, or marching with their regiment, or curling up by the fire. What they are not as happy with is sudden spikes, rearrangements of relationship, a script getting flipped.

“This is fine,” said the cartoon dog, while the house burned down. The 9’s talent for merging with the circumstance can also become self-abandonment. Like the 6, they can coast into being totally out of sync with their genuine wants. But unlike the 6, they aren’t necessarily aware that this is happening, or consciously resentful about it — they are just “going with the flow,” tricking themselves into being alright with subpar circumstances. This can have the unexpected, undesirable side effect of turning people around them into tyrants; 9s often don’t give people helpful appetite-restricting pushback. At the darkest ends of human experience, this can make them fantastic enablers.

They often make absolutely wonderful partners. Their seemingly infinite reserve of patience is a natural wonder. Less patient types, like me, simply cannot understand their deep capacity for what the kids call holding space. Give them your neuroticism, your aggression, your fear. They will take it all, meeting you with stabilizing acceptance — until they get passive-aggressive, or just nonexistent, shrinking away from you as if you’re a piece of disorienting static. This is what can make them deeply frustrating partners: when the going gets tough, they habitually become unreal in order to survive.

Fall in love with your anger seems like nearly a complete path to enlightenment for a 9. But not because that one step is simple: their anger is so swaddled in layers and layers of coping that many latches must be undone before they can embrace conflict without resistance. At average levels of 9 development, the anger is experienced as a constant low-level irritation, an ocean of endless nitpicks — and by the time they rise to open conflict, it’s way too late. Meanwhile, I knew I could trust a 9 friend when she casually yelled “fuck you” at a motorist cutting us off.

They are instinctively drawn to meditation, spirituality, and prayer. They intuitively get the non-me-centric view of the world that is the core of most wisdom traditions. But they can also be skillful abusers of spiritual tools, using them to zone out endlessly: gentle dissociation is the prison toilet wine version of samadhi. Watching sports will also do, or scrolling, any amniotic fluid to get submerged in.

The woo angle is to realize that showing up fully—with their true preferences and conflictual emotions—doesn’t shatter connection but deepens it. True union requires differentiation.

When unhealthy, their vacillation and worrying takes on the endlessly waffling character of a neurotic 6. When healthy, they take on the forward motion of a 3.

My instinctive reaction to 9s is that I like them so much. And I try to be at peace with the feeling that I may never really know whether they share my affection.

However, I also learned that people who are into woo and woo-adjacent healing practices are terrible at precision. Thus, the level of scientific rigor in popular trauma books is zero, and when healer types use the word “trauma,” they can be referring to one or more of about 6 different phenomena.

One of these phenomena is something I call “Gnar.” I find it fascinating because it has nothing to do with what most people think of when they think about therapy.

What is gnar? It appears to be the residue created by repeated repression. It is the metaphorical gunk in someone’s system caused by bottling stuff up.

But what is this residue composed of — literally what is it? Patterns of muscle tension? Something something nervous system? Obviously I don’t have any satisfying answers, and, after browsing some books on the subject, I’m not convinced that anyone else does.

Fortunately, releasing gnar works, whether or not we have good science about it. I’ve seen gnar release up close, and personally experienced it, and it is undeniable and unforgettable.

And from a practical perspective, it’s not that complicated. Let’s say the human system is like a pipe organ, and each pipe represents an expressive potential — an emotion or a mode of engagement, like receiving attention from a group. These pipes can become blocked by habitual suppression, and sometimes the block is made of gnar.

People who routinely suppress their emotions and desires, or resist intimacy, sometimes create a backlog of gnar1. They become increasingly tense, in ways that are visually apparent from how they talk, move, breathe, exist. They also get increasingly defended, as greater amounts of suppression require more avoidance of potentially triggering experiences.

Then, if they’re lucky, they let it out, and they are suddenly less cramped up. Changes can be dramatic and immediate. This what’s happening when people report life-changing effects from doing weird shaking exercises. It is different from garden-variety, lowercase-t trauma in that it is not typically tied to a specific memory — although release is sometimes accompanied by a swell of related memories.

Some dramatic examples:

• A few years ago, I met a woman who complained to me that she’d tried all sorts of meditation and therapy techniques, and nothing worked. On the personality level, she was kind, but flat and withdrawn. Later that year, she did a psychedelic healing session, in which she screamed in anger for several minutes. A few months later, I had a call with her, and I might as well have been talking to a different person. Her emotional range and presence had been grayscale before, and then it was Technicolor.

• A long-time meditator I know told me that his seated practice had become increasingly stale. He started doing standing practice, and found that if he didn’t control his body, it “wanted” to make all kinds of awkward jerking motions, often accompanied by grunt-y vocalizations. After several days of this, his level of bodily awareness and pleasure increased, and he found experience permanently more vivid, as if a veil had been lifted.

• An acquaintance who had tried many meditation and healing modalities to take care of lifelong self-hatred and hyper-vigilance found Shamanic Dearmoring, an intense bodily release protocol that’s too weird to describe here, and after month of resulting emotional volatility, is much better, like “now I feel life has meaning” better.

• Someone I met attended the Hoffman Process, a therapeutic container designed to undo parental conditioning. Nothing was really working until an anger release session, where he hit a pillow with a baseball bat repeatedly and sob-screamed. By his telling, he had been your typical picture of a tense, emotionally distant high-achiever, but changed instantly, becoming more available to himself and others.

• In a yoga workshop after my divorce, teacher told me, specifically, to stay in a deep hip stretch longer than I wanted to. “Feel the anger as it comes up,” she said. “Fuck you fuck you fuck you,” I thought, as anger came up. Then, I lay on the floor, and involuntarily began trembling and sobbing, as waves of sorrow passed over me. Note that I really did not want to do this: I was newly single in a room of cartoonishly hot yoga women. But the emotion had taken over. As I wept, I experienced a rapid flash through memories of all the love I’d tried to give to people who didn’t want it. In the days after, I noticed that a romantic pattern of mine — being attracted to unavailable women, and turning away from healthier opportunities to commit — had vanished.

• Last year, I was at a gathering with a man on acid. He started lightly trembling, and asked me for advice. I suggested that he might see what it would be like to encourage the shaking — what if it wanted to be a noise, or a full-body movement? He began shaking violently, groaning, and occasionally retching, and I sat with him through it. At the end of the trip, he said he felt much lighter, and he reported subsequently that his emotional clarity had vastly increased. This matches my subsequent observations of this person, who I’ve seen a few times since then.

• More generally, at many silent meditation retreats, the first few days are uneventful, but then practitioners start experiencing spontaneous episodes of shaking and sobbing, and sometimes volcanic rage. Often, deep states of meditative absorption follow these releases. This reliably happens to me in solo retreats I undertake.

From one angle, these anecdotes are all the same: they represent the emotional equivalent of taking a long-overdue shit. It is just “I cried and then felt better” x 100. But there is also dissimilarity. How important are the differences? Are there meaningfully different families of emotional release experience, each with different optimal conditions and side effects? This is yet another unknown. The answers may lurk in the tacit knowledge of the best therapists.

Speaking of therapists — as you might expect, there are different schools of body therapy with different explanations for the gnar release process, different opinions on how central it is, and different procedures for facilitating it. Some encourage violent cathartic episodes with little post-release contemplation, while others encourage a steady drip-drip of smaller releases, with more focus on narrative. I don’t know which is better, and I suspect that practitioner skill is really what matters here, as with therapy generally.

You may notice that two of the above anecdotes feature psychedelic drugs. Based on what I’ve seen, they are not at all necessary for releasing gnar, but they can be handy for interrupting default patterns of suppression.

Gnar seems difficult to study. For one thing, it is difficult to predict in advance which gnar release protocol will work for a given person. You just have to try stuff — so, running a trial on one technique is unlikely to yield interesting results. Arguably, it is less about “technique” than it is about engineering a situation where bodily reactions aren’t interrupted by top-down control. One common attribute of big gnar release experiences is feeling like the emotion is piloting, not the ego.

Perhaps this is the primary blocker for most people in releasing gnar: we associate control with emotional health, and fear losing ourselves. Generally, a fine principle, but tragic in cases where temporarily losing ourselves is what would really help.

Gnar release appears to be a finite process. In my own case, after two large experiences, and maybe twenty smaller releases, I feel quite thoroughly de-gunked.

Those who need to release a big glob of gnar can do conventional therapy for decades and see no results. Then, they might go to a gifted somatic therapist, and have a staggering emotional release, and their world is new again. Such events cause some to believe that all suffering originates in somatic tension, and that if we all just got comfortable in our bodies, we would experience collective enlightenment. Some somatic therapists will claim as much. But this is obviously not true: we are thinking creatures also, who can cause ourselves plenty of real suffering with maladaptive beliefs that are easiest to interact with on the intellectual level, not with weird shaking exercises.

But if you’ve been doing therapy for years and nothing’s moving, perhaps it’s time to ignore your head and move your attention downwards.

The Bay Area has a curse. It is the curse of Aboutness. Social life here is not regarded as something people do naturally, an organic element of being. It has to be About something. In New York, it’s an important component of the human repertoire to dress up nicely, gather, drink and eat, be part of the throng. In the Bay, most gatherings have the sweaty air of Purpose. Discussions are held to uncover new information, not because it is good to be around each other. Conversations feel like podcasts and the hosts are not funny. Someone recently said to me: “I’m tired of drinking in living rooms with overly smart people.”

Sure, you could characterize the New York social life as purpose-driven: social positioning, conspicuous consumption. But motivated beauty is still beauty. I don’t care what motives make people strut alluringly towards delicious meals, or acquire interpersonal grace. I care about the actual richness this creates. It’s what we do instead of birdsong. In New York, the attractive people are attractive, but so are the ugly people — from the West Village girls to the octogenarians, costume and posture convey points of view.

In the Bay, beauty (personal and otherwise) is looked down on and the famous gender imbalance has chilling effects. Is there a less sexual city than this? Perhaps Salt Lake, but I’d imagine it’s close. My gorgeous friend M is self-conscious about wearing pretty dresses, which is insane anywhere else, but reasonable here: hotness is a quality people aren’t sure what to do with. Recently there was a themed Gender Ratio party where beautiful young women dressed glamorously, at least one for every man. In other cities this would be referred to as a party.

The good, sweet men are scared of women. They find it unacceptable that someone, somewhere, could find out that they want sex. Meanwhile, many of the rich older men are shockingly misogynist, or keep harems. The hippie guys know how to fuck but performing the dictates of adulthood is something they’re less handy at.

An eligible young woman recently told me: “someday I hope to experience monogamy.” Multiple women in their 30s, who lived here previously, have referred to poly as a “mind virus” that ate their 20s in discussions with me, without consulting each other. Most of the women who want monogamous relationships either import somebody (my wife’s strategy) or they move away. Sometimes you’ve got to meet your husband at a gangbang. Otherwise, women date the same guy, who everyone knows is a terrible boyfriend, and all have the same experience. People who care about present-moment phenomena, who don’t need to be here for career reasons, eventually move away. Crowds feel dead. Nobody is noticing each other. Bodily information doesn’t ripple from person to person, communication below the neck is limited.

The sexual dynamics themselves are not relevant to me personally. What’s relevant is that a place so erotically damaged has little eros, generally. Culture springs from the willingness for romance. Without it, life is less directed by wonder and attraction writ large. Fewer connected conversations with people who laugh easily and palpably enjoy each other’s company. Fewer moments when it feels like the human burden has been lifted (those moments are the inverse of Aboutness).

People are dreaming up the future here, who have never fully experienced their own bodies or emotions. They talk philosophically about how to reshape society, but don’t know what society feels like. They’ve never been able to rely on peers, or receive care informally. San Francisco is an avoidant city, and Berkeley is an anxious colony. The most awkward people I’ve ever met write widely read posts about the secrets of charisma and attraction. Psychology is one topic haunting the city here, because so many have a rough go of it. But the main topic is, of course, AI. A friend’s group house had “days since AI mentioned” as a counter written on the whiteboard, I never saw the number rise above 2.

I met a guy recently who might be starting a cult. He gave me some ideas about how to align corporations with real human interests. Obviously he had never heard a critical response to his positions, which were silly. There really are so many cults, and they’re all mediocre NXIVM cover bands. Human potential, what if we unlocked everyone, what if we finally cut off the shackles that stop us from being perfect. The common view is that humanity is a problem which can be solved if we finally just put our heads together. Lots of the most brilliant people I meet out here were once cultists. It’s the local version of pledging a frat. What I’ve concluded, after surveying many of the groups, is that the only people worse at organizational design than hippies are nerds.

It’s a good place to work, to meditate, to experience solitude. I’ve grown more intellectually rigorous, because everyone here is so fucking literal-minded. My cardio is better because I can run along the ocean, next to a cluster of trailers parked by Emeryville, a topiary-ish mall-oriented suburb. There is a miscreant violinist there who watches me huff and puff. It feels so good to be alone with God in the kelp smell in the green of early evening. I’m happy and fulfilled here as long as I behave like I’m living in a rural setting, with calm, quiet, and a few dear friends for an occasional dinner.

And then I return to the people and the smell of Aboutness greets me again. Sure; I am describing a pair of bubbles: the tech and spirituality cliques. You can live outside of those bubbles — at which point, you are in a 2nd-tier American city, which is to say, living one of the best lives possible in material terms, although without much of a shared social fabric. Snail Bar is a fun night out, the Flour + Water pasta tasting menu is great, Royal Egyptian Cuisine is one of the tastiest lunches of my life. It does feel thin. Over and over again, I meet people who have moved here a few months ago. They turn to me and say something like: “I heard that the Bay was amazing. Is this it?” If I feel like being encouraging, I mention the natural beauty, of which there is an embarrassing supply, enough cliffs and gardens for a lifetime of rumination.

An old friend told me “it sounds like you have insufficient bullying there,” and that is a reasonable diagnosis of everything good and bad about the Bay. And yet, I hesitate to write this piece, because it feels a bit like bullying, but nowhere near sufficient. I do love many of the individuals here, so many. Truly love. There is a mutant species here that is scarce everywhere else. I just don’t like the gestalt that forms around them. The Bay sucks up bright minds and invites them to descend into insular parody. It also sucks up try-hards who imitate the genuine eccentrics and, in the process, merely become mediocre dysregulated people. So what is the cure? I hear there are plans to import 50,000 art hoes. Unless imprisoned I believe they would blow away to LA within a season. It could help to implement Parisian sidewalk drinking culture. Just put people on the sidewalk facing each other, and give them natural wine that tastes like pickles and $26 fish crudo.

Ultimately, Aboutness may not be curable. It is just one manifestation of the local spirit. This place has always been transient and searching. From the gold rush to the dot com bubble, to Philip K. Dick’s amphetamine-fueled visions, this is where the future has repeatedly almost solidified. Maybe the Bay Area will always find itself tomorrow.

Thank you to Cate Hall, Carly Valancy, and Sarah Sherman for helpful feedback.

Because of course the absolute opposite is true. I’ve tried so hard to learn how to connect with people. It’s all I ever wanted, for so long. I can still remember the pain of my youth, when the brightness of my experience felt like a wasted gift, a rude excess, without anyone to meet me in it. And I remember how many years of deliberate practice were required to secure routine pleasant interactions with my fellow human beings. I was born without social awareness, and I installed mine bit by bit.

Looking back, it’s clear to me now that my increase in social skill wasn’t linear, like building a little more strength with every trip to the gym. Instead, I had six different paradigms of connection — six entirely different ideas of how to approach people — that I moved through on the way to my current method.

1: Connecting with people is about being a dazzling person

As a child, I was abrasive and abrupt, excitable and sensitive. Interacting with me was exhausting. And my position in the hierarchy reflected it. I was probably the most severely bullied kid at my school, because I was one social notch above children who were so pitiable it would be rude to mock them.

In early adolescence, not much had changed. My closest friends were the hosts of This American Life, which I discovered through a webcomic about video games. On first listen, I recognized that the adults on that show were unlike me. They were witty and urbane, confident but self-deprecating. And, since I adored them, I figured that to be adored, I should be like them. Thus, I determined that I would fashion myself into an interesting person to listen to, and this remained my approach throughout most of my undergraduate education.

Thus, in my teens, during/after a spell of playing the ukulele in public to attract attention, I:

• Memorized poetry and read difficult modernist novels

• Got good at telling dramatic stories about my life

• Developed opinions about scholarly subjects, like Roland Barthes, Werner Herzog, and so on

In essence, I became an example of obnoxious precocity, a heartfelt young wordcel.

This earned me a bit of approval. But the approval was polarized. My act only worked on those who valued a particular kind of cultural intelligence — everyone else just found it tiring. And even when it worked, which it did chiefly on campus, it was distancing. There was a presentational quality to my interactions, which limited the possibility of real dialogue. At the time, I could see that I wasn’t yet one of the gang, but couldn’t see why. I was demonstrating my erudition: surely that was enough to be inducted into the ranks of the socially accepted?

The limits of my approach, and how to move beyond it, only became clear when I worked in restaurants.

2: Connecting with people is about playing their game

After becoming NPR-ish in college, I went insane for a bit. Like, real mental illness, dark night of the soul, wandering the streets muttering to myself, constant suicidal urges.

When I recovered, I found myself working as a busboy at a high-end pizza restaurant, where I was being considered for promotion to the rank of bartender. I’d become capable at making coffee and cocktails, but my social skills were considered unacceptably poor. I overheard one of the bartenders, who felt I shouldn’t be promoted, discussing me with the manager: “He talks in paragraphs,” was the complaint.

Aware of my deficits, I started studying the servers who were socially admired. And I started noticing that they operated in a completely different paradigm from me. Some of the servers, who were decent, did what I did — they presented a fixed role, a plausible bit, like “extravagantly gay man with quips,” or “cheerful country girl.” But the really good servers had flexibility. They would figure out what social game the other person wanted to play, and then they would play it with them.

If their tables ordered in a brusque and direct fashion, they became efficient and stoic in response. If their tables wanted to flirt and banter, the servers would animatedly yes-and whatever came at them. They were responsive — they weren’t looking to shore up a preexisting identity, so much as they were simply open to play.

Although adopting this approach required practice, I instantly recognized it as superior, and took to it devotedly. After a year of this, my manager said to me: “you’re never going to be my top salesperson. But you make people ridiculously comfortable.” It can be easy to change your personality when it’s organized around achieving a goal, and you realize your previous strategy isn’t going to work. Also, restaurants are a great arena for trying on a new persona, given that every new table is another opportunity for novel behavior.

I started feeling like I was pretty charming, and this was true, relative to my standards. However, when I moved to a restaurant with more seasoned servers, I learned that I was still a beginner.

3: Connecting with people is about loosening your grip on the game

I transitioned into a fancier, nicer restaurant, in a cooler neighborhood, where I was, again, the awkward kid. I was now surrounded by real adults who were really urbane and charming — career servers who had spent over a decade refining their social procedure.

There was one in particular who captivated me. Compared to the others, he was messy. He forgot orders, recommended weird pairings, and sold tables on entrees that the restaurant had stopped serving a month ago. Nevertheless, everyone loved him because of his incredible social skills.

But they were weird incredible social skills. He constantly said things that didn’t make any sense. “Let’s go home,” he’d say, as a greeting. “Lovely ball,” he’d say, as an assessment of quality. There were dozens of other catchphrases and odd habits. Somehow it worked. I watched everyone adore him for some time, me included, while feeling incomprehension re: how this effect was being achieved. What I started to realize was that his surreal quirkiness was sending out an unspoken message, something like: “I’m not a real server. This isn’t a real restaurant. All of these social roles we’re inhabiting are just fictions. We can all just relax.” His odd, uncontained manner gave permission for everyone else to escape containment in a collective jailbreak.

I adopted this attitude in my own way, tacking on bits of benign strangeness to my interactions. Whenever I offered water to tables, I said it in an odd, skeptical way, as if I’d just become lucid in a dream. “Hi…,” I said, while making direct eye contact. “Can I get you some… water?” I’m not exaggerating when I say that about 95% of my tables loved this instantly. By being awkward on purpose, I became their relatable comrade, rather than an impersonal representative of a snobby establishment.

Previously, I’d thought there were two choices you had with a social script: reject it, or go along with it. But I started developing an instinct for a third choice: how to take the other person sideways, into the weirdness of open possibility, where it’s not clear how anyone should feel, and there are no requirements.

For example, I once spilled a bottle of olive oil onto a woman’s lap. She happened to be wearing an exquisite blue designer suit. I looked her in the eye, and I could recognize that she was about to be angry. A reaction was forming on her brow, like a looming cloud. In the brief moment before thunder struck, I said: “Sorry, I was just distracted… by how special you are.” She paused, startled again. Then she broke into a huge smile, laughed uproariously, and grabbed my hand with both of hers. We looked at each other for a moment, silently, and the rest of the table also watched, unsure of what to think. “Send us the dry cleaning bill?” I said. “Sure thing,” she said. I nodded and ducked out, leaving it there. It was someone else’s table, and the server reported that she received an unusually large tip.

This penchant is still a large part of my conversational habits. Much of what I say, in casual chit-chat, is directed towards loosening the grip, rather than conveying anything in particular. This inspired a blog from my wife about how some people communicate in order to exchange facts, and some communicate in order to find connection:

This didn’t click as an explicit model for me until recently. What did it was hearing my husband, again and again, say things to people that made me cringe because to me they sounded hostile or disingenuous. And again and again, I was confused when people’s reactions to him were almost universally positive. Clearly, the issue was that I was lacking some essential piece of human software, not his sense of propriety. Now, I’m not a total dolt — I’m familiar with the classic wisdom that a large proportion of communication is non-verbal. I can read body language quite well, thanks to deliberate study as a poker player, and I know to smile, send out friendly vibes, mirror the other person, all the things you can read in a book. But until I watched Sasha in action, and we tried to analyze my hang-ups, it really didn’t sink in for me just how much less important what you say is, to most people, than how you say it.

It is gratifying to me that this lesson propagated through space and time from an Italian restaurant a decade ago to a recent Substack post.

However, after I learned this trick, there were still a couple of major updates yet to go.

4: Connection is about dancing to the music

I quit fine dining to be a roving freelance journalist, then achieved my childhood dream of becoming a published author. It did not make me happy.

I then entered the classic California pipeline: when worldly pleasures fail you, attempt to locate the happiness without conditions. I became a self-therapy and meditation nerd, and, as a result, I achieved a much greater level of embodiment. I realized that I’d been stuck in my head for my whole life — that this is not a figure of speech, but a real description of how your subjectivity is very different when you’re uncomfortable with emotion, and living behind the sensory filter created by a rigid self-concept.

Bam! I was plunked into the vivid depth of bodily expression. There was so much I’d missed before. Though I was verbally skilled from my restaurant training, sometimes my timing was off, because of all the delicate non-verbal signs hidden from me. It was not unlike a colorblind person, unaware of their condition, suddenly seeing the whole rainbow.

There were these new, subtle flavors of human presence in front of me, like:

• The bitter-edged weariness of a person who feels underpraised

• The wary stiffness of a man in charge who feels insecure

• The speed of a nervous intellectual trying to dance around their emotions

• The languid tones of someone presenting themselves as a sexual option

• The leonine nonchalance of real confidence

I started seeing new subtleties in people I’d known for years. It was like I got to meet everyone again.

Before this, I’d interacted with people who seemed psychic. They could pick up on delicate undercurrents of my state that I wasn’t even trying to communicate, or befriend me instantaneously by giving me exactly the kind of attention I wanted. And now I thought: oh, this is how you become psychic. You just fucking look at what is happening on the faces and bodies of other people.

With this new perspective, connection felt a lot more like dancing. If I stopped to think about the information I was getting through body language in real time, then my communication became leaden. But if I simply reacted, from a state of fascinated absorption with the physical data in front of me, somehow it typically worked out okay.

This could have been where it ended, but Twitter, that beautiful scorpion, changed the trajectory of my life again.

5: Connection is about projecting love and acceptance

Flash forward to 2021. I’d started working as a writing coach during the pandemic. I didn’t have much coaching experience, so I didn’t yet know what my style was. And I was living in the desert in a decaying marriage, which made me feel experimental. “How did I get here” is a question that sometimes enables a mood of “and where else could I go?”

I stumbled across a tweet by Tyler Alterman, talking about how he had managed to get autists to successfully do energy healing simply by earnestly pretending to be energy healers. And I thought, “alright, fuck it, I’m going to pretend I can heal people with my energy.” I had no illusions about the truth of this, but I wanted to take it on as a useful fiction, to see what would happen.

I thought about people I knew with an energy I’d described as healing. There was something they had in common, maybe. A nonjudgmental, velvety openness, an alertness without a sense of problem. Perhaps I could try that.

I’ll always remember the first call I took in this mode. I slipped into a groove that I was familiar with from Zen meditation, a place of spacious openness, luminous awareness. Rather than trying to get to the bottom of the issue, I just focused on being in that state with my interlocutor.

They had a moment of tremendous emotional catharsis, complete with full-body sobbing, and thanked me for opening their heart. And I was like, for opening what now? I didn’t do anything except relax and gaze softly and ask a few questions. This doesn’t make any sense.

After a few similar occurrences happened, I learned a couple of things that seem, in retrospect, obvious:

• A large-ish amount of the action of therapy/coaching is simply having nervous system capacity for someone in distress.

• Many people are desperate to be listened to because so few people listen, so if you go around your life in a state of presence and openness, you will be treated like an oasis in the desert.

• If you meditate long enough to react to the world with loving gratitude, people can really feel that.

It seemed like a prank, overall. Connection was impossibly scarce when I was a kid. Then, it became something I could obtain through a delicate social dance. But after this paradigm shift, I learned that if I just threw myself open, other people would do all the work.

Sure: it took me a lot of intentional self-renovation to equip myself to do this trick. But once I did, it was easy. And potent. I started hearing phrases like this a lot: “I don’t know why I just told you that, I’ve never told that to anybody.” It was shocking to find instant intimacy with what felt like anyone, anywhere — whether it was the schizophrenic son of a cactus store owner, or, after I got a divorce, a first date with someone I didn’t even have that much in common with.

But there are upsides and downsides of making your whole life into a connection-fest.

6: Connection is something I can take or leave

There are two reactions that one could have to the previous section. “Wow, that’s cool, how he developed the ability to create a lot of deep connections in this lonely world.” And: “that is a weird and creepy thing to want, sounds kind of vampiric.” I believe that both reactions are correct in some proportion.

Here is the thing about going around the world in a state of emotional openness and presence. Many people are hungry for that kind of attention. They might dream of getting it from a parent, or a mentor, or a lover, but might never receive it. Maybe never in their lives. And if you just walk up and give it to them, for free — but you aren’t actually interested in a deep relationship — then they might, rightfully, feel manipulated, or at least confused. You are writing them emotional checks you can’t cash.

Because… what? You want more connection? Why do you need that, right now? Can’t you be comfortable on your own? These are questions I started asking myself when I realized that my whole life was becoming a therapy session. And I also realized that, even in a therapeutic conversation, going right for maximum emotional connection was rarely the most productive move.

Around this time, I’d started dating my now-wife, and we decided to be monogamous. In a classic moment of Cate candor, she said to me, without a hint of anger or judgement, something like: “it seems like a lot of women have crushes on you. I don’t think you have bad intentions, but this must be a product of something you’re doing.” And, in fact, it was; I was going around dangling the possibility of emotional connection indiscriminately, ignoring the fact that it’s entirely reasonable to interpret this as flirtation.

So I resolved to moderate my approach, to slow the whole gooey business down. I settled on a goal: to consider connection as a dial going from 0-10, and to be comfortable with any setting on that dial. And, rather than always pushing things in the direction of connection, I resolved to follow my conversational partner’s lead. Someone wants to have a four-hour bonding conversation at this house party? Sure, let’s do it. Someone wants to say “let’s get it” and literally nothing more before we spar in jiu-jitsu class? I also want to interact in that mode, and to consider each human interaction equally informative and worthy of attention.

I chilled out. And by that, I mean I:

• Meditated for hours in float tanks, to train myself to enjoy deep presence completely on my own

• Read a bunch of stuff about anxious attachment, and tried to nudge myself in the direction of secure

• Tried to deeply accept feelings of solitude, which led to a life-defining mystical experience

It’s been a couple of years since I set my personal goal, and I’ve mostly achieved it. I routinely have interactions that are achingly rich with emotion, but also conversations that skip merrily on the shining surface of pleasantry. I’m told that I can come off as standoffish, and sometimes a little bit intimidating, which is welcome news.

Perhaps now, I am finally socially normal.

Thank you to my darling Cate Hall for input on this piece. Credit for the image goes to Dan Allison.

Let’s call them Bouba and Kiki spirituality. We could also call them mommy and daddy spirituality. The alert observer notices that they map onto the anxious/avoidant attachment dichotomy. Bouba spirituality charges fully into the lusty swelter of biological existence, urging union as a recipe for the disappointments of life. Kiki spirituality sees restraint and perspective as the recipe for contentment, stepping back from the wheel of samsara rather than spinning it better.

Bouba spirituality’s poet laureate could be Wallace Stevens: “Beauty is momentary in the mind, the fitful tracing of a portal, but in the flesh it is immortal.” Kiki spirituality doesn’t necessarily venerate poets, but might admire this line of Robert Lowell: “The Lord survives the rainbow of His will.” The mascot of Bouba spirituality is a sexy earth mother who makes a mere glance feel like a deep embrace. Kiki’s mascot is a white-haired ascetic who composes the chaos around him via his unflinching nature. Bouba says: the universe is built on love, so would you like a hug. Kiki says: sure, but the Godhead’s love is quite unlike your temperamental longings.

My favorite teachers straddle the two categories. Stephen Snyder, for example, instructs his students to meditate on both the Manifest and Unmanifest Absolute — the former is love and light, the latter is potential and stillness. I wish I’d followed him when I was 20, instead of following my own stupid inclinations. These inclinations ran me right into the dead end of Kiki.

Like so many other young men, I saw the Zen path as a sure method of wiping out that loathsome inconvenience, my personality. I believed that I could rise above my own messiness if I practiced inner deadness. This works, ish; if you steadily furrow your brow against your impulses, they eventually become sluggish. If you’re as chaotic as I was, this might even be an improvement over your baseline mental state. The issue is that this forced equanimity typically doesn’t last — the indignities of life will eventually break you open.

I spent some time soaking in the dead end of Bouba spirituality more recently, after I’d returned to meditation with a healthier attitude. I discovered the sumptuousness of loving-kindness, the deliciousness of walking around the world in a state of uncontracted appreciation. But, ultimately, I wasn’t falling in love with all of life — just the portion of it wearing my favorite lipstick. I was trying to avoid the appreciation of solitude and separateness, which are inescapable parts of the human condition. I was accepting creation so long as it consented to be my vending machine. Existence tends to resist this approach, either by upping your pleasure tolerance or cutting you off through a bereavement.

As a practitioner, if you go full Bouba, you will ingest a garden of delights, discover the orchestral complexity of emotion, and learn that the recommendations of your gut are often surprisingly effective. This will be a revelation if, like so many bright children, your whole personality was built on shame and self-censorship, and progressive estrangement from everything below the neck. But if you follow the logic far enough, you will become a self-indulgent baby. You will reject sensible thoughts just because they don’t feel good, endlessly entertain your tantrums, and wonder why another intimacy workshop has left you dry. In the end, you really can’t out-grasp the pain of grasping.

Meanwhile, if you go full Kiki, you will float above the vibratory diversity of consciousness, perceiving how all phenomena are movements of the same energy. This will give you tremendous clarity of mind, along with a robust appreciation for awareness as such, regardless of its contents. But if you follow the logic far enough, the self you’re trying to master will burst out sideways, in petty grudges and abrupt violations of your vaunted ethical code, and you will also be a dead-eyed weirdo with a stick up your ass, unable to engage with the reality you’ve sworn to redeem. You’ll fail to notice that you’re just trapped in another kind of grasping: vibhava-tanha, the craving for non-existence.

I notice that, often, people have breakthroughs on the spiritual path when they switch sides. The analytical vipassana nerd one day plays with “remember that God loves you” as a meditation prompt, or realizes that it’s nice to break down crying in the arms of a lover. On the other hand, perhaps the connection-loving hippie, weary of all the fun they’re having, runs smack into the question of “who is really having these desires.” Those who are Kiki-biased can learn that passion is a form of vision. Those who are Bouba-leaning can learn that peace is more pleasurable than the covetous can possibly imagine.

Bouba spirituality is more affable and relatable, and it’s the one I’d pick, if I had to just pick one. It will make you a lovely cocoon for your self-structure, filled with scented cashmere throws, stacks of well-inscribed journals, and the echoes of sincere conversation. But without the Kiki side of spirituality, you will find that when your simple yearnings are catered to, they will only be replaced by more fanciful yearnings. You won’t realize that the cocoon is actually a deathbed for your ego, and while it’s nice to decorate your deathbed, eventually you have to lay down and die.

Thank you to Wystan for your input on this piece.

I think everyone needs to work out their own particular answer to this question. But in the interest of cultivating the virtue of vision, here’s my current idea of what a grownup is. As with the marriage post, I’d like to emphasize that this is the high standard I’m aspiring to, not a statement about who I am able to be consistently.

If you’re a grownup, you:

> Know what game you’re playing and endorse it with open eyes

Fine to be a bachelor poet chasing your heart through seaport bars and desert highways. Fine to be a family man who is neurotic about hiring the exact right babysitter. Fine to be a girlboss, fine to be a tradwife. As long as you understand the game you’re playing, your motives for playing it, and its likely effects on the world, and endorse it given the information you have.

> Can work with your opposite energies

If you’re independent, have you owned up to your needy dependent squishy parts? If you’re an empath with big watery eyes who loves merging with people, can you take care of yourself? If you’re a serious type A high-achiever, what’s your relationship like with play? If you’re a clownish sort, can you see the virtue in taking one or two things seriously?

> Understand why things are happening

There is a certain age at which it stops being cute to constantly say, “Why does this keep happening to me?” Because you are causing it to happen. Try to understand how you engineer the repetitive occurrences in your life. Do not continuously run from the truth about your behavior.

> Reduce, not increase, the ambient level of drama

Some people volatilize the surrounding area, leaving behind a string of conflicts everywhere they go. Some people have a civilizing effect and help nearby conflicts reach harmonious conclusion. NB that conflict avoidance is just a form of deferring the drama with interest. Have you squashed all of your beefs, and stopped producing new ones, to the extent possible?

> Mend, rather than break, more generally

You just make the world around you better, in whatever way is currently practical, at least a little bit.

> Give and receive mentorship

In general: your excess capacity and knowledge are going to those who need it, and you’re also consciously looking to absorb what you don’t know from your elders and superiors. You’re neither excessively humble about your expertise, or shy about the fact that you still have a lot to learn.

> Have self-awareness, but are not primarily self-focused

You understand your own baggage and shadows, but your whole life isn’t about perfecting yourself, or ridding yourself of every last particle of micro-baggage. The full range of emotion is open to you, and you’re also happy to acknowledge that your emotions may not be the point of a given situation. Some sort of healthy cyclic balance between working on yourself and working on the world.

> Have some sense of the spiritual

If you don’t know what people are talking about, experientially, when they talk about God, or Buddha Nature, or whatever your favorite label is, you are missing a large part of the human experience that is importantly humbling and helpful in a bunch of other ways. You can think whatever you want about the metaphysical claims that people attach to spiritual experience — it’s totally coherent, although hard to do in practice, to have classical spiritual experiences and remain a committed atheist. But if you just have no idea what that Thing is, you’re missing a basic point of life. Once you are not missing that basic thing, there is then the tremendously challenging lifelong project of understanding how to live in alignment with it, a subject that nobody can definitively crack.

> Do not see your immediate relationships or the world through the lens of the drama triangle

Grownups are not surrounded by rescuers, villains, and/or victims to be rescued. This includes your view of society. Implied in this point is that some entire political movements are not composed of grownups, or, rather, infantilize the people who subscribe to them. I stand by that implication.

> Can basically handle your shit

Would I trust you with a baby? How about assembling something rudimentary with clear instructions to follow? Can you be counted on to keep your commitments — the important ones, at least? Have you stopped counting on the ambient goodwill of adults who are willing to pick up the slack when you bail on shit?

> Don’t confuse your impressions of people with reality

We are all doomed to only really experience people via our particular interactions with them. These interactions are shaped by the specific persona and motives we show up with. As a result, someone’s response to us might be extremely different from another response they just performed an hour ago with someone else. Those who fully get this can’t take their opinions of people too seriously.

> Maintain balance of dignity and humility

Every day, you wake up in a biosphere that manufactures just the right blend of gases required to power the sack of infinitesimal machines that is your body. You arise in a dwelling that likely wasn’t built by you, assembled with tools dreamt up by many others. If, standing atop this giant interdependent web, you credit yourself for your good fortune, you are a child. However, it is quite silly also to refuse compliments or pretend not to see your own gifts. (Credit for the concept of “dignity and humility” goes to Margo Fisher.)

Photo credit goes to William Eggleston. Thank you to Cate Hall, Catherine Olsson, and Mark Estefanos for your input on this piece.