The useful thing about defining good design as a form-context fit is that it tells you where you will find the form. The form is in the context. To find a good relationship, you do not start by saying, “I want a relationship that looks like this”—that would be starting in the wrong end, by defining form. Instead you say, “I’m just going to pay attention to what happens when I hang out with various people and iterate toward something that feels alive”—you start from the context.

The context is smarter than you. It holds more nuance and information than you can fit in your head. Collaborate with it.

If you want to find a good design—be that the design of a house or an essay, a career or a marriage—what you want is some process that allows you to extract information from the context, and bake it into the form. That is what unfolding is.

The opposite of an unfolding is a vision. A vision springs, not from a careful understanding of a context, but from a fantasy

Anything that increases the rate and resolution of information you get from the context will help. And anything that makes it easier for you to act on the context.

A common reason we filter information and become blind to the context is that we bundle things when we think. Thinking about our career, we might think in abstractions like “a job.” But really a career is made up of a bunch of different things like a salary, an identity, relationships, status, a sense of meaning, and so on. It is often easier to find a fit if you unbundle these things, and think about the parts that matter to you individually. Do you actually need more status? Or can you find a better fit if you go low status?

Another common reason the feedback loop of unfolding often works poorly is that people have decided on a solution already. They have turned on their confirmation bias. They have decided that a certain solution is off-limits. Let’s say you are 34 and haven’t found a partner but want kids. If we unbundle this, it is clear that the problem of having a kid and the problem of love are not the same thing, so you could solve your problem by having a kid with your best friend instead. But this feels weird. It is not the vision you have for your life. And it seems dysfunctional. Observe that feeling—it is, perhaps, a part of the context. There is some information there. But to unfold, do not write off any solutions. Leave them all on the table; let them combine and recombine. Many good ideas look bad at first. To increase the rate at which you understand the context, you want to develop a certain detachment. When the context thrashes one of your ideas, you want to say, “Oh, that’s interesting.” It takes practice. But it is worth getting better at. Reality is shy—it only reveals itself to those who, like honest scientists, do not wish it to be something else.

The faster you can collide your ideas against reality, the faster you get feedback.

The school system is centered around visions, not unfolding. You are asked to make decisions about realities that are five, ten years down the line, and you get no feedback on your decisions.

you’re less torn by anxious attachments when you recognize how something must naturally and necessarily unfold.

Knowledge is freedom from getting mad at facts.

Detachment does not mean you don’t care what happens. It just means you don’t care whether a specific thing happens or not. You want to know the outcome of the coin-toss (you care), but you don’t care whether it is heads or tails even if you’ve bet on heads (you’re not attached to a specific outcome). The important thing is that something happens, which means you’ve successfully kept play going, but without keeping score.

Emotional Self-Management: I like to think of this as accepting the emotions you have instead of having emotions about having emotions in an endless stack.

Fear. Not fear, plus anxiety about fear, plus guilt about anxiety about fear, plus shame about displaying guilt about experiencing anxiety about having fear. This is emotional focus. Instead of retreating from an emotion through layers of additional emotions until you find one you can deal with, you experience the actual emotion for what it is.

But here’s a constant: each year you learn more about yourself. You see yourself in different environments, different styles of living, different communities and friend circles which reward slightly different things. You get to see yourself bend to the world around you as you evolve from one stage of life to another.

I’m convinced each of us has certain fundamental dispositions, whether they’re contained in our genes or attachment styles or Enneagram types. But we’re also prone to making up stories about ourselves, stories that we wish were true. Time is the best antidote to all our attempts at self-deception: it’s easy to lie to yourself for a day, but a lot harder to lie to yourself for a decade.

I don’t believe in the separation between thinking and feeling. I think so, I think of thinking as as an instrument. It’s it’s a it’s like, you know, it’s the intellectual psychological equivalent of like weighing scales and barometers and and rulers. It’s it’s a way of processing information. But most information is actually, like, I mean, emotional information, you know.

what makes a pro a pro and what makes a con a con? If you really dig into it all the way down, it boils down to your feelings about those respective things. And, you know, you might say things that, oh, this is objective because I wanna take that job instead of this job because it pays more. But embedded in that is the fact that you feel that that getting more money is a good thing and you’re you’re choosing to weight(?).

there’s this more abstract kind of big picture, philosophical grand thinking, which is interesting and fun, and there is there’s instrumental thinking, which is very, very functional, very, very, it’s about doing something it’s about getting stuff done basically.

the act of confronting a fear is an act. It’s something that you do. It’s something that, you know, you do with your body effectively. Even if it’s, you know, I’m gonna text my boss, right, and ask for a raise. Like, that’s still an act. It’s something you choose to do. It’s something you have an emotional response to. You feel nervous or you feel scared or, you know, you feel angry. Whatever it is, it is about your feelings and and you think to process your feelings but my cat is here. You think to process your feelings but ultimately you act.

there are quotes like the unexamined life is not worth living and then people flip it and say the unlived life is not worth examining. I think both statements are kinda true

I want the world to have more good thinkers and the way to do that is to, you know, like is to be like Richard Feynman, Feynman, I feel, which is to to enjoy thinking, to show the to show, you know, he described it as I think the the pleasure of finding things out. Right? And the pleasure of really understanding how things work. Because when you really understand how things work, you can manipulate it and how things work.

I am trying to demonstrate my own love for thinking and for processing information and for making sense of reality. And while that’s the case, there’s also a subset of people who may be overrepresented on Twitter and YouTube who kind of take that to to, almost dysfunctional degree where, you know, you decide that thinking is a good thing and then you become obsessive about it and you become kind of it it becomes like your drug. Like, and you think too much about everything.

it doesn’t make sense for me to study everything there is about audio before I start making videos. It’s I should just make a video, keep doing it until and when something goes bad, I will learn by trying to fix it. Right? That’s that’s that is a sort of practical approach to thinking. And it means, you know, being okay not knowing some things so that you can focus on knowing the things that are most consequential, most effective, most powerful.

if you spend all your time thinking, you probably should cut that shit out a little bit. You should you can probably afford to think less. You can probably afford to, you know, do like a weekly review or something and and, you know, like, live your life a little bit.

I think a lot of folks feel like you should be doing these certain things like writing the great American novel or reading the 100 Greatest Movies of All-Time when in actuality these are achievements that have no real guarantee of happiness. Unless you are truly enjoying those journeys, there is no reason to set upon them.

I don't think there is anything wrong with having hopes and dreams, but I do feel that maybe we allow those things to be excuses for not living a content life. I also think at times we hold onto old dreams that no longer serve us, instead of focusing on something new and more applicable to your current situation.

adulthood wasn't full of Ferraris and mansions, and I found out rather quickly that I wasn't going to save anyone, because I was struggling to save myself.

Non-okayness is the opposite. I’ve described it elsewhere as being “mildly disgruntled all the time.” You’re frustrated with life and with yourself. You feel like there is something wrong with you, although it’s a different problem in each moment: you’re too soft, you’re too rough, you’re too social, you’re too alone. You constantly feel like you’re in the wrong place and you “should have” done something else to avoid this situation.

I distinctly remember one of my first days back in New York after my retreat. I was on PTO so I had the day to myself, and I didn’t have much of an agenda. Usually this is enough to put me on edge: I like maximizing productive use of my time, so I make detailed schedules and todo lists. If I spend an entire day off doing “nothing”, I’ll feel really bad and frustrated with myself at the end of it.

This day, post-retreat, was not like any day I had experienced before. It felt like literally anything could happen and things would be perfectly fine. I do some work? Great. I don’t do any work? Great. I felt like I could just sit there and stare at the brick walls of my apartment all day. I felt such unbridled affection for my roommates and friends. I started reading Stephen Batchelor’s Buddhism Without Beliefs, and felt moved by every paragraph. I could read for a whole hour without the slightest urge to use my phone. And even when bad things happened—one night I was hurt by something my friend did, another night someone at a bar yelled at me—I would feel upset, and then I’d move on, and it wouldn’t spiral into an endless internal echo of “I should’ve done this, I should be that, I should do that.”

One of the things about okayness is that it entails a lot of presence, and the more your sense of presence deteriorates, the less aware you are of the fact that it’s deteriorating.

entering stable okayness is a non-voluntary inner movement. There are many outer, voluntary moves you can do to make it more likely that the inner, non-voluntary move occurs, but none of them will reliably trigger the inner move. Being in a state of non-okayness is like having an internal knot in your mind, and the harder you try to untie the knot—the more you clench and tug on it—the tighter the knot becomes.

The things that tend to nudge me towards okayness are: retreats, quiet time to myself, long walks, reading, and looking at beautiful things. The things that nudge me away from okayness are: consuming a lot of social media, socializing a ton, having a lot of deadlines. This doesn’t mean that those things are strictly bad and to be avoided at all costs. It’s just about working through your own relationship to these things — trying to figure out what it is about these things that uproots yourself sense of okayness, and address that.

One of the trickiest aspects of the inner knot is this: each time it gets tied again, it’s in an ever-so-slightly different shape, requiring a different move to untie it.

The shift that has been working for me most recently is to recognize that okayness just isn’t something I can reliably produce. And repeatedly asking myself, what is the truth of this moment, rather than trying to figure out how I can get to some other state, or some past memory or object of blame, that has nothing to do with what is going on right now.All these things are little nudges to help make it more likely that you get to okayness.

Okayness is when you feel fundamentally at ease with reality and with yourself. You feel like you are enough: there is nothing fundamentally deficient about you. You move through life with grace and fluidity. When bad things happen, negative emotions arise, and you just feel them, and then they pass, and none of that detracts from the fundamental beauty of your experience. Life feels inherently meaningful, you’re perfectly content with how things are, while also naturally gliding towards the things you want

Deep Okayness is not the feeling that I am awesome all the time. Instead, it is the total banishment of self-loathing. It is the deactivation of the part of my mind that used to attack itself. It’s the closure of the self as an attack surface. It’s the intuitive understanding that I am merely one of the apertures through which the universe expresses itself, so why would I hate that? It’s the sense that, while I might fuck up, my basic worth is beyond question—I have no essential damage, I am not polluted, I am fine.

The dominant paradigm, as far as I can tell, is that you’re basically either unwell or you’re okay, and our job is triage. You’re fucked up and depressed, so you do some therapy, and/or take an SSRI, and then you don’t kill yourself.

I would like to replace it with the following paradigm. There is a spectrum of background mental states, from “suicidal/dissociated/freaked out” to “abiding peace, happiness, and energy.” Nearly everyone can get pretty far up that spectrum. Nearly everyone can experience profound healing and become thoroughly Okay. It is your birthright.

A psychotechnology is anything that can alter your relationship with self, from mainstream talk therapy, to all kinds of meditation, to well-applied hallucinogens, to newfangled forms of therapy like IFS, etcetera.

There is no one “path,” although some traditions have clusters of practices that will make most sense taken together, just like each kind of cuisine contains an internal coherence of flavor and texture.

Find ways to bring more and more of yourself into loving awareness. Every detail of your being. The ones you like, and the ones you don’t. Especially the ones you don’t, especially the parts that most repulse you. You know, loving awareness—even if you haven’t heard the phrase before, you know what it is. Those moments of spacious, calm, thorough, tranquil connection with whatever portion of existence you’re currently exposed to, where nothing is being challenged or conceptualized, but rather is just allowed to appear, in radiant suchness, without resistance or fear. That variety of existential condition.

What it is like-Greater feelings of immersion in the world, sense of the sublime beauty of existence-Greater affection for other people, directly connected to less worrying about what they think of me-Less worrying about what type of shithead I am for not getting things done, more getting things done-Less guilt, more skillful action to repair things done wrong in the past-Easier time reaching deep meditative states, due to massive decrease in inner conflict-Everything more pleasantWhat it is not like-Mania—I am sleeping and eating and acting more or less normally, it’s just smoother and better-Lobotomization on a mood level, I am still aware of suffering in the world, and still feel sadness, it just seems less ‘personal,’ less like a threat-Lobotomization on a tactical level, being less critical of self doesn’t mean I can’t figure out what is in my self-interest-Self-absorption, I am more concerned than ever before with the well-being of others, both immediate and distant-Passivity, I feel more assertive than ever, just in different ways

A good chunk of the pain in your life, and a bunch of your maladaptive behavior, comes from conflict with the shadow, and your instinctual response—to engage more fiercely in this conflict—is exactly the opposite of what you need. If you want to move on with your life, you need to connect with and integrate your shadow or you will live in impotent inner struggle.

Stop trying to trick yourself. Understand that the maladaptive things you do satisfy your dark desires. “Having,” goes the book’s central saying, “is evidence of wanting.” Just understand why you have engineered your own despair, and admire the engineering. And then, as if by magic, you will change.If this seems confusing or unlikely or silly, that is fine. If this seems objectionable, that is also fine3. It’s just a narrative framework.

First, EK asks you to look at a situation in your life that happens, over and over again, that you don’t like.

Once your personal drama is in your mind, EK asks you to recall the sensations associated with this situation, and then try to enjoy and appreciate them.

If you have a big chunk of non-integrated shadow, what you have is a brittle self-conception. There are lots of parts of yourself that you’re constantly avoiding, and all sorts of things that happen to you that aren't supposed to. This requires vigilance. You’ve got to filter, erase, elide, and generally Photoshop your consciousness on an ongoing basis to make everything acceptable to your judgment.That filtration might have some effects on experience generally. Maybe if your mind is enforcing a heavy-handed narrative frame, some of the aesthetic properties of life go unnoticed. And maybe the complexities of other human beings are harder to perceive behind the wall of concepts you’re placing in front of them. If you could take that filter off, perhaps the world would look different, and your existence would feel smoother, more intuitive, less fragmented.

notionally, I was very self-aware. However, in truth I’d never really looked into the things I was really ashamed of—I’d just spent time mining the sort of foibles I could use as fuel for entertaining self-deprecation. In this way, I’d unintentionally been creating a semi-accurate ‘understanding of self’ that was, partially, a coping mechanism.

Like, it was so cool that I’d arranged a way to both slake my lust for affirmation and never be seen by anyone, thus remaining in safety. So ingenious how I’d permanently arranged the role of misunderstood artist for myself. It was fantastic how I could thus remain forever unknowable, unredeemable, distant, separate, but still special, praised, remarkable.

I don’t know that it’s literally true that my mind is composed of little characters with different agendas. But I’ve gotten a lot of mileage out of adopting this as a lens. Instead of identifying with my unpleasant thoughts/feelings (this is me and I hate it, I suck) or fighting them (this isn’t me and I reject it), I now try to understand them as emanations of parts of me, which I then engage with in a spirit of open-hearted curiosity.

I remembered being criticized for my poor hygiene, and, moreover, how almost every time attention was brought to my physical form, it meant that something bad was about to happen. And then I did the most cliched therapy thing of all: I gave that dirty little kid a hug and told him that it was okay. In practice, this felt like releasing tension. A healthy inner space was created between me and the dirty kid in my mind. That person wasn’t identical to me, I was not my history. Simultaneously, though, I didn’t need to reject that person, either.

Every time I’d have some sort of weird inner tension—which was often—I would try to introspect, talk to different parts of myself, try to bring myself into deeper and deeper harmony, accept whatever discordant bits of consciousness I would normally reject.

One thing about my wife is that she’s a shaman. When she sees other people in distress, she’s uncannily good at figuring out whatever frequency they’re on, and helping them surf it. This is doubly true when people are on psychedelics; she could be a legitimate psychedelic healer if she wanted that life path.So, as I spiraled out near the Lululemon, she comforted me, and asked me, gently, but firmly, “what made you want to do this today?” And I was like, I don’t know, I don’t know, I thought it would be fun. She did not buy this, and, after some more comforting, said, “Did you think that the affirmation would make you happy? Like having a lot of eyeballs on you would make you worthy of love?” I begrudgingly agreed with this line of questioning. And then she said, “what part of you needs that—can you find it for me?”

I felt unusually sure of myself. But there was still, like, stuff. Maybe twice a week I’d still think about some embarrassing moment from my past and grunt in pain. Occasionally I still caught myself frantically speculating about what I could do to ensure that I remained a lovable/interesting/worthy person.

at some point, 90% of my self-image had been repaired, and, at that point, my mind’s basic disposition changed from default self-suspicion to default self-acceptance.

I realized that perhaps the main effect of my self-loathing, in my life, had been to get in the way of how much love I could show other people. Before me, in my consciousness, in what felt like 50-foot-tall neon letters, blinked the question: DO YOU HAVE THE COURAGE TO BE AS LOVING AS YOU CAN POSSIBLY BE

through shadow work, I stopped denying large parts of myself and brought them into loving awareness. Then, I continued that work in finer detail with introspective techniques, bringing more little bits of my mind into loving awareness. Then, I attacked one of my psychological monsters with loving awareness on LSD. Then, I cleaned everything up with loving awareness on MDMA.

Repression isn’t some fanciful concept, it’s a simple consequence of psychological reward and reinforcement. Things you don’t like to think about, you think about less, and slowly they become distanced from your habitual thought patterns, until they almost never enter into your mind. Therefore, you can quite easily end up in a state where you say, “I love myself,” and what you mean is, “I love all the parts of myself that I routinely think about, but I might have some icky feelings about all that stuff that I’m not quite capable of looking at right now.” This is where, I think, a lot of people are stuck.

When we ask for Deep Okayness, we are asking for you to accept everything, wholeheartedly. It is a high bar to clear.

To have that sense of one's intrinsic worth which, for better or for worse, constitutes self-respect, is potentially to have everything: the ability to discriminate, to love and to remain indifferent. To lack it is to be locked within oneself, paradoxically incapable of either love or indifference. If we do not respect ourselves, we are on the one hand forced to despise those who have so few resources as to consort with us, so little perception as to remain blind to our fatal weaknesses. On the other, we are peculiarly in thrall to everyone we see, curiously determined to live out—since our self-image is untenable—their false notions of us.

At the mercy of those we can not but hold in contempt, we play rôles doomed to failure before they are begun, each defeat generating fresh despair at the necessity of divining and meeting the next demand made upon us.

It is the phenomenon sometimes called alienation from self. In its advanced stages, we no longer answer the telephone, because someone might want something; that we could say no without drowning in self-reproach is an idea alien to this game.

Every encounter demands too much, tears the nerves, drains the will, and the spectre of something as small as an unanswered letter arouses such disproportionate guilt that one's sanity becomes an object of speculation among one's acquaintances.

To assign unanswered letters their proper weight, to free us from the expectations of others, to give us back to ourselves—there lies the great, the singular power of self-respect. Without it, one eventually discovers the final turn of the screw: one runs away to find oneself, and finds no one at home.

I had not been elected to Phi Beta Kappa. This failure could scarcely have been more predictable or less ambiguous (I simply did not have the grades), but I was unnerved by it; I had somehow thought myself a kind of academic Raskolnikov, curiously exempt from the cause-effect relationships that hampered others.

In brief, people with self-respect exhibit a certain toughness, a kind of moral nerve; they display what was once called character, a quality which, although approved in the abstract, sometimes loses ground to other, more instantly negotiable virtues. The measure of its slipping prestige is that one tends to think of it only in connection with homely children and with United States senators who have been defeated, preferably in the primary, for re-election. Nonetheless, character—the willingness to accept responsibility for one's own life—is the source from which self-respect springs.

Robert Pirsig’s definition of Static and Dynamic Quality:Our language is an imperfect instrument created by ancient and ignorant men. It’s an animistic language that invites us to talk about stability and constants, about similarities and normal and kinds, about magical transformations, quick cures, simple problems, and final solutions. Yet the world we try to symbolize with this language is a world of process, change, differences, dimensions, functions, relationships, growths, interactions, developing, learning, coping, complexity. And the mismatch of our ever-changing world and our relatively static language forms is part of our problem.

Words can only approximate Quality, but never fully encompass it. A static thing can never fully capture a dynamic thing.

We create problems for ourselves by using static language (e.g. judgements) to capture a reality that is dynamic & ever changing — by mixing observations and evaluations.

The caveat to keeping your identity small is when you want to identify as a positive trait – “I’m a kind person” – so that you’re forced to live up to it, especially when this is an unchanging desire.

Gatekeepers could see themselves not only as talent hunters for their own organization, but also as managers of society’s collective supply of ambition. We could demand that they consider it a responsibility to waste as little of their applicants’ ambition as possible. That they strive to redirect and allocate that ambition wherever it is most needed.

In practice, there isn’t any single solution. Rejection is a facet of life, and everybody needs to figure out their own strategies to cope with it. The most I can offer is that it’s better when you’re aware of how it works. It isn’t enough to know, on an abstract level, that rejection is typically random and impersonal — but it helps.