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.

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.