Taste has historically been reserved for conversation about things like fashion and art. Now, we look for it in our social media feeds, the technology we use, the company we keep, and the people we hire.

When I ask people what they mean by “taste,” they’ll stumble around for a bit and eventually land on something like “you know it when you see it,” or “it’s in the eye of the beholder.” I understand. Words like taste are hard to pin down, perhaps because they describe a sensibility more than any particular quality, a particular thing. We’re inclined to leave them unencumbered by a definition, to preserve their ability to shift shapes.

’ve found a taste-filled life to be a richer one. To pursue it is to appreciate ourselves, each other, and the stuff we’re surrounded by a whole lot more.

I can’t think of a piece of writing that does this more effectively than Susan Sontag’s “Notes on ‘Camp.’” In her words, “a sensibility is one of the hardest things to talk about... To snare a sensibility in words, especially one that is alive and powerful, one must be tentative and nimble.

Things don’t feel tasteful, they demonstrate taste. Someone’s home can be decorated tastefully. Someone can dress tastefully. The vibe cannot be tasteful. The experience cannot be tasteful.

Someone could have impeccable taste in art, without producing any themselves. Those who create tasteful things are almost always deep appreciators, though.

we typically talk about it in binaries. One can have taste or not. Great taste means almost the same thing as taste.

They’re the people you always go to for restaurant or movie or gear recommendations. Maybe it’s the person you ask to be an extra set of eyes on an email or a project brief before you send it out.

It requires intention, focus, and care. Taste is a commitment to a state of attention.

As John Saltivier says in an essay about building a set of stairs, “surprising detail is a near universal property of getting up close and personal with reality.”

To quote Susan Sontag again, “There is taste in people, visual taste, taste in emotion — and there is taste in acts, taste in morality. Intelligence, as well, is really a kind of taste: taste in ideas. One of the facts to be reckoned with is that taste tends to develop very unevenly. It's rare that the same person has good visual taste and good taste in people and taste in ideas.” The sought-after interior designer may not mind gas station coffee. The prolific composer may not give a damn about how they dress.

Taste in too many things would be tortuous. The things we have taste in often start as a pea under the mattress.

it is often formed through the integration of diverse, and wide-ranging inputs. Steve Jobs has said, “I think part of what made the Macintosh great was that the people working on it were musicians and poets and artists and zoologists and historians who also happened to be the best computer scientists in the world.”

taste gets you to the thing that’s more than just correct. Taste hits different. It intrigues. It compels. It moves. It enchants. It fascinates. It seduces.

Taste honors someone’s standards of quality, but also the distinctive way the world bounces off a person. It reflects what they know about how the world works, and also what they’re working with in their inner worlds. When we recognize  true taste, we are recognizing that alchemic combination of skill and soul. This is why it is so alluring.

many snobs (coffee snobs, gear snobs, wine snobs, etc.) often have great taste. But I would say that taste is the sensibility, and snobbery is one way to express the sensibility. It’s not the only way.

If rich people often have good taste it’s because they grew up around nice things, and many of them acquired an intolerance for not nice things as a result. That’s a good recipe for taste, but it’s not sufficient and it’s definitely not a guarantee. I know people that are exceedingly picky about the food they eat and never pay more than $20 for a meal.

creating forces taste upon its maker. Creators must master self-expression and craft if they’re going to make something truly compelling.

artists are more sensitive. They’re more observant, feel things more deeply, more obsessive about details, more focused on how they measure up to greatness.

Picasso remarking that “when art critics get together they talk about Form and Structure and Meaning. When artists get together they talk about where you can buy cheap turpentine.” Taste rests on turpentine.

the process of metabolizing the world is a slow one. Wield your P/N meter well, take your time learning what you find compelling, and why. There are no shortcuts to taste. Taste cannot sublimate. It can only bloom. To quote Susan Sontag one last time, “taste has no system and no proofs. But there is something like a logic of taste: the consistent sensibility which underlies and gives rise to a certain taste.

People pay you for doing what they want, not what you want. But there's an obvious exception: when you both want the same thing. For example, if you love football, and you're good enough at it, you can get paid a lot to play it.

it's clear that Bill Gates truly loved running a software company. He didn't just love programming, which a lot of people do. He loved writing software for customers. That is a very strange taste indeed, but if you have it, you can make a lot by indulging it.

If you want to make a really huge amount of money — hundreds of millions or even billions of dollars — it turns out to be very useful to work on what interests you the most. The reason is not the extra motivation you get from doing this, but that the way to make a really large amount of money is to start a startup, and working on what interests you is an excellent way to discover startup ideas.

Many if not most of the biggest startups began as projects the founders were doing for fun. Apple, Google, and Facebook all began that way. Why is this pattern so common? Because the best ideas tend to be such outliers that you'd overlook them if you were consciously looking for ways to make money.

there's something like a midwit peak for making money. If you don't need to make much, you can work on whatever you're most interested in; if you want to become moderately rich, you can't usually afford to; but if you want to become super rich, and you're young and good at technology, working on what you're most interested in becomes a good idea again.

When you have trouble choosing between following your interests and making money, it's never because you have complete knowledge of yourself and of the types of work you're choosing between, and the options are perfectly balanced. When you can't decide which path to take, it's almost always due to ignorance. In fact you're usually suffering from three kinds of ignorance simultaneously: you don't know what makes you happy, what the various kinds of work are really like, or how well you could do them

Don't wait till the end of college to figure out what to work on. Don't even wait for internships during college. You don't necessarily need a job doing x in order to work on x; often you can just start doing it in some form yourself. And since figuring out what to work on is a problem that could take years to solve, the sooner you start, the better.

You'll become like whoever you work with. Do you want to become like these people?

If you choose a kind of work mainly for how well it pays, you'll be surrounded by other people who chose it for the same reason, and that will make it even more soul-sucking than it seems from the outside. Whereas if you choose work you're genuinely interested in, you'll be surrounded mostly by other people who are genuinely interested in it, and that will make it extra inspiring

The less sure you are about what to do, the more important it is to choose options that give you more options in the future. I call this "staying upwind." If you're unsure whether to major in math or economics, for example, choose math; math is upwind of economics in the sense that it will be easier to switch later from math to economics than from economics to math

The root of great work is a sort of ambitious curiosity, and you can't manufacture that.

We can finally define what it means for someone to be differently free from you. They are people who are playing just a slightly different game than you are. That difference makes them a reliable sources of non sequiturs in your life. Waiting for nature to present you with a parrot or a piece of corn to awaken you out of a finite game is a tricky, chancy business.

Differently free people change the equation in an interesting way. When you include a person in your life, it is because they have a definite worth (possibly negative) in whatever finite game you’re asleep in at the time. This means there is at least some overlap between their game and yours; some similarity between how you keep score and how they do. Some meaningful relationship (possibly adversarial)  between how you define winning and how they do.

This means you have a model of the person in your head. One that predicts how they will value things.

it is the parts that don’t overlap that matter. There are things that have a defined worth in their lives that are non sequiturs in yours, and vice versa. When you see through the eyes of a differently free person, you expect to see a landscape of presumptively valued things. A landscape based on your predictions of how they value things. When the other person appears to value something that doesn’t even register with you, for a moment, that thing turns into a non sequitur, a candidate parrot. It lingers just a little bit longer in your own mind than it would if you yourself saw it. Long enough that you do a double take and notice it consciously.

My alternative to the heuristic, which many of you have heard in off-blog conversations, is that I am only interested in people as long as they are unpredictable to me. If I can predict what you’ll do or say, I’ll lose interest in you rapidly. If you can keep regularly surprising me in some way, forcing me to actually think in unscripted ways in order to respond, I’ll stay interested. It’s reciprocal. I suspect the people with whom I develop long-term relationships are the ones I surprise regularly. The ones who find me predictable don’t stick around. We’re not talking any old kind of surprise, but non sequiturs. Surprises that you can’t really relate to anything else, and don’t know what to do with. Mind-expanding surprises rather than gap-closing surprises.

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.

Flirting isn’t limited to romance. Flirting is an attitude that only playful and happy people can have and enjoy. It’s the virtue of being uncommitted—to people, to philosophies, to bets. Flirting turns uncertainty, something we usually fear, into pleasure. It’s being able to take yourself less seriously. It’s being able to react to discomfort with humor. Fortune is a lady and she favors whoever makes her laugh. Most people can sting like a bee but not everyone can float like a butterfly. You can change a conversation you don’t want to have by turning your shoulder, lowering your chin, giving a mischievous smile—a gesture my mother would call “coquettish”—and asking a slightly provocative personal question. Flirting lets you turn the tables without killing the tête-à-tête.

Within maybe 10 minutes of meeting, he showed me this terrifying — to him it was probably wonderful — spreadsheet of how he accounted for every hour of the day for the last couple of years. That’s probably not even as unusual as we might think, but there was a score at the end of the thing based on whether he had spent enough hours doing the different categories of things he wanted to be doing. I don’t know if he secretly feels punished by his own system or if he feels empowered by it. There’s not really any way for me to know. My skepticism is more about that rhetoric and way of thinking of time as being offered as a solution to someone who doesn’t have control of their time — that if they controlled their time in this gridlike way, they could succeed in life. I think that person has the potential to use that way of thinking very self-punitively.

Since you mentioned kids: A couple of weeks ago, I was hanging out with a friend who has a 3-year-old, and it took us half an hour to walk two blocks. There is a way in which, as you were saying, you could view that experience as potentially boring, but you could also see that the reason we were walking slowly is that kids are looking at stuff in a weird way! It’s a way I appreciate trying to imagine. For time spent like that, the whole question of “What are you getting out of this?” would be absurd.

A life of total efficiency and convenience? Well, why? What is left if you were to make everything superconvenient? It is helpful to make certain things more efficient, but that can tip over into becoming its own end, which moves the focus away from that larger question of why.

I want to be in contact with things, people, contexts that make me feel alive. I have a specific definition of alive, which is I want to feel like I am being changed. Someone who’s completely habitual, is set in their ways of thinking and doing, that type of person is liable to see days in a calendar as being pieces of material that you use to achieve your goals. There’s all kinds of degrees between that and someone who’s so completely open to every moment that they’re dysfunctional or something, but I want to live closer to that second pole.

The same applies to writing. For example, when one topic doesn’t seem to fit a narrative structure, it often feels like a problem I need to “get out of the way”. It’s much better to wonder: “Hm, why do I have this strong instinct that this point’s related? Is there some more powerful unifying theme waiting to be identified here?”

Often I need to improve the framing, to find one which better expresses what I’m deeply excited about. If I can’t find a problem statement which captures my curiosity, it’s best to drop the project for now.

I’m much less likely to flinch away when I’m feeling intensely curious, when I truly want to understand something, when it’s a landscape to explore rather than a destination to reach. Happily, curiosity can be cultivated. And curiosity is much more likely than task-orientation to lead me to interesting ideas.

Savor the subtle insights which really do occur regularly in research. Think of it like cultivating a much more sensitive palate.

“Why is this so hard? Because you’re utterly habituated to steady progress—to completing things, to producing, to solving. When progress is subtle or slow, when there’s no clear way to proceed, you flinch away. You redirect your attention to something safer, to something you can do. You jump to implementation prematurely; you feel a compulsion to do more background reading; you obsess over tractable but peripheral details. These are all displacement behaviors, ways of not sitting with the problem. Though each instance seems insignificant, the cumulative effect is that your stare rarely rests on the fog long enough to penetrate it. Weeks pass, with apparent motion, yet you’re just spinning in place. You return to the surface with each glance away. You must learn to remain in the depths.”

Depth of concentration is cumulative, and precious. An extra hour or two of depth is enormously valuable. I reliably get more done—and with more depth—in that 6-7 hour morning block than I’d previously done in 9-10 hours throughout the day.This feels wonderful. By 2PM, I’ve done my important work for the day. I know that no more depth-y work is likely, and that I’ll only frustrate myself if I try—so I free myself from that pressureI notice that some part of me feels ashamed to say that I’m “done” working at 2PM. This is probably because in my previous roles, I really could solve problems and get more done by simply throwing more hours at the work. That’s just obviously not true in my present work, as I’ve learned through much frustration. Reading memoirs of writers, artists, and scientists, I see that 2-4 hours per day seems to be the norm for a primary creative working block. Separately, and I don’t want to harp on this because I want this essay to be about quality, not quantity, but: I think most people are laughably misled about how much time they truly work. In a median morning block, I complete the equivalent of 1225-minute pomodoros. When I worked at large companies, getting 8 done before 6PM was a rarity—even though I’d assiduously arrange my calendar to maximize deep work!. I take meetings; I exercise; I meditate; I go on long walks. I’ll often do shallower initial reads of papers and books in the afternoon, or handle administrative tasks. Sometimes I’ll do easy programming work. It’s all “bonus time”, nothing obligatory. My life got several hours more slack when I adopted this schedule, and yet my output improved. Wonderful!

no internet on my phone before I sit down at my desk. I don’t want anyone else’s thoughts in my head before I start thinking my own.

If I spend a working interval flailing, never sinking below the surface, the temptation is to double-down, to “make up for it”. But the right move for me is usually to go sit in a different room with only my notebook, and to spend the next working interval writing or sketching by hand about the problem.

Administrative tasks are a constant temptation for me: aha, a task I can complete! How tantalizing! But these tasks are rarely important. So I explicitly prohibit myself from doing any kind of administrative work for most of the morning. In the last hour or two, if I notice myself getting weary and unfocused, I’ll sometimes switch gears into administrative work as a way to “rescue” that time.

I’ve noticed that unhealthy afternoon/evening activities can easily harm the next morning’s focus, by habituating me to immediate gratification.

most of the benefit just seems to come from regularly reflecting on what I’m trying and what’s happening as a result. It’s really about developing a rich mental model of what focus and perseverance feel like, and what factors seem to support or harm those states of mind.

Sometimes I just need to execute; and then traditional productivity advice helps enormously. But deep insight is generally the bottleneck to my work, and producing it usually involves the sort of practices I’ve described here.

What is our purpose on this planet? Do we have a responsibility to one another? Who even are we?Answering those questions alone is asking a lot of a person. The easier option is to choose from the platter of social-strata-acceptable possibilities we’re presented with for education, occupation, geographical location, personality, etc, and call it a day.

if you spend all your time constantly sketching (probably quickly outdated) pictures of your thinking on the bigger questions we’ve all been tasked with answering, you neglect the actual doing that would reveal answers with richer hues

incredible opportunities are unlocked by constructing a digitally consumable caricature of yourself that makes you legible to literally anyone in the world. It’s probably the most far-ranging bat signal possible to find people who think and feel similarly to you.

There’s simply so much friction in the process of turning belief into action online — meaning that most of the time all you actually get from internet attention is internalized impossible-to-attain expectations for yourself and an extremely confused ego.

If you care about personally choosing the shape, scale, and direction of your impact on the world, you might find that playing off-the-shelf games turns out to be a remarkably risky bet. There’s just no money/time-back guarantee that any of the off-the-shelf options will continue to fit you as your desires evolve. And maybe that’s ok — but continually reinventing yourself is a tiring and time-consuming task that too often leads you away from the real “calling”-finding-and-defining work.

In my book, big things are only worth committing to if the answer to the question “would you do this thing even if no one was watching?” is an immediate and unequivocal yes

What I regret most in my life are failures of kindness. Those moments when another human being was there, in front of me, suffering, and I responded . . . sensibly. Reservedly. Mildly. Or, to look at it from the other end of the telescope: Who, in your life, do you remember most fondly, with the most undeniable feelings of warmth? Those who were kindest to you, I bet.

When young, we’re anxious — understandably — to find out if we’ve got what it takes. Can we succeed? Can we build a viable life for ourselves? But you — in particular you, of this generation — may have noticed a certain cyclical quality to ambition. You do well in high-school, in hopes of getting into a good college, so you can do well in the good college, in the hopes of getting a good job, so you can do well in the good job so you can . . . And this is actually O.K. If we’re going to become kinder, that process has to include taking ourselves seriously — as doers, as accomplishers, as dreamers. We have to do that, to be our best selves.

Do all the other things, the ambitious things — travel, get rich, get famous, innovate, lead, fall in love, make and lose fortunes, swim naked in wild jungle rivers (after first having it tested for monkey poop) – but as you do, to the extent that you can, err in the direction of kindness. Do those things that incline you toward the big questions, and avoid the things that would reduce you and make you trivial.

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.