Anyone can point at something and say it’s broken, corrupt, or destined to fail. The real challenge? Building something better. The cynic sees a proposal for change and immediately lists why it won’t work. They’re usually right about specific failure modes — systems are complex, and failure has many mothers. But being right about potential problems differs from being right about the whole.

The cynical position feels sophisticated. It signals worldliness, experience, and a certain battle-hardened wisdom. “Oh, you sweet summer child,” the cynic says, “I’ve seen how these things really work.” But what if this sophistication is itself a form of naïveté?

Cynicism comes with hidden taxes. Every time we default to assuming the worst, we pay in missed opportunities, reduced social trust, and diminished creative capacity. These costs compound over time, creating a self-fulfilling prophecy in which cynical expectations shape cynical realities.

Pattern recognition is valuable — we should learn from history and past failures. But pattern recognition becomes pattern imprisonment when it blinds us to genuinely new possibilities.

Why spend years building something that could fail when you could spend an afternoon critiquing others’ attempts and look just as smart? The cynical stance is intellectually rewarding but culturally corrosive.

The alternative to cynicism isn’t unquestioning optimism. It’s more nuanced: a clear-eyed recognition of problems coupled with the conviction that improvement is possible. Call it pragmatic meliorism — the belief that while perfect solutions may not exist, better ones do.

things are broken, AND they can be fixed; people are flawed AND capable of growth; systems are complex AND can be improved.

Here’s a more charitable reading of cynicism: it’s not an intellectual position. It’s an emotional defense mechanism. If you expect the worst, you’ll never be disappointed. If you assume everything is corrupt, you can’t be betrayed. But this protection comes at a terrible price. The cynic builds emotional armor that also functions as a prison, keeping out not just pain but also possibility, connection, and growth.

Not all domains benefit equally from cynical analysis. Some areas — scientific investigation, financial planning, and security systems — benefit from rigorous skepticism. Others — creative endeavors, relationship building, social movements — often suffer from it.

What would it look like to embrace pragmatic meliorism instead of cynicism? Acknowledging problems while focusing on solutions Learning from history without being imprisoned by it Maintaining high standards while accepting incremental progress Combining skeptical analysis with constructive action

When you feel the pull of cynicism, ask yourself: Is this helping? Is this default skepticism making you more effective or just more comfortable? Are you choosing the easy path of criticism over the harder path of creation?

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.

Brat is asking for forgiveness instead of permission, because red lip gloss and watery eyes will get a “ok, go ahead—but just this time” out of any grumpy, middle-aged parking enforcement officer.

We’re captivated by femme fatales and Bond girls. We make muses out of women like Marilyn Monroe—her breathy “Happy birthday, Mr. President” at Madison Square Garden can make us feel embarrassed, mesmerized, or even disgusted, but one thing it can’t make us feel is angry: How can you get mad at an attractive woman for showing off what she has (without admitting your own envy or insecurity)?

Brat is wearing dark sunglasses to watch men play beach volleyball.

Brat is exchanging looks with a girl friend whenever a shirtless man walks by, synchronously swallowing a smirk that could’ve wiggled out of control, then going back to the conversation.

I care about how something is written as much as I care about the plot. That’s why commercial nonfictions are like Kleenex—to be used and discarded, if used at all.

I don’t want information; I want enchantment.

Jung said that the study of the soul begins and ends with Mercury, the pagan god of merchants, profits, and thieves. He’s the Tinder Swindler. He’s Anna Delvey. He’s a trickster and a master storyteller. He’s in the Forbes-30-under-30-to-prison pipeline. The Ancients designated a deity to mischief because it is a vice to try too hard to be sincere. You’re either sincere or you’re not; one does not try to be sincere. For example, if I say, “I’m humble,” am I actually humble? What mature person has to say, “I’m mature”?

Mercury represents a kind of detachment. I’m not saying that it’s good to lie or cheat; I’m saying that trying too hard isn’t the best way to get what you want. There’s something blatantly wrong with the pickup artist, yet, there’s something not quite right about someone who doesn’t have any game. You may be a good person, but what if you’re just not fun? If you’re so smart, why aren’t you happy?

Brat is a kind of transparency. It challenges hypocrisy and shakes up complacency. Brat is a splash of brandy in the cake—a little genuine fun in polite society.

Paradoxically, you need a dose of Mercury to keep things honest. It’s why the goofiest faceless accounts on Twitter are the most genuine people in real life, or why you and your close friend use the most unserious memes to describe the darkest times of your lives.

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.

I care about people more than I care about positions or beliefs, which I tend to consider a subservient class of psychological phenomena. That is to say: I think people wear beliefs like clothes; they wear what they have grown to consider sensible or attractive; they wear what they feel flatters them; they wear what keeps them dry and warm in inclement winter. They believe their opinions, tastes, philosophies are who they are, but they are mistaken. (Aging is largely learning what one is not, it seems to me).

Criticism must serve some function to justify the pain it causes: it must, say, avert a disastrous course of action being deliberated by a group, or help thwart the rise of a barbarous politician. But this rarely occurs. Most criticism, even of the most erudite sort, is, as we all know, wasted breath: preached to one’s own choir, comically or indignantly cruel to those one doesn’t respect, unlikely to change the behavior of anyone not already in agreement.On the other hand! There persists the idea that culture arises out of the scrum of colliding perspectives, and that it is therefore a moral duty to remonstrate against stupidity, performative emoting, deceitful art, destructively banal fiction, and so on. If one doesn’t speak up, one cannot lament the triumph of moral and imaginative vacuity.

One must believe, of course, that there are abstractions worth protecting, and therefore abstractions worth hurting others for, in order to criticize; and the endless repetitiveness of cultural history seems to devalue such abstractions as surely as bad art and cliche devalue words.

The game is that every time we create a new technology, we’re creating new possibilities, new choices that didn’t exist before. Those choices themselves—even the choice to do harm—are a good, they’re a plus.

We want an economy that’s growing in the second sense: unlimited betterment, unlimited increase in wisdom, and complexity, and choices. I don’t see any limit there. We don’t want an economy that’s just getting fatter and fatter, and bigger and bigger, in terms of its size. Can we imagine such a system? That’s hard, but I don’t think it’s impossible.