Splitting Fives: The House Edge On Wonder

When society thinks the world exists to be "solved" we lose the things that make us human

Optimization is a great servant and a terrible god. When it’s your servant, it makes your life easier. It reduces suffering, prevents avoidable harm, helps you build bridges that don’t collapse and airplanes that land. But when it’s your god, it starts telling you what’s valuable…

There is a poisonous myth today that optimizing everything will lead us to the best world. When pushed to the extreme we all recognize the absurdity of it¹ and yet, just like the frog, we are being slowly boiled in a pot of over-optimization. Instead of the best world, we just get the same world. Over and over and over. The edges get slowly sanded away. The parts of life that used to be unpredictable and deeply human have the giant accusatory microscope of society pointed at them in an attempt to “cure” these inefficiencies.

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When you remove enough of this over time, you slowly scrub the soul from it. We’re better than ever at building things and yet it feels as if we’re losing the unexplainable wonder from them because we’re so obsessed with optimizing the soul out of everything.

We’re doing it politely for the most part too. Rationally, even. But precisely because of that, it’s hard to notice what it’s taking from us until you step back, look around and realize the world is becoming…flat.

Everything is technically better and yet somehow feels less alive.

I think this collective numbness a lot of people are feeling lately is because the world is becoming louder, faster, shinier but much more hollow. This is the cost of legibility. When we turn human life into something that can be evaluated at scale we start to live in narrower outcomes.

Fewer styles survive. Fewer weirdos thrive. Fewer happy accidents happen.

Interactions just feel flatter and ~the culture~ feels far too template-driven. Even our private lives begin to productize once the incentives seep too deeply into them. How often do we reach for our phones when a moment gets quiet? Is silence some kind of bug we have to immediately patch? How hard is it to stay with a thought long enough for it to even become a thought?

What seems pretty clear is that the mechanism is painfully consistent. We measure what we can measure. And sometimes this is actually what matters but a lot of times it isn’t. A lot of times it’s just the thing that is measurable.

Then we reward the thing we can measure. Money, status, engagement, clicks, watch time, conversion. Whatever.

And then people adapt to this because we are (mostly) rational humans. We’re at least rational enough to respond to incentives and we’re insecure enough to care when the room is clapping for something.

Then a meta forms around this and the tyranny of the best practice takes hold. The best way is identified and crystallized and all of sudden any deviation from this becomes a sort of tax. Weirdness becomes prohibitively expensive in many ways.

legible vs. meaningful

If you build a society that worships at the legibility altar then you eventually find yourself surrounded by people and products that are easily understood but impossible to love or that don’t evoke any kind of emotion.

Brad Pitt Started It

The first place I felt this viscerally was in the sports world. I blame Brad Pitt².

Baseball used to feel three-dimensional: every game was this weird, slow crescendo of tension. There was bunting, hit-and-runs, pitchers with quirky deliveries, specialists on the roster who were only called on for very specific situations. Then sabermetrics and Moneyball happened. It started, as many important things do, with a significant constraint: the Oakland A’s were forced to adopt a different way of building a team because they effectively had no money to spend. Now, the problem isn’t that someone brings a calculator to a sport, but the downstream effect is that after you prove the calculator works then the entire sport reorients itself around it.

Suddenly, the sport turns into a blackjack game. The strategy gets turned into a repeatable recipe and the game becomes completely devoid of any texture or style. Congratulations, the sport has been “solved” and the prize is a much worse experience. The three-true-outcomes³ MLB is objectively a worse and less compelling product⁴.

Baseball started it, but then Daryl Morey and the basketball world quickly took the baton and beat the living hell out of a dead horse. There’s a famous boxing quote that says “styles make fights”. Well, the NBA used to have a bunch of different stylistic ways to play the game and everyone leaned into the specific strengths of their roster. But once teams realized how much the three-pointer tilts the expected value of every possession, the shape of the league completely shifted. The geometry of the sport became a spreadsheet problem to be “solved”. And solved it was. The corner three is the holy site: every possession now looks the same and every team now plays the same. People will argue the game is better because the spacing is cleaner, the skill level is higher and offenses are so much more efficient. They’re right! They’re also missing the point. When everything converges toward the same dominant strategy, you lose the tension from difference. The drama doesn’t disappear because sports will always be dramatic and there will always be an emotional attachment for the people who care most about them. But there is something missing. Texture is the closest appropriate word I can think of to describe it.

I’m not saying the rise of the Warriors in the Bay Area as patient 1⁵ is directly a result of this dynamic bleeding into the technology world. But I’m not not saying that.

There’s a bit of a romance to the idea of innovation. Stories of the gang in the garage or the savant dropout. Weirdos and nerds pursuing the answer to problems that literally nobody else cared about yet. Oftentimes these people were working within the confines of some constraint (not unlike the Oakland A’s). But once this romance becomes wildly profitable the institutions form around it and systems begin to appear. No matter how well-meaning they might be, gatekeepers arrive and let me tell you, they are optimization engines. Venture capital is supposed to fund the things furthest out the risk curve. It’s literally in the name. Lately though it feels as if it’s warping into more of a sorting machine for social proof.

the year is 2030. everyone ends up in Slytherin because you now can't get a job as an Auror unless you were in Slytherin. and if you can’t get a job as an Auror, what’s the point really?

The same schools, the same networks, the same vocabulary, the same “this reminds me of..”, the same resume shapes. Now, this isn’t some evil premeditated cabal. Humans are acting rationally in the sense that you’re not typically rewarded for looking stupid, so as long as you can fund something that resembles something else, you at least can cling to the illusion of safety. But safety is a seduction and it’s how we end up with a future that looks like a linear extrapolation of the present⁶.

Novelty, almost by definition, is illegible. It shouldn’t necessarily surprise us that the weirdest thinkers, who historically play an important role in birthing new categories, are usually obsessed with something that doesn’t even have a market yet and have little evidence beyond some sort of untranslatable conviction.

One of my IRL friends is a Hollywood writer and in one of our group chats we keep coming back to how few good movies seem to be made these days. This is probably an evergreen complaint as people get older but I think it’s somewhat revealing how dominant the share of superhero-or-sequel movies is.

A quick search of Rotten Tomatoes most anticipated films of 2026 include the following:

• Greenland 2

• 28 Years Later: The Bone Temple

• The Rip (more on this in a second)

• Scream 7

• The Super Mario Galaxy Movie

• Ready Or Note 2: Here I Come

• Lee Cronin’s The Mummy

• The Devil Wears Prada 2

• Mortal Kombat II

• Star Wars: The Mandalorian and Grogu

• Masters of The Universe

• Scary Movie 6

• Toy Story 5

• Supergirl

• Jackass 5

• Minions 3: Mega Minions

And this is just for the first half of 2026.

There was a time when you could stumble into some low or mid budget movie that was kind of strange or imperfect and yet also unforgettable in some way. Maybe the director had a particular sickness in their soul or exposed a feeling a lot of the audience was experiencing but never verbalized because they thought nobody else felt it. Sometimes these films failed, sometimes they became cult classics and sometimes they became the type of movie you watched at the wrong age and then became permanently rewired by.

But the economics and distribution changed and all of a sudden the entire supply chain was optimized. Franchises and sequels are now safer (there’s that word again) than originals. I included the movie The Rip specifically because even Matt Damon recently admitted – WHILE HE WAS PROMOTING THE MOVIE – that films are becoming shittier because audiences need to be bashed over the head with plot points. This is literally the definition of stripping away nuance.

I’m not trying to say that franchises or sequels are bad (though most of them are⁷), the point is that the system rewards a much narrower set of creative risks and squeezes out the weird mid-range where so much cultural experimentation used to live.

Never Ask To See My “For You” Page

This essay could realistically be another 5k words on other areas of our society and cultural fabric that are under siege from optimization. Music now feels like it’s grabbing your collar begging you to please, please don’t skip! The intros are shorter, the hooks show up faster, every song feels like it’s within the same bpm range. The playlist era means the skip button is just one thumb away and so naturally songs will adapt to this new reality. Now that this is a global competition too, it means artists are often seeking the greatest surface area and learning to be immediately legible to an audience. I think being immediately legible comes at the cost of creating art that changes people slowly. Some of the most impactful art I’ve experienced did not immediately resonate with me: it was uncomfortable or confusing or I didn’t know how I felt about it. There was a baked-in patience that took time and was maybe expensive in that way, but it does feel like a lot of modern culture is quietly training us out of the ability to experience this.

All of these cultural shifts are of course a result of the Almighty Algorithm, either directly or indirectly. It’s the great flattening machine that we’ve all invited into our pockets to make life smoother.

Much has been said about attention: is it all we need, how do we convert it to dollars, is all press good press?

Attention is undeniably upstream of everything now. What we look at becomes what we think about. What we think about becomes what we care about. What we care about becomes what we build our lives around.

The internet used to be a weird place. We used to find things by wandering and clicking weird links and ending up in forums with horrible design. It was this beautifully inefficient maze which meant it had plenty of room for accident. That chaotic experience has been neutered into a predictable, personalized feed designed to chisel away surprise. We all now live in these little individual universes with perfect temperatures. And it’s hard to grow anything interesting in these climates.

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Everything is not ruined. But everything is converging. The range of possible experiences is shrinking toward a future of whatever is most efficient, most legible, most repeatable, most monetizable in the moment. It can still be fun of course. And many people are doing well and enjoying this world. It’s kind of weird because optimization obviously shouldn’t really feel like a villain.

But I keep coming back to how many domains of life have this same architecture now…

You can watch it happen in social media, where we learn which version of ourselves performs best and then slowly become that version until our personality hardens into a shareable archetype. It’s why being called “schizo” is a compliment in many ways, because it signals that someone’s personality isn’t static or easily bucketed. You can watch it happen in art, where creators learn what the algo likes and start making work that fits the mold. You can watch it in academia where novelty that can’t be easily justified struggles for oxygen. You can certainly see it in politics where slogans and memes outperform nuance.

The incentives are always legible and the casualties are always things like texture, variety, culture, craft.

Some things are worth doing poorly. We are humans and incredibly flawed beings. If we collectively build individual lives where every decision needs to justify itself then we’re naturally going to build a world where the same is true and then we’re all just living inside a spreadsheet. Spreadsheets are awesome tools but I would imagine they are pretty shit as homes.

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This is where I’m supposed to have an answer or a solution. I’m pretty anti people who just complain and don’t offer any coherent solution or action to fix whatever they’re bemoaning. I wish I had more concrete thoughts on what actually solves this growing problem but maybe it’s fitting that I don’t.

Perhaps a machine learning analogy (oh the irony) is an appropriate way to try to convey how we can reintroduce the rough edges back into our world. One way to understand this is through a concept from reinforcement learning which is the idea of exploitation vs exploration.

A system that only exploits becomes very good at a narrow thing and then gets stuck. A system that explores creates the possibility of discovering something better, something stranger or even something that rewrites what better even means altogether.

Cultures that explore create art movements and revolutions and new genres and a more vibrant future. Cultures that only exploit by definition ultimately create a monoculture. And monocultures are fragile. It feels like we’re in the midst of building a monoculture of taste, and of incentives and of human behavior.

And it’s making us brittle.

So to me the obvious first way to overcome this is by intentionally reintroducing exploration. This is admittedly abstract but creating “wide games” is the most direct way to do this in practice. Wide games are just environments where lots of different strategies can win and where weirdness isn’t punished by default and where the incentives don’t collapse everything into a single, dominant meta. It is poker⁸. Wide games reward variety and experimentation and human texture.

The most direct way to fight the rising tide of hyper-optimization is to build pockets of life that are deliberately unoptimized. We need spaces where we refuse to measure. I think this actually sounds much easier than it is because of how engrained measurement has become in our daily lives. There’s a pit of guilt that we feel when we’re “wasting time” but I think it’s something we need to become more comfortable with. Go for a walk without tracking our steps or without headphones. Take photos we don’t publish. Make art that never gets likes. Try a hobby that we’re terrible at for a long time. Being bad at new stuff is kind of the point in some ways. It’s one of the last remaining experiences that truly forces us to be present in a way that isn’t easily replicated. We are forced to inhabit it. It’s embarrassing almost in a cleansing type of way.

Another direct way is to use that sweet, sweet attention currency to reward weirdness. We’re all voting with our clicks and feeding the machine, so deliberately lingering on things that are not immediately legible is at least a start. Watch the weird film. Listen to the album that takes a couple tracks before it starts to make sense. Read the bookmarked essay that’s too long. I think it’s the most immediate, tangible way to create oxygen for the future.

As humans we’re truly S-tier at crafting a narrative after the fact to describe why things happened. We tell stories backwards and tend to erase some of the happenstance or weirdness that made them possible in the first place.

Jazz was not respectable at all in its infancy. It was the type of musical rebellion that made the status quo society super uncomfortable. That discomfort was part of the point.

Impressionism was mocked. Punk was easily dismissed. Early hip-hop was treated like a local nuisance until it became one of the largest cultural forces of the last half century. The personal computer was a toy for hobbyists. Bitcoin was a niche cypherpunk experiment. The list goes on.

The common thread is that these things were weird enough to be quickly dismissed by the optimization filters we now are so quick to deploy across our world. All of these things existed in the exploration space long enough to find the people and the meaning that would enable them to become real. In some ways, many of these things wouldn’t exist today had they not had some protection from immediate performance pressures.

We need more of these places because the next wave of meaningful things will look weird too. That is the nature of novelty. The future will arrive wearing clothes that look ridiculous at first.

i can’t even help trying to make this blog more legible with things like this^

How do we overcome this in the actual texture of our lives?

I think it means choosing, over and over again, to prioritize meaning. I think it means bringing back small risks first. Saying the awkward honest thing. Starting something we might fail in public at. Allowing ourselves to be inconvenient, where a lot of intimacy lives.

I think it means letting our individual taste be ours. Taste, sadly, is one of the many muscles that we seem happy to let atrophy. If we use it more then of course we will occasionally choose wrong. That is the price of being human.

I think it means building rituals that live outside of the feed. It is in some ways an active resistance against a world that wants to turn everything into a bit or into content.

I think it most importantly means giving ourselves permission to be weird. And not weird in the performative sense. Actually weird, in our own personal way.

I’m not sure there’s necessarily a broad-based or macro solution because it’s almost paradoxical to suggest that. Incidentally it feels like a coordination problem more than anything else. The incentives are extremely real and extremely strong. But if we truly want some of the wonder and weirdness back (maybe most people don’t i don’t know!) then we have to be willing to look stupid for a while. Anecdotally it seems that this giant societal pendulum that swings every few years (or decades) is beginning to stall out and we are going to start shifting back in the other direction. As much as I love the digital world, the analog one is also pretty amazing when I take the time to look.

This is a messy ending to a piece that is probably a bit too long and a bit too herky-jerky, but that feels appropriate. The world continues to push to make everything ordered, efficient, legible, “solved”. But we don’t have to consent. We can remain complicated and textured and human. I think without this intention then the whole acceleration movement brings us somewhere we didn’t mean to end up.

What would happen if we gave ourselves permission to be less legible?

Less easily understood.

Less refined.

More alive.

1. see Bryan Johnson

2. Billy Beane but same thing

3. for those unfamiliar, this is a movement that happened in baseball where everyone began optimizing for 1 of 3 outcomes (walk, strikeout, home run) because that’s what the math says to do. you may notice that 2 of these 3 result in no live action in the field of play…

4. i do not think it’s a coincidence that the peak of the 3 true outcomes (2018) coincided with the lowest attendance record in 2 decades. credit the MLB for eventually changing their rules because the sport was dying as a result

5. James Harden and the Rockets are patient zero

6. this is partly why we recently launched Reverie Grants

7. this is a personal aside that is relevant to what i’m getting at in this piece. i love the Fast & Furious franchise. it’s obviously a ridiculous series that is actually kind of the thing i’m lamenting. but it is a series that my sister and I enjoyed together when we were younger. we’re older now and even though she has 3 kids, we still make a point to see each new one together in theatres. we even drink Corona’s at dinner beforehand (iykyk). it’s kitschy and corny and ridiculous, but that’s kind of the point. is watching Fast 10 the best use of either of our times? yes, it actually is in this case.

8. you can turn the game into GTO if you want but even then there are human variables that will always exist