True Judgment: Making Decisions With Too Many Choices
How do you find, and make, meaning when AI gives you everything? How do you make decisions out of endless AI variations? The solution isn't better algorithms, or subjectivity, but developing judgment.
My primary monitor displays four different Claude-generated positioning strategies for a SaaS client, each with compelling angles. To the right, DALL-E and Midjourney have rendered eight variations of product imagery for the same client's landing page. My laptop shows Runway's video outputs: three different B-roll sequences for a product launch, each telling a slightly different visual story. In the background, Suno plays its fifth variation of a jingle I prompted earlier, while ChatGPT has filled a Google Doc with fifteen different tagline options. Yet here I am, almost eight hours into my day and nothing is done.
I’m staring at an embarrassment of riches, paralyzed by quality options, struggling to make definitive choices. I take another sip of lukewarm coffee, my third cup of the day, and feel the familiar mixture of creative stimulation and decision fatigue—and my blood pressure going through the roof. Wasn’t AI supposed to eliminate jobs and reduce my workload?
This is the paradox I face daily when I work with AI models for marketing, sales, business growth, and writing: the very abundance that should be liberating has become a trap, where we keep seeing new ideas but there’s no forward progress. There's a constant nagging feeling that the "perfect version" is just one more iteration away, replacing creative conviction with endless second-guessing. Which version is best? When is something enough? Should you keep going or regenerate another option? We’re drowning in possibilities rather than producing meaningful work. How do you decide when something is “enough"?
We need to bring back and practice something that, in our culture and society, has been out of style, avoided, and disparaged for decades: Judgment.
I remember watching War of the Worlds and offering my take on the film, only to be interrupted mid-sentence with, "Who are you to judge?" I wasn’t commenting on a person or a life choice—just a movie. The act of judging anything at all has become socially suspect.
I’ve heard the same mantra, in different forms, for decades: You can’t judge a piece of art as either good or bad. Everything is relative. There’s no right or wrong. Don’t judge! You can’t even judge a book by its cover. At some point, in the past 70 years perhaps, the tyranny of relativism enslaved us. We began treating judgment like a character flaw rather than a necessary skill. "Don't judge" has transformed from a specific ethical guideline about prejudice into a broader reluctance to make any evaluative distinctions at all. And suddenly, everyone who judged anything was automatically a bigot of some kind. What began as misguided compassion morphed into a paralysis. We conflated the act of judgment—the ability to assess, compare, and decide—with being judgmental in the worst sense.
This wasn't always the case. For all of human history, judgment was accepted and normal. It was essential to getting anything done. The master craftsman judging when a piece was complete. The editor deciding which words stayed and which were cut. The film director choosing one take over another. The farmer determining the moment to harvest. Men and women judging each other for the purpose of finding a mate. Judgment was once the hallmark of expertise, the quiet confidence earned through experience. It wasn't arrogance, it was rooted in discernment. The ability to say "this, not that" without apology. The artist's studio used to be defined by limitations. Finite canvas, paint, film, or time. These limitations weren't constraints holding the artist back. They were signals for decision-making. The photographer with just 24 exposures on a roll of film had to choose each shot carefully. The painter with limited canvas had to decide when a work was complete. The writer facing a word limit had to make hard choices about what stayed and what got cut.
Then along came the internet and the digitization of everything.
Suddenly, a photographer could take thousands of images at virtually no cost. A writer could generate endless drafts. A musician could record infinite takes. The traditional constraints that had forced decisive moments vanished almost overnight. This expansion of options seemed like pure liberation at first. Why choose any one thing when you can have it all? Why decide when you can endlessly iterate? The mantra became "more is better," and technology was all too happy to fulfill our wishes.
Nearly two decades ago, psychologist Barry Schwartz identified this phenomenon in his work "The Paradox of Choice." His research revealed a counterintuitive truth: beyond a certain point, more options lead to less satisfaction, greater anxiety, and increased decision paralysis.
Schwartz distinguished between "maximizers" who exhaustively search for the best possible option out of all the abundance available, and "satisficers" who settle for "good enough" once their basic criteria are met. Should you maximize all your options and crank out more AI-generated anything until it becomes slop? Or should you call it when something is “good enough”? What Schwartz couldn't have anticipated was how generative AI would accelerate this paradox to the point of breaking our minds completely. Today, we face thousands or millions of AI-generated possibilities. If choosing among 30 jam varieties paralyzed shoppers in his famous study, what happens when AI can generate 300 new variations with every prompt?
What once took days now takes seconds. What once required skill now requires only a prompt. AI models open entire parallel worlds of possibilities we wouldn't have considered. It creates twelve variations when we would have settled for two. It shows us twenty different approaches when we would have been satisfied exploring three. And with each new option, it plants a dangerous seed in our minds: the perfect version is out there, just one more iteration away. Just one more prompt. One more adjustment. One more variation. When intelligence is too cheap to meter, why not ask for more of it?
The hidden costs of infinite options have become painfully apparent. Decision fatigue sets in as our brains, evolved for scarcity, buckle under the weight of abundance. We weren't designed to compare dozens or hundreds of high-quality options. Our mental energy depletes with each comparison, leaving us exhausted and unsatisfied. Every new prompt squeezes the meaning out of what you get. Most crucially, natural endpoints have dissolved. There used to be a moment—physical, temporal, or intuitive—when a creative work was done. The final brushstroke. The last edit. The moment when instinct said, "This is complete." Those moments have become increasingly elusive, replaced by an infinite horizon of possibilities. Without the scaffolding of limitation, we're left to our own devices to determine when enough is enough. In a culture that has systematically devalued judgment for decades, our ability to judge is deformed and, for many, destroyed.
The crisis isn't one of creation but of selection.
Not of creativity but of decision.
Not of imagination but of commitment.
We don't need more options, we need better ways to choose between them. We don't need more variations, we need stronger convictions about which ones matter. What we need, more urgently than ever, is to reclaim the lost art of judgment. And we recover judgment by developing something I call “Threshold Intelligence”.
After staring at the twenty-third variation of a landing page design, something clicks. It's not perfect—nothing ever is—but something about this version feels right. Not just adequate, but meaningful. You've crossed an invisible threshold. Not because you've run out of options (you could generate a hundred more), but because you recognize that this is the one that matters. This moment is an experience of Threshold Intelligence. It’s a meta cognition of knowing when to stop. It's not a trendy buzzword or the latest productivity hack. It's a fundamental human capacity that's become critical in a world with very few, if any, limitations. Threshold Intelligence is our ability to recognize when enough is enough and when we should stop generating and start shipping. But what exactly makes up this capacity?
Threshold Intelligence consists of three interconnected capacities that work together to help us navigate abundance:
Perspective is our particular vantage point, shaped by our values, goals, and experiences. It determines which thresholds we consider significant.
Discernment is our ability to detect significant shifts in quality that go beyond measurable metrics. It's often more impressionistic than rational, more felt than calculated.
Taste is our inherited and trained sense of what is good or bad. It’s a muscle memory from past judgments. It’s our developed capacity for refined judgment. Despite its subjective elements, taste isn't purely arbitrary. It develops through experience, reflection, and exposure to quality work. The more we create, evaluate, and refine our choices in a particular domain, the more our taste evolves.
This kind of Threshold Intelligence allows—and prepares—us to recognize and experience qualities that transcend technical competence, a phenomenon best articulated by the architect Christopher Alexander. He called it "the Quality Without a Name" (QWAN)—an ineffable characteristic that some designs possess and others, despite technical adequacy, lack. Alexander observed that we can recognize this quality instantly, even when we cannot fully articulate why something works. It's the difference between a technically correct building and one that feels deeply alive. It’s the difference between a functional chair and one that invites sitting. This quality emerges from wholeness, when all parts work in harmony toward a unified purpose. It cannot be achieved through isolated improvements to components but requires a sensitivity to the entire system and its purpose. This is where judgment happens. What's most relevant to our discussion is Alexander's observation that this quality emerges most reliably from constrained systems.
The most enduring designs don't emerge from unlimited freedom but from engagement with limitations. At the center of the age of AI abundance is the paradox that without self-imposed constraints, we cannot achieve the wholeness that makes work truly satisfying.
Threshold Intelligence helps us recognize when those constraints should be applied, even when external limitations have disappeared. What we’re talking about is essentially rational vs. non-rational modes of judgment. Analytical versus instinctive or intuitive. True judgment requires both analytical and intuitive capacities. Either alone is insufficient. Purely analytical decision-making fails in the face of abundance because the variables become too numerous, the interactions too complex, and the weightings too subjective. We can't spreadsheet our way to wisdom when facing hundreds of high-quality options. Yet purely intuitive approaches can be inconsistent and vulnerable to bias and blindness. They may work for some but offer little structure for developing judgment in others.
The most effective judgment integrates both modes: using structured frameworks to focus attention, then allowing intuitive recognition to identify meaningful thresholds. The rational creates the conditions. The non-rational recognizes the moment. This integrated approach allows us to utilize the best of both modes: the clarity of rational frameworks, and the pattern recognition of intuitive sensing.
I’m eight hours into my day again. My screen still displays multiple windows of AI outputs, but something's different.
The positioning strategy for my SaaS client is selected and implemented.
The product imagery is finalized.
The B-roll sequence is chosen.
I close my laptop. This was a good day.
The options were as plentiful as before, but paralysis never set in. What changed wasn't the technology but my relationship with judgment itself. This morning, before opening a single AI tool, I exercised judgment deliberately. I judged what this client truly needed. I judged how much time this decision deserved: one hour to generate options, thirty minutes to evaluate and choose. I judged which criteria mattered most: alignment with the client's values, clarity for their specific audience, and distinctiveness in their crowded market. When the variations started flowing, I didn't see a stream of equal choices deserving endless consideration. I saw options that either measured up to my standards or didn't. I judged them, unapologetically and decisively.
I've found that three iterations is often the sweet spot for producing and judging work of any quality.
The first version explores the territory and sets the boundaries. You’re entering a divergent phase of work but without any limits whatsoever, you’re trapped in a loop of endless AI iterations that never come to a completion. Before you begin generating options, establish clear boundaries around time, iterations, and entities. Decide in advance that you will spend, say, 15 minutes generating options, then you will choose. For entities, you will only look at, for example, 4 different things (like, a person or group, an event, an idea, future hopes, past delusions, and so on).
The second refines the approach with criteria and analytical thinking. Defining what the finished work looks like is where you start but often not where you end up. Still, you want to converge what you’ve explored and judge what you have, which includes cutting, removing, adding, and changing. You’re deliberately limiting your options in an environment designed to provide unlimited ones.
The third polishes the work by paying close attention to your instincts and intuition, and asking yourself reflective questions. Our judgment is shaped by our embodied experience in the world—by how things feel, not just how they analyze. Did I recognize what’s meaningful in this situation? What am I sensing and feeling when I look at it—open awareness or contraction? Did I distinguish between variations and transformations? What could this mean to a stranger? What would I do differently in my decision process next time? Focus on practicing the capacity that AI lacks: the ability to recognize and make meaning based on embodied experience, contextual awareness, and values. This embodied quality of human judgment allows us to recognize thresholds that no algorithm can detect because they're felt, not calculated.
AI cannot tell us when something is good enough to stop iterating on because it cannot experience meaning. In a world engineered to keep us perpetually considering, the most revolutionary act is to judge. Call out what’s good. Call out what’s bad. Look, point your finger, and judge.
Talk again soon,
Samuel Woods
The Bionic Writer