Useful Constraints Turn Overwhelming Choice Into Focused Action

David Epstein’s central claim is not that freedom is bad. It is that people reliably overvalue freedom and choice in the abstract, then become overwhelmed by the amount of choice they actually receive. Too much freedom can make decisions harder, creative work flatter, attention more fragmented and commitment less likely.

The most useful constraint, in Epstein’s account, does three things. It blocks the lazy default. It clarifies what matters. It still leaves enough room to be surprised. If it leaves every option alive, it is too loose. If it specifies the answer so tightly that no discovery remains possible, it is too tight.

Epstein gives an evolutionary explanation for why this is hard to accept. Humans evolved under scarcity, not abundance. Too little food, too few routes and too few options were adaptive problems; too much choice was not. He compares the mismatch to sugar: humans evolved to want it because it was rare and useful, then entered an environment where it became abundant. Choice creates a similar appetite problem. People keep asking for more of it even when more makes them less satisfied.

That mismatch appears in people’s beliefs about creativity. In Epstein’s account of an international survey of known creativity myths, one of the most widely endorsed myths was that people are most creative when they are most free. He says it was tied with another myth: that group brainstorming is a good way to generate many novel ideas. People’s intuitions about the conditions for creativity often run opposite to the research he describes.

The same pattern appears in consumer life. Epstein says consumer options have increased by roughly a hundred-million-fold compared with pre-industrial societies, far outpacing the increase in wealth, which he puts at roughly 400-fold. Economic theory often models people as if more choice makes them better off. Human psychology does not behave that cleanly.

His entertainment example is infinite scrolling. Since its introduction, he says, people have become progressively more bored. In experiments he describes, researchers assigned some people to choose among 20 videos and others to watch one video drawn from that same set. The people assigned a single video were less bored than those given the menu of 20. Epstein’s interpretation is that human beings are “comparison engines”: the mere awareness that something else could be chosen weakens the experience of what is in front of us.

Barry Schwartz’s work on choice enters through the maximization scale. Epstein describes one end as “satisficing,” Herbert Simon’s term combining satisfy and suffice: define what good enough looks like, take the option when it meets that bar, and move on. The other end is maximizing, or what many now call optimizing: searching the whole option set for the best possible choice.

In Epstein’s summary, there is not much evidence that maximizers make better decisions, even though they spend more time making them. They are less happy with their choices, more prone to regret, less happy with their lives and more likely to prefer reversible decisions. Reversibility can itself become a trap because it prevents commitment. If the cost of agonizing were counted honestly, Epstein argues, satisficing would often be the long-run maximizing strategy.

Chris Williamson supplies the everyday version: a jeans store with one pair versus 20 pairs. In advance, most people say they want more options because more options seem to increase the odds of a perfect match. But after the decision, more options can bring paralysis, returns and second-guessing. Williamson suggests that if jeans could not be exchanged, people might be happier with what they bought. Epstein says similar studies have been run with other objects: people allowed to exchange an item are less happy with it than people forced to keep it.

Epstein connects this to Ellen Langer’s line: “Don’t make the right decision, make the decision and then make it right.” The claim is not that all options are equal. It is that people often imagine they can eliminate regret by perfect selection, when in many domains satisfaction depends on commitment after selection.

The preference reversal becomes sharper in serious decisions. Asked hypothetically whether they would want to be involved in choosing their cancer treatment, about two-thirds of people say yes, Epstein says. Among people who actually get cancer, he puts the figure closer to 10 percent. Agency feels empowering in the abstract. In the concrete, it can become a burden people want lifted.

Retirement plans show the same pattern through complexity. In Epstein’s description, when 401(k) choice sets become increasingly complex, people are more likely to make no decision at all, even when indecision means giving up free money from an employer match. He identifies anticipated regret as one mechanism: the fear of choosing wrongly becomes so aversive that no decision feels safer than a wrong one.

Williamson asks whether keeping options open can become “a form of self-harm.” David Epstein answers with a qualified yes: often, especially when optionality becomes an end in itself.

Useful optionality is not the problem. Early in a career, preserving options can make sense. But if every decision is evaluated mainly by whether it preserves more options, the harder question never gets faced: what is this option for?

Epstein uses Scott Stanley’s relationship research to describe “sliding versus deciding.” Younger people, he says, increasingly keep seeing where a relationship goes in order to preserve options. But if they remain in the relationship, options close anyway. They sleepwalk into escalating commitments: a drawer, a lease ending, moving in because it is convenient, perhaps marriage. Couples who slide into marriage this way are more likely to divorce and less likely to be happy than those who explicitly decide whether they are in or out.

Williamson extends the pattern beyond relationships. People can “fall backward through your entire life” in work as well as romance: a graduate job begins because someone at a career fair seemed nice, and a path hardens not because it was chosen but because it was convenient.

Epstein’s correction is not to reject exploration. Dating and careers both require taking data. The distinction is whether exploration is intentional. What am I doing here? What did I learn about myself? How does that inform the next pivot? That is different from merely “seeing what comes around.”

Herbert Simon becomes Epstein’s model for deliberate constraint. Williamson notes that Simon wore the same socks, ate the same breakfast, lived in the same house for 46 years and won the Nobel Prize. Epstein adds that Simon also won the Turing Award and the highest award in psychology. Simon coined “satisficing” because he thought humans were not equipped to behave like the optimizing agents of economic models. They cannot evaluate infinite options, predict all consequences or reduce life to utility maximization.

Simon’s narrow routines were not evidence of small ambition. Epstein says Simon believed people should proactively satisfice in areas where they can. One beret, one pair of socks, three sets of clothing — one worn, one ready, one in the wash — preserved cognitive bandwidth for the work he found meaningful.

The “Green Eggs and Ham effect,” as Epstein describes it, is a finding in psychology: people become more creative when the easiest solution is taken away. The name comes from Dr. Seuss’s Green Eggs and Ham, written after a bet that Theodore Geisel could not write a children’s book using only 50 words. The restriction blocked the obvious route.

With vocabulary unavailable as a tool, Seuss had to experiment with rhythm. Epstein connects this to a broader claim from cognitive science. Daniel Willingham’s line, as Epstein quotes it, is that “you may think your brain is made for thinking, but it’s actually made for preventing you from having to think whenever possible,” because thinking is energetically costly. Left alone, the brain reaches for the familiar phrase, the convenient solution, what neuroscientists call the path of least resistance.

That is why constraint can produce originality rather than mere inconvenience. Before Green Eggs and Ham, Seuss had been asked by a publisher to write from a children’s vocabulary list of about 200 words. The goal was practical: give children material they could read, but make it interesting enough that they would want to read. The publisher, Epstein says, saw children’s literature of the time as boring and treated the project as “an assault on illiteracy.”

Seuss looked at the list, found almost no adjectives, complained that it was “like trying to make a strudel without any strudels,” and decided to take the first two rhyming words on the list: “cat” and “hat.” That became The Cat in the Hat. The famous Seussian rhythm was not a free-floating inspiration. It emerged because the ordinary options were unavailable.

The same logic became institutional. Seuss co-founded a children’s book imprint that imposed vocabulary constraints, required pictures to run continuously across two pages, and required illustrations not to depict anything not described in the text. Authors who disliked the constraints were told they were not the imprint’s authors. Epstein’s reading is that the imprint became historically successful because it restricted the easy moves and forced willing writers into work they would not otherwise have envisioned.

Williamson presses the obvious tension: fewer words sound like more effort, not more freedom. Epstein agrees. Constraint is effortful because it prevents familiar phrasing. Without it, Seuss would likely have written closer to the literal children’s books of the time — “Johnny ties his shoes, walks to school” — rather than the “LSD absurdism,” as Williamson puts it, that made the work distinctive.

Williamson asks why fewer options can feel harder when decision-making is already such a burden. David Epstein distinguishes consumer decisions from creative decisions. In consumer contexts, more options typically mean more time spent deciding and more regret. In creative contexts, fewer options can feel harder because they force deeper thought within a limited space. Psychologists call this “desirable difficulty.”

The creative effect is not merely that there are fewer things to consider. It is that the remaining space gets explored more vigorously. Williamson gives the example of Jack Butcher’s Visualize Value: one font, one colorway, one design style, geometric shapes. That removed most of what a graphic designer might normally manipulate — typography range, color gradients, shadows, rendering. It concentrated the work on two questions: what idea is worth representing, and how should it be represented?

Epstein connects this to a constraints-led approach in sport learning. In that approach, the coach acts less as an instructor of repetitive motion and more as an architect of environments. Instead of telling an athlete exactly how to move, the coach sets restrictions that force the athlete to find their own solution. The approach has been around for decades and is having a moment, Epstein says, because Victor Wembanyama and Shohei Ohtani have publicly associated with it.

Kyrie Irving becomes a natural example. Epstein says Irving grew up with a backboard missing a chunk, forcing unusual angles, spins and finishes. In small-sided soccer, placing four-on-four play in a small space reduces the available options, but players explore those options more intensely. The constraint does not dictate the solution. It changes the environment so new solutions become necessary.

Creativity researcher Patricia Stokes gives Epstein the more general pattern: “paired constraints.” The first is a preclude constraint: identify and block the familiar move. The second is a promote constraint: require the use of something else in its place.

Claude Monet is Epstein’s canonical example. Painters were using light and dark shades to portray light. Monet blocked that route: no black. He then promoted pure color, placing colors next to one another like a mosaic to create the impression of light. Epstein says that was the birth of Impressionism. Monet banished black so thoroughly that, at his funeral, when someone draped a black shroud over his coffin, a friend objected — “no black for Monet!” — and replaced it with a floral tablecloth.

Constraints can also make work worse. Epstein says innovators often apply constraints repeatedly, and many attempts fail. People who produce successful innovations tend to have more failures. Edison had more than a thousand patents, most of which did not matter, and a few that changed the world. Copying what everyone else is doing competently may land a person near the middle. Trying to get somewhere new requires a structure that forces departure from the middle, but it does not guarantee success.

The boundary between useful and excessive constraint is one of Epstein’s clearest tests. In problem-solving studies he describes, people given 100 pieces and told to make anything are less creative than those given 20 pieces and told to make a piece of furniture. But if they are given 20 pieces and told they must make a chair, creativity drops. Too much freedom produces aimlessness. Too much constraint removes surprise.

David Epstein calls General Magic “the most important company nobody’s ever heard of.” Its importance, in his telling, lies less in what it shipped than in what its alumni learned after it collapsed.

General Magic was founded in the early 1990s by three former Apple employees, two of whom had designed the original Mac. The third, Marc Porat, had been responsible inside Apple for thinking about the next frontier after personal computing. Epstein describes Porat as a rare visionary. In a 1976 Stanford dissertation, Porat coined “information economy” on the first page and anticipated not only technological promise but dangers from automation and misinformation. In 1989, in a red leather notebook, Porat drew a thin glass rectangle with no protruding buttons: a touchscreen device with rectangular apps that would be a phone, computer, fax machine, ATM, video-game device, messaging device and more.

The web did not yet exist. Epstein says only 15 percent of American households had computers. But General Magic attracted money, talent and a 17-member alliance of international telecom companies so large that meetings had to begin with an antitrust lawyer listing what could not be discussed. Goldman Sachs took the company public in what Epstein calls the first “concept IPO” in Silicon Valley history: public with an idea, not a product.

The failure was not a lack of imagination. It was the absence of deciding constraints. The company defined its customer as “Joe Sixpack,” which Epstein says was “as good as no definition at all because nobody has met that guy.” Any promising idea went in. The team developed precursors to USB, emojis and other technologies. But the product kept expanding until it collapsed under its own weight. Epstein interviewed dozens of former employees, and roughly three-quarters said some version of: “I just couldn’t figure out what not to do.”

The emblematic story is engineer Steve Perlman’s calendar function. Perlman wrote it to run from 1904 to 2096, checked it in and thought it was done. A team leader said historical apps might require it to go back further. Perlman rewrote it from year one into the future. Then another team objected that year one reflected an arbitrary religious context and said the calendar should go back to the beginning of astronomical time. Perlman rewrote it to run from the Big Bang to the future. Epstein says the work took months; had they stayed with 1904 to 2096, it would have been four lines of code.

Porat had raised so much money, Epstein says, because he wanted to create “heaven for engineers,” where they were limited only by imagination. Epstein’s verdict is that what they needed was less freedom. The stock doubled on the first day after the company went public and was worthless two years later.

But the scar tissue became productive elsewhere. General Magic alumni went on to co-found LinkedIn, eBay and Nest; create Android, iPod, iPhone, Google Maps, Safari and other products. Tony Fadell, whose first job out of college was at General Magic, became one of the most affected by its collapse. He later led iPod design and co-founded Nest.

At Nest, Fadell made constraints literal: the team had to prototype the packaging before the product. If an intended feature or message could not fit into what the end user would see on a shelf, it was not a priority and went to the back burner. That, for Epstein, is what useful constraints often do: force priority clarification that talent and money can otherwise postpone.

For David Epstein, constraints are not only creative devices. They are also epistemic devices: ways to make learning possible. His example is the replication crisis in science, which he describes bluntly as the fact that much published research is not true. His explanation is that researchers often had too few limits on how they inferred truth from data.

The right sequence is prediction first, data second. A scientist, business or individual should articulate what they think will happen, gather data and then compare reality against that prediction. What often happens instead is that people gather data and retrospectively search for interesting associations.

Williamson names HARKing: hypothesizing after the results are known. Epstein compares it to a sharpshooter firing randomly at a wall and then drawing a bullseye around a cluster afterward. A later observer might think the shooter was accurate. In fact, the target was chosen after the shot.

A sharp break appeared around the year 2000 in trials of medications and supplements intended to improve cardiovascular health. Before 2000, many large trials were positive. After 2000, many became negative. Epstein says the change was procedural: a funding agency began requiring researchers to record their predictions in advance. With that constraint in place, researchers could no longer sift freely through the data and present retrospective findings as if they were predictions.

The same logic has been applied to businesses. Epstein describes a study in which companies were randomized into different types of market-research training. Some were trained in the scientific method: formulate a hypothesis about product-market fit, specify what customers would value, test it and update. Most of those companies discovered that some part of their theory was wrong and pivoted. They were more likely to succeed and start making money than companies that did not make strong predictions, did not test them and therefore did not learn.

The practical lesson is simple but demanding. Make more predictions. If trying a new exercise routine, a work process, a product feature or a career move, state what you expect to happen before the feedback arrives. Then adjust beliefs slowly according to the result.

Epstein’s cautionary scientist is Brian Wansink, the nutrition researcher associated with the “bottomless soup bowl” study. In that study, some subjects unknowingly ate from bowls refilled by a tube under the table; they ate much more than people whose bowls did not refill, leading to the conclusion that visual cues matter for satiety. Epstein describes Wansink as a poster child for non-replication science, with much of his life’s work retracted.

Wansink’s downfall, Epstein says, followed a blog post titled “The Grad Student Who Never Says No,” in which Wansink praised a student for going back into datasets after original predictions failed and finding something “true.” Other scientists recognized this as a textbook recipe for false positives. Epstein says about 18 of Wansink’s famous papers were ultimately retracted.

The broader warning is not confined to academia. Data without prior prediction can feel like learning while functioning as pattern-hunting. A constraint — say what you expect before you look — turns experience into feedback.

When Williamson asks whether designing with constraints leads to better designs, David Epstein’s answer is qualified but affirmative: in many cases, yes. His main example is universal design, which came out of the disability rights movement in the 1960s. Designing for the most constrained users often reveals problems that affect everyone.

Curb cuts were originally made for wheelchairs and turned out to help many more people. Web pages structured for screen readers required clearer hierarchical menus, which improved mobile web design. In Epstein’s telling, the constrained user often exposes a more general user problem in an extreme form.

His most concrete design example is military body armor. Epstein says he gained about 12 pounds while researching a chapter in which he ran an Army obstacle course wearing body armor from Vietnam to the present. Over time, especially during Iraq, armor had become heavier as soldiers were protected against shrapnel from many directions. They were safer in one sense, but could not move well, creating other dangers.

When women were first allowed into the close combat force, the Army had to design armor specifically for them. It was smaller, lighter, more mobile, modular and included features like a notch for a hair bun. But the design solved broader mobility problems: soldiers could raise their heads while prone and shoulder rifles more easily. Women were only one to two percent of the close combat force, Epstein says, but many men wanted the improved armor too. The Army rebranded it as unisex.

The Air Force cockpit story makes the same point statistically. When jets proliferated, accidents increased. Cockpits had been designed around average pilot measurements. A young lieutenant studied body measurements and found there was no such thing as the average pilot: even across three measurements such as arm length, thigh circumference and height, only a small share of pilots were near the middle range on all three. Designing for the average pilot had designed for almost no one. Adjustable cockpits reduced accidents.

The design lesson ties back to General Magic. The “average user” can be as fictional as Joe Sixpack. Designing for a constrained or specific user can reveal reality more clearly than designing for an abstraction.

David Epstein is more severe on multitasking than he expected to be. Some forms are possible: walking and talking, breathing while doing something else, or pairing a cognitive task with an automatic one. But two cognitively engaged tasks cannot be done in parallel in the way people imagine. What appears to be multitasking is task switching.

Each switch requires dropping one set of rules and activating another. Epstein cites psychologist Gloria Mark’s metaphor: the brain is like a whiteboard. When switching tasks, you erase it, but residue remains and interferes with the next task. That residue builds during the day until sleep.

Mark’s workplace research is, Epstein says, “the scariest thing” that went into his book. Around 2000, she found people switching tasks about every three minutes on average. By 2012, the average was 75 seconds. By 2022, it was 45 seconds, where it stayed for several years. The more switches someone makes in a day, the lower their end-of-day productivity and the higher their end-of-day stress, with effects visible in measures such as heart-rate variability and immune function.

The most disturbing finding is that attention is trained by interruption. If a person is interrupted all day by notifications, messages or other people, then later removes the external distractions and tries to focus, they will self-interrupt with intrusive thoughts at roughly the cadence to which they have become accustomed. Epstein describes this as an internal distraction barometer.

His remedy is not heroic willpower but blocks. If a person must answer dozens of emails or chats a day, do it in one, three, five or seven blocks rather than entering and leaving the inbox constantly. Mark’s work, as Epstein presents it, supports blocking as a way to regain some capacity for attention.

Epstein adds his own practice: keep a pad nearby for intrusive thoughts and write them down — cognitive outsourcing. He also uses what he calls the Hemingway principle. Hemingway would stop work in the middle of a sentence so that the next day he knew exactly where to begin. Epstein ends each workday by defining the important thing he will start with the next morning. This guards against two failure modes: falling into feeds and mindless browsing, or letting the inbox trigger the “mere urgency effect,” in which urgent-feeling tasks displace more important work.

Williamson connects this to larger-scale “macro multitasking” and periodization. His fitness analogy is that a person will lose more fat in six months if focused solely on fat loss, and gain more muscle in six months if focused solely on muscle gain. Across a year, separating the goals can produce better results than trying to maximize both simultaneously. Epstein agrees: the work becomes better, easier and probably more enjoyable when conflicting goals are not pursued at the same time.

Chris Williamson raises a contemporary backlash against optimization culture: tracking, restriction, routines and the sense that life has become homework. He sees people pushing back against over-optimization because they feel overwhelmed by optionality, chaos and uncertainty. David Epstein, who describes himself as a self-improver with some maximizing tendencies, recognizes both sides.

He gives a running example. As a Division I 800-meter runner, the better he got, the less he used some metrics. Eventually he stopped needing a watch because he understood the effort by feel. That felt freeing. Metrics can train perception, but at some point they can become burdensome.

His personal filter is to ask: if there were one behavior I wanted more of right now, and I could pick only one, what would it be? That question turns optimization into constraint. It prevents the pileup of improvement mandates — write five pages, train in a specific way, follow a dozen rules — that turns self-improvement into another source of overwhelm.

Isabel Allende is Epstein’s favorite example of someone “locked in” by ritual. He shadowed her while writing the book. Allende did not begin publishing books until about 40. Since then, for 44 years, she has started a new book every January 8th if the previous one is done. Epstein says she has produced a bestseller about every 18 months on average and sold 80 million copies.

Her life is organized around ritual. Every January 8th, she clears a room; before she had resources, Epstein says, she did it in a closet. She creates a quiet space, designates times, lights a candle to begin the workday, blows it out at the end and closes the door so the story stays there. She places a book of Pablo Neruda poems under her computer. Epstein compares these cues to a basketball player’s free-throw routine: three dribbles and a clap are not magic, but they associate the body with a performance state.

Her family respects the seasonality. Epstein says they told him that if anyone wants something from Allende, they need it by January 7th, because after that her outward-facing life disappears.

Then Allende disrupted her own structure. Epstein reads an email she gave him permission to share. She had started a novel on January 8th and, for reasons she did not explain, set herself a deadline to finish a first manuscript by the end of March. Her agent and brother liked it. It needed polishing, but by May she found herself without work until the next January 8th. She wrote that she was “going crazy,” getting rid of clothes, replacing furniture, walking in circles, reading compulsively. Epstein’s book, she said, had been an inspiration because she needed “a task with boundaries.” At 84, with no obligation to keep writing, Allende wrote: “This freedom is lethal.”

Epstein’s own routines are less dramatic but follow the same principle. He works in blocks. At the end of each workday, he decides the important thing to begin the next morning so he does not wake into decision-making. He sets decision rules. His newsletter is a deliberate satisficing exercise: if a book must be a nine or ten, the newsletter can go out when it reaches, by his own subjective judgment, a six and a half. That rule matters because otherwise his maximizing tendencies would prevent him from shipping.

David Epstein revises a common reading of Robert Frost’s “The Road Not Taken.” The poem is often quoted as an ode to rugged individualism: take the less traveled road, and that will make the difference. Epstein says that is not what Frost intended.

Frost was, according to Epstein, teasing or criticizing his walking partner Edward Thomas, who would agonize when two roads looked the same. No matter which road they chose, Thomas would later say they should have taken the other one. Epstein points to the poem’s details: Frost says both roads were “just as fair” and that neither had footprints from that morning. The poem is not straightforwardly about choosing the path fewer people have trod. It is about the human urge to imagine the counterfactual and regret the unchosen path.

Chris Williamson connects this to Hamlet: “Thus conscience does make cowards of us all.” In his reading, Shakespeare is not attacking morality. “Conscience” there is closer to consciousness — the ability to think ahead, judge ourselves and simulate futures before they arrive. That ability is intelligent and ethical, but it can paralyze. Humans can experience imagined consequences emotionally in advance, making possible futures feel real enough to prevent action. “Courage isn’t defeated by fear,” Williamson says. “It’s defeated by simulation.”

Epstein agrees that counterfactual thinking is both blessing and curse. Human beings need imagination to plan, compare, create and improve, but the same capacity makes freedom psychologically expensive. We can picture every other option, regret every road and keep every door open until no choice is really chosen.