The Prudence Trap

Box Checkers work extremely hard, but it is neither an usually high pain threshold nor a remarkable tolerance for sleep deprivation that sets them apart. It is speed and efficiency. They have a sixth sense for spotting the relevant boxes, checking them, and sprinting ahead before most of their peers even realize there are boxes to be checked.

Key to the success of Box Checkers—and why most appear if not wise beyond their years, then old souls in young bodies—is an almost alarming lack of sentimentality about their work. Box Checkers do not get lost in reverie. They are not tempted by self-enrichment or self-discovery. Their goal is personal advancement, and they obtain that goal by checking the right boxes as expediently as possible.

Such an approach can make Box Checkers seem a bit robotic, for neither passion nor pique tends to mar their efforts. It’s not that they seem dead behind the eyes. (Box Checkers are always smiling and high-spirited.) But they give the impression that they would be just as dedicated and vigorous in checking other boxes so long as they were the right boxes to be checked.

Notably, for those supervising them, it is precisely this bloodless quality that makes Box Checkers so easy to work with. Their efforts are never evidence of some deep vocational calling or the expression of a moral, spiritual, or creative commitment. They are simply what is required to check another box. Box Checkers therefore follow instructions with the discipline of a bomb squad; in a narrow sense, their work is perfect. The numbers always add up, the grammar is spotless, and whatever the endeavor lacks in genius, it is more than made up for in the lack of trouble it presents.

This is no small thing. Box Checkers keenly appreciate that the key to making the best impression is to be entirely inoffensive—not in terms of refraining from the use of four-letter words but in studiously avoiding any behavior that creates friction. Box Checkers know not to make demands, not to ask for consideration, and never ever to take a radical position.

Their goal is to make life easy for absolutely everyone around them.

This doesn’t mean that Box Checkers are kiss-ups. Kiss-ups draw attention to themselves. They put a little too much shine on the apple, making them seem untrustworthy. Instead, Box Checkers are keenly attentive to others and rigidly considerate. You might say they treat most everyone around them as if they were a familiar face at the Four Seasons and they were the head concierge.

And what about those they view as gatekeepers to their continued ascent? With such individuals, the conduct of Box Checkers is essentially the same, though they elevate their conscientiousness to an art form. They remember facts about you, write thank-you letters, and routinely check in. They know that you are a box to be checked—a critical one at that—but unlike other boxes, the checks we make to human ones have a tendency to fade and must constantly be rechecked.

Setting a trap for yourself

By and large, ambitious parents don’t thrill to the idea that their children are best advised to embrace the qualities of a Box Checker. And yet, it is important to emphasize what Box Checkers are not. They are not sociopaths, and nor are they arrogant snots. They are merely people who are supremely prudent in the pursuit of their own self-advancement.

Prudence is not a term you often hear nowadays. Whether as a personal virtue or a behavioral protocol, it seems out of step in a “move fast and break things” world. But prudence, supreme prudence, is the key to the Box Checker’s success.

How so? Let’s go back to my earlier remark about the all-American athlete. In 2024, there were exactly three high-school students in the United States who broke a 4-minute mile at a track and field event. Mind you, the first person to run a 4-minute mile was Roger Bannister in 1954, less than a century ago, when he was a 25-year-old medical student.

Breaking a 4-minute mile is an almost unbelievable feat under any terms, but especially for a teenager otherwise cramming for AP Bio. By contrast, the overwhelming majority of feats notched by overachievers between the ages of 15 and 25 are eminently believable. Straight As your junior year? Believable. Winner of an essay competition? Believable. Glowing reviews after your first year at McKinsey? Definitely believable.

Such achievements are impressive but unexceptional. Promising young people rack up accomplishments like them every day. Moreover, if you are just such an individual, impressive but hardly exceptional, your competition is not with the 4-minute milers of the world, because there simply aren’t enough of them to fill up the entire roster of elite opportunities. There are vanishingly few individuals under 25 who do something truly extraordinary, but there are tons of young people who do impressive things. And for those who are merely impressive, who cannot otherwise stand out by some singular accomplishment, the box-checking mentality is essential. You understand that your success hinges on two factors that are intertwined: brute efficiency and a capacity for never making a mistake.

“Take the instant way,” Ulysses urges a pouty Achilles in William Shakespeare’s Troilus and Cressida, when the prima donna of Greek warriors takes a break from the Trojan War:

For honour travels in a strait so narrow,
Where one but goes abreast: keep then the path;
For emulation hath a thousand sons
That one by one pursue: if you give way,
Or hedge aside from the direct forthright,
Like to an enter’d tide, they all rush by
And leave you hindmost

Set aside the irony that the demigod Achilles is actually the 4-minute miler of murdering Trojans (he is truly exceptional), in luring Achilles back to the battlefield, the wily Ulysses makes a point that Box Checkers everywhere have taken to heart. In a world where everyone is competing for the same honors, if you are merely impressive, forget taking a giant leap—you can’t afford to miss a step. Prudence, joined with unrelenting application, is the best chance you have for success.

But what does it mean to internalize this lesson as a lifelong strategy for personal advancement? In The Theory of Moral Sentiments, Adam Smith reflected on an unlikely hero, “the prudent man.” For Smith, this figure is the cornerstone of the kind of stable, thriving society he envisioned in his other great work, The Wealth of Nations. Nonetheless, the Glasgow University Chair of Moral Philosophy had deep misgivings about this peculiar character type.

The “first and the principal object of prudence,” Smith wrote, is “security,” and achieving that goal is a matter of patient industry as well as a peculiar mindset. We endeavor to achieve “real knowledge and skill in our trade or profession,” he said, and display “assiduity and industry in the exercise of it.” We work hard, develop our talents, and then consistently apply them in furtherance of our success. But if we are prudent, we don’t merely put our noses to the grindstone. Our efforts are tempered by two qualities: risk aversion and self-involvement.

“The methods of improving our fortune, which it [prudence] principally recommends to us, are those which expose [us] to no loss or hazard,” Smith contended. We not only stick to well-trodden paths of personal fortune; we are uninclined to heed the calls of sympathy, loyalty, or civic spirit. The prudent man “confines himself, as much as his duty will permit, to his own affairs,” Smith said. He can be counted on when he knows he must be counted on, but he won’t otherwise go out of his way if doing so would risk some disadvantage.

Prudence, as such, is a virtue whose principal aims are self-protection and personal advancement. It ensures that we pay our taxes in a timely fashion while also preventing us from ever running into a busy street to save a child. Morally speaking, the downsides of such a virtue appear obvious—prudence “commands a certain cold esteem,” Smith wrote, “but seems not entitled to any very ardent love or admiration.” But when practiced with the near-religious rigor of the Box Checker, it also creates a trap of sorts that limits the scope and substance of a lifetime of accomplishments.

Because the Box Checkers’ chief advantage is not excellence in some specific activity but superior competence in all matters, they spend all of their time thinking about two things: how to stay a step ahead of the competition and how to keep from tripping. It’s a dreary way of living your life, one that trains you to prize a fairly narrow set of achievements that catch the eye on a résumé over any accomplishments you truly care about.

And what happens to the Box Checker when it seems like there are no more boxes to be checked?

I recall a conversation with a friend from law school, a Box Checker’s Box Checker, who had a string of accomplishments that made him the envy of most everyone around him. He had graduated near the top of his class from an elite university, racked up two distinguished fellowships, and subsequently launched a national organization that put his name on the tip of everyone’s tongue. He succeeded in a similar fashion at law school, checking one box after another: a top slot on the law journal, platinum internships, a clerkship with a legendary appellate judge. And then, on the cusp of a signal triumph, the ultimate box of a legal education, his luck inexplicably ran out. He failed to secure a Supreme Court clerkship.

Shortly afterward, I gave him a ride home one night. My friend was pensive; he seemed lost. He told me that he had a position waiting for him on the East Coast at a hedge fund and another on the West Coast in a district attorney’s office. They were two phenomenal job offers by any reckoning, and still they seemed to make no impression on him. Finally, he turned to me. “John Paul, what is the next thing you should do . . .” he asked, his voice trailing off.

The thought was incomplete, but the dilemma was clear. What do you do when the boxes run out or, to be more precise, when there are none that are self-evident to everyone around whose opinion counts in matters of self-advancement? Rather than chasing dreams or committing himself to a cause he truly cared about, my friend had spent his whole life checking boxes. He had been so successful in that endeavor that now he seemed paralyzed, trapped. His education had taught him to keep his head down, to keep looking for boxes to be checked. And now that his education was done, now that he had failed to check the box that would put him once again beyond any doubts about his professional choices, relieving him, for at least another year, from actually having to think hard about them, it was as if he had lifted his head and looked around only to discover a world that was alien to him.

My friend turned out all right in the end, as all Box Checkers do. The supreme prudence that underwrites their adolescent and young adult endeavors ensures that they continue to rack up a streak of impressive accomplishments. They don’t change the world, no, but they pay their taxes, purchase second homes, and enjoy a steady stream of kudos on LinkedIn.

John Paul Rollert is adjunct associate professor of behavioral science at Chicago Booth.