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Last Friday morning — September 11, 2026 — tens of millions of Americans experienced a horror unique to our age. As they sipped their first cups of coffee and listened to public radio rehash the calamities of 25 years earlier, they turned to their phones in search of a distraction from the memories, or perhaps simply out of habit. They fired up the NYT Games app and began to play Spelling Bee. This is the game in which you are given seven letters, arranged in a hexagon, and must make as many words as possible out of them, always using the letter that occupies the hexagon’s center; the longer the word, the more points you score. If you use every letter in a single word — a pangram, they call it — you get bonus points. Get enough points, and the app dubs you a “Genius.” Last Friday’s letters were: i, h, c, d, a, e, and, at the center, k. So, naturally, we all entered dickhead — a 15-point pangram! — as our very first word, only to be denied.

“Not in word list,” Spelling Bee informed us.

To be fair, we — I — were not expecting Spelling Bee to approve of dickhead. “Our word list does not include words that are offensive, obscure, hyphenated or proper nouns,” says the NYT’s Glossary of Spelling Bee Terms. And dickhead certainly is hyphenated obscure! These days I mostly hear it used in British comedy shows, rather than on the mean streets of well-gentrified Brooklyn. Who even knows what it means?

More troubling, though, is that ackee is also not in word list. Ackee, as we all know, is the Caribbean fruit that is an inextricable component of ackee and saltfish, considered to be Jamaica’s national breakfast. It’s neither offensive nor hyphenated nor a proper name. Is it obscure? Perhaps, but no more so than prion or corolla, both of which are in word list. Still, it’s absences like this one that have, in the past, prompted me to swear off Spelling Bee, to pause my NYT Games subscription — or to delete the app from my phone entirely. There’s a deep frustration to being told that a word you know is a word is not a word.

Back in 2021, Slate asked Spelling Bee’s editor, Sam Ezersky, how he decides what’s in word list:

All of this is fair. His puzzle, his rules. Only a dickhead would get truly upset over a game.

Which is why, after complaining to my brother, Steve, who’s a Spelling Bee completist, I went on to work the puzzle, achieving Genius status not longer afterward, and without using any low-scoring four-letter words. As always, I was tempted to keep going, to attempt the secret-but-not-really level of “Queen Bee,” which signifies you’ve found every possible in-list word that can be made from the seven letters — that there’s nothing more to do. But I didn’t. After a certain point, I can’t be bothered to keep going, to complete just for the sake of completion. I’m a half-assed Sisyphus — as long as the peak of Mount Tartarus is in sight, I can call it a day and let that boulder roll.

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Which is honestly what has confused me for a long time. I love puzzles. Crosswords, especially — I solve the Times puzzles Thursday through Sunday, and I even used to edit Maura Jacobson’s weekly crosswords back at New York Magazine. I delve into Spelling Bee regularly, and Connections when I remember it exists. I’m also a math guy, and my social feeds lately have been peppered with images of intersecting circles and odd exponential equations. Part of the reason I like rock climbing is that it requires puzzle-solving as much as physical ability — you have to know how your body can move, how gravity works (or doesn’t), and specific sequences of small movements that unlock the mystery of what climbers call a boulder “problem.”

At the same time, actually finishing a puzzle often leaves me feeling empty. All the small triumphs along the way — an obscure politician’s name dredged up from memory, a pun resolved after a minute of pondering — should add up to one big climax: the satisfaction of a grid fulfilled! And that satisfaction should last. I should be able to sit with it, luxuriate in it like a hot tub, the effervescent heat pleasantly suffusing my body until, at last, I’ve had enough, clamber out, and enjoy the fresh chill against my skin.

Instead, success is muted by disappointment. If I’ve taken a while to finish, I’m frustrated — I’ve underperformed. And an average time is, well, average¹. But even when I’ve sped through a challenging puzzle, I’m annoyed — instead of spending time with each clue on its own, and enjoying the process, I’ve rushed, and now I’m done, and there won’t be a new puzzle till tomorrow, or even next week, unless I delve into the archive (which I’ve been doing; I’m back into 2019 now), and still I know that awaiting me there in the grids of the past is the same ambivalence. I’m an addict, chasing a high I’ve never fully experienced.

Completion isn’t the only reason we do puzzles, I know. They’re about the process, about twisting your brain in just the right way that a mystery resolves itself with crystalline clarity. We solve them as entertainment and as training, to keep ourselves amused and sharp in equal measure. They’re very much a “The journey is the destination” pursuit.

What I’m hungering for, puzzle-wise, is the inverse — a destination that is the destination! Part of the problem is structural: Most puzzles, though they may be numbered and ordered, exist asynchronously. That is, you can solve them in any order you like. If they have a central theme, you might figure out the associated clues early enough that what finishes the puzzle for you is a simpler clue — perhaps a three-letter word for the Kiwi greeting “kia ___!” And while that may fill the grid, it bears no relation to the central theme. It means nothing in the context of the puzzle as a whole. It does not fill my heart.

What I want in order to feel satisfied is meaning. I want each puzzle to amount to something, not just in the clues associated with its theme but across (and down) the board, with every clue leading toward an ultimate challenge, something that would build on everything I’d figured out up to that point and allow me to finish with a flourish. I want drama, I want catharsis — I want five acts, not one. I want to imagine Sisyphus _____.

This is very, very hard to do! Making a regular crossword puzzle is difficult enough, and contorting the format² or adding new layers is guaranteed to piss off regular solvers. At New York, Maura Jacobson once ran a puzzle whose top half had no numbers and whose bottom half had no black squares. Readers hated it! But it was one of her all-time best.

Inventing a whole new puzzle format is no easier. Twenty-two years ago, I worked with the puzzle maker Matt Gaffney on a new concept for New York. I think it somehow revolved around the news of the week, the boldfaced names covered in the magazine’s pages, but what I remember well — what guaranteed it would never run — is that it didn’t have a real payoff. When you were done, you were just … done, without even the satisfaction of a big completed grid. No payoff, no meaning, no puzzle. We understood. We let it go.

This is, incidentally, what I detest about Wordle. It’s all payoff, and not one iota of meaning. In Wordle, whose rules I hope I don’t need to explain to any of you who’ve read this far, you don’t need to understand anything. There are no clues. The solutions are context-free. All you need to know is every five-letter word in the English language, and the relative frequency of consonants and vowels. And all those words are effectively identical: aloha is slate is pudgy is guano. But what a payoff when you find the right word! You can give yourself credit for a good starting word, for your well-honed strategy, for simple dumb luck. You had one job — to figure out a single five-letter word — and you did it! Success! You can move on with your life, glowing with accomplishment, unchanged by your experience. You can call me a dickhead, but: Wordle is Sudoku for people who can’t math.

(Don’t get me started on NPR’s Weekend Edition puzzle.)

For my own personal cryptic challenge, there is, alas, no solution. Though it often seems like this Trying! newsletter wields enormous cultural power, I do not expect the world’s puzzle-makers to immediately bend to my needs. Still, I am putting this idea out there — the idea that a puzzle can amount to more than a solvable grid and a few mediocre puns, that it could and should have narrative and meaning — in the hope that it may sway, however slightly, the future of enigmatology. These setters are people of the word, after all, and they must realize that within their hands lies incredible power, not just to distract us from reality for half an hour at a stretch but to make sense of that reality in fresh, new ways. In a sentence or two, I will have finished this essay and scheduled it for delivery, and when I click “send” I will feel a sense of completion I never get from a crossword: This piece of writing may be at an end, but its life has just begun, and I get to observe it all — how it’s read, who reads it, whether it changes a damn thing or not. There’s a chance, too, that it, or one of the other essays here, may even outlive me, and go on carrying meaning through the universe for decades or centuries to come. What started with me might end in the stars. Or not! You got a seven-letter word for that? 🪨🪨🪨