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From Issue #44 June 5, 2014

Off the Grid

Making good crossword puzzles is even harder than solving them.

By Jon Seff Twitter icon

I trace my affinity for crossword puzzles back to my maternal grandmother. Sadelle used to (stubbornly) solve them in pen, and by the time she was finished correcting mistakes, the grid was a mess of ink that would make any self-respecting cephalopod squirt in solidarity. I liked the cleaner look — and erasability — of pencil, although family members would complain that the delicate No. 2 was too difficult for their aging eyes to make out.

What solidified my love for solving crosswords was Mrs. Latasa, my high school English teacher. She offered extra credit to anyone who’d drag themselves to school on Monday with a completed Sunday New York Times puzzle in tow. (Collaboration was encouraged.)

And then, about seven years ago, my fascination with how puzzles are made peaked: I wanted to make and publish a crossword puzzle. I had no idea where to start.

There’s a lot of software out there to help you create (or, more precisely, set) a puzzle. But as a longtime Mac user — and an editor at Macworld at the time — I was somewhat horrified to discover that the software everyone uses to construct puzzles is a Windows app called Crossword Compiler. I swallowed my pride and purchased a copy, installing it on my MacBook Pro running a virtualized copy of Windows XP.

Filling in the blanks

The first published crossword puzzle appeared December 21, 1913 (a Sunday) in the New York World newspaper. Its author, Arthur Wynne, was a journalist from Liverpool. His initial “word-cross” was a diamond shape with a hole in the middle, and devoid of the now-familiar black spaces.

By the 1920s, crosswords were a staple of most newspapers. Interestingly, the New York Times waited until the Sunday after Valentine’s Day in 1942 before running its first weekly puzzle — previously deriding them as “a primitive form of mental exercise” — and it took another eight years for puzzles to appear daily in the Times. The original impetus? Apparently to give readers something to do during the nighttime blackouts imposed on the coasts after the bombing of Pearl Harbor.

Puzzles today generally fall into three categories: standard, cryptic, and freeform. Standard (or American-style) crossword puzzles are what you’ll find in most US newspapers, and they feature diagonally symmetrical square grids and require that entries be at least three letters long. That’s the kind I’m most familiar with.

Cryptic puzzles, popular in Europe and other parts of the world, are often called British-style. In a cryptic, each clue is its own puzzle, usually comprising separate definition and wordplay portions; the break between the two can be tricky to discern. Freeform puzzles are asymmetrical, and are the easiest to construct because of their loosely interlocking grid structures.

A 14-letter word for a puzzle maker

For a cruciverbalist, the key to any good puzzle is the theme. Without a cohesive set of long answers tied together with a fresh and engaging theme, a puzzle is likely to be rejected by an editor. Whether it’s words that start or end with the same series of letters or sounds, famous women of song, or (especially with larger, Sunday-length puzzles) a riddle and answer, the theme is what makes or breaks a good puzzle.

“There are three components to a crossword: if it has a theme, all the entries have something in common; the fill holds it all together; and the clues guide the solver to that finished grid,” says Brendan Emmett Quigley, a professional (and prolific) puzzle maker who has created thousands of crosswords for the New York Times, the Los Angeles Times, USA Today, the Wall Street Journal, the Washington Post, and others. “And that’s the order in which an editor critiques the work. The easiest part to change is the last thing an editor looks at [the clues]. The hardest thing to change is the first [the theme]. If the theme isn’t developed very well, and you still make a grid and you clue it, all the rest of it is meaningless.”

Early on, I started a text file with theme ideas, to which I added whenever inspiration struck. My first accepted puzzle, published in the Los Angeles Times in 2007, had a pretty basic theme — all four-word constructions with words ending in ark — with only three long answers: walk in the park, shot in the dark, and way off the mark. That it ran as a Monday puzzle (in places like the New York Times and Los Angeles Times, puzzles get harder as the week progresses) was no surprise, but I was happy to finally have a theme that passed muster.

Once you’ve come up with a theme and your themed answers, and placed them in your grid, the setter’s challenge is filling in the rest of the grid. In the old days, when everything was done by hand, it was tedious — especially if you discovered that the grid wouldn’t work and you had to redraw a new one by hand.

These days, most pros rely on Crossword Compiler, a product from Antony Lewis’s WordWeb Software, based in Brighton, UK. It provides (or lets you create) grids, finds words to complete your fill, helps you with cluing, and exports formats accepted by most editors. The software reduces the tedium of the construction process and leaves more time and energy for thinking about making a solid, brainteasing puzzle.1

Launched in 1993, Lewis’s software was in direct response to a need in the market. “I tried making some puzzles, and found the software available at the time wasn’t much good,” Lewis says. “So I decided to write something better.”

Why has Crossword Compiler become the de facto app for constructors? “I guess it became dominant because it was better and more complete than anything else available,” says Lewis, who estimates that his users are pretty evenly split between pros and educators. “And I took and implemented a large number of suggestions from constructors, so it does what people actually want.”

Even with the software, I found the process of filling in a grid with words I felt comfortable using — not too obscure, not repetitive, and so on — to be a lot of work. A problem corner could take me quite a while to rework. Yet the thought of flying without a software net was something I could hardly fathom.

Quigley sees Crossword Compiler and computers in general this way: “Software makes life a hell of a lot easier. Before, you weren’t putting in anything that you couldn’t defend, because you were relying on things that you knew at your disposal. With a computer, you can pull up vast information in seconds with so many searchable databases where you can find words that would fit patterns (in addition to our own word lists). It’s very easy to pull up something that works. The question now becomes, Is this bullshit or are these legitimate answers?”

If you solve crossword puzzles regularly, you get used to seeing certain words, such as épée and aerie, that work well because of their strong vowel-to-consonant ratio, which makes crossing words easier to place.

The final piece is cluing, which can take a long time and feel like more of a chore than any other part of the process. In constructing puzzles, I definitely find writing clues to be the most irksome part — the step almost feels like needless busywork, a slap in the face after putting in the hard work of coming up with a strong theme and thematic answers, placing them in a grid, and filling the rest of the grid with the proper words.

But how you clue a puzzle can be a big part of what makes it fun to solve. It also contributes greatly to whether it’s easy or hard. Often, the difference between a Monday puzzle and a Thursday puzzle is how tricky the clues are. And clues are also where an editor has the most influence.

An example of a great clue: HIJKLMNO?. The answer, water. The clue is the letters H to O, as in H2O — the two hydrogen atoms and one oxygen atom that make up a water molecule. Simple when you see it, but potentially head-scratching otherwise.

“The most important thing with a puzzle is that is has to be solved. A puzzle maker has to expect to lose,” says Quigley. “No one should solve a puzzle and say, ‘I suck, this is too hard for me. Goddamn you, Brendan Quigley.’ That’s a failure.”

“It might not be easy,” he says, “but we do want you to solve it.”

Making it fit

For those curious about making puzzles, Kevin McCann’s Cruciverb.com — and its corresponding mailing list — is an excellent resource. It offers specifications and contacts for different publishers, pay rates, links to software, and more. Those who pay $35 a year (or $100 for three years) also get access to a treasure trove of information in the form of answer, clue, and grid searching databases, as well as historical data on published puzzles and downloadable word lists.

“When I first started the site [in 1996],” McCann says, “it was just a means for me to get my own crossword puzzles out there on the Internet, and hopefully get some feedback from solvers. Eventually I knew enough about how to make a publishable puzzle, and I figured that this type of knowledge-sharing really needed to happen on a larger scale. Surely there were other rookie crossword makers who could use the sage advice of those with experience. It was just a matter of time before expert constructors found my site and were quite happy to be part of this new online community.”

Cruciverb.com’s word lists — one with words from every puzzle in the database, and another specifically for words successfully used in New York Times puzzles — can be used with Crossword Compiler or other software to speed up and improve the construction process. I ponied up and found the databases and word lists invaluable.

Although McCann had several puzzles published in the New York Times, he decided early on that he would be better as a community builder and resource creator than as a constructor. “I have happily left that up to people who are much smarter and more imaginative than I am,” says McCann.

In addition to word lists and the like, Cruciverb.com is also a place for advice and mentoring.

Nancy Salomon got started making puzzles in the early 1990s. A disability forced her out of work, and she found that crossword construction was “something I could do on my own time schedule when I was able.” She took a beginners course and launched into writing large puzzles, which is an unusual way to start.

“That’s exactly what I advise my students against,” Salomon says. “I sold 21x21 puzzles to anyone who bought them: Newsday Syndicate, the Washington Post, the Wall Street Journal, Games magazine, the New York Times, the Los Angeles Times, you name it.” After that she got into the more common, daily sized 15x15 puzzles, often working with a partner.

These days Salomon isn’t doing much construction, but she has continued to generously mentor newcomers who are looking to break into the puzzle game. She’s helped probably 100 people over the years — including me — by giving feedback on themes and theme answers before people put in the extra work of filling and cluing the grid.

“Crossword construction has been a huge and rewarding part of my life,” adds Salomon. “The crossword community is open, accepting, and very generous with its time.” Of that, she’s a prime example. Salomon helped me improve some themes and answers that I’m sure made a big difference in their being accepted for publication.

Quigley’s foray into crosswords also came during some downtime. “I’ve always been interested in puzzles. Like anyone who’s interested in any particular field, they ask themselves, ‘Well, I wonder if I could do this,’” he says.

“In college I had a job where I photocopied documents at a law firm during the summer, and to pass the time I started doing the New York Times crossword. I wasn’t really any good at it, but I got addicted to it, and that semester I decided to try my hand at making them. A book had come out that had been out of print and they had just reissued it, called The PuzzleMaker’s Handbook, and it described how to make crosswords. I spent the rest of the semester trying to make one puzzle, and by stupid luck sold that one to the New York Times.

“The next three were rejected,” he quickly adds. “You learn more from rejections than you do from acceptances.”

I can attest to that last point. I had several puzzles rejected before selling one, and the feedback I got from my editor was helpful in crafting future puzzles to finally achieve a win.

Solving the grid

With the help of people such as Salomon, and a lot of trial and error, I eventually had a total of three puzzles published in the Los Angeles Times. The last two (aided by the skill of crossword editor Rich Norris) ran proudly on Thursdays. Those had more sophisticated themes — one used the clue Mark four different times, the other employed homonyms (Doe, Do, Dough, and D’oh) — and more themed answers.

For each I believe I was paid $75. (That rate is now $85; the New York Times pays $300 for daily puzzles.) If I add up all the time I spent constructing and all the money I dropped on software, it wasn’t lucrative by any stretch of the imagination. But it felt great to know that people all over the world were solving puzzles that I came up with, and even to find my puzzles deconstructed on a blog dedicated to the Los Angeles Times puzzle. And that feeling is a nine-letter word for immeasurable in value or worth.2

Jon has made one of his previously unpublished puzzles available for readers to download in PDF and standard .puz formats.

Photo by Giuseppe Milo.


  1. The Windows-only software starts at $49 for the base product, and it has piecemeal upgrades for the WordWeb Pro dictionary/thesaurus, additional word lists, and Pro Grid Filler to speed up the process of putting the rest of the puzzle together. An $89 bundle includes everything but Pro Grid Filler, while $169 gets you everything — I went whole hog. 

  2. Priceless. 

Jonathan Seff is an avid crossword solver, father of twins, and veteran technology journalist currently looking for his Next Big Thing.

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