Creating Crossword Puzzles for Fun and Profit: A Visit with Christina Iverson

Christina Iverson with my grandson Wally.

The first time I noticed the name Will Shortz was when he was editor of Games Magazine from 1989-93. I remember the name because during that time I submitted a story to Games comprised of one-third homonyms titled How Eye One the Wore. (It was accepted and published!)

Years later I noticed that he'd become crossword puzzle editor for the New York Times. Simultaneously he's been Puzzle Master on NPRs Weekend edition and even wrote clues for The Riddler in the film Batman Forever. He's not only authored or edited 100 books himself, he's built up a collection of 20,000 puzzle books from as far back as 1545. It's no puzzle where his interests lie.

So it was exciting for me when I learned that my daughter had not only taken an interest in making crossword puzzles, she'd also had one of her puzzles accepted by the New York Times.

Through her I've since learned that there's a lot more to those New York Times crossword puzzles than I'd previously realized. Therefore, it seemed like a cool idea to pick her brain and share here what I've learned.

EN: When did you first take an interest in crossword puzzles?

Christina Iverson: Last summer, Joey (my husband) and I started doing the NYT early-week (easiest) puzzles. I had always thought of the crossword as too hard, and mostly about useless trivia. It turns out I was wrong! Solving crosswords is one of those things that just takes practice. Once you get a feel for how the clues work, and what the themes are like, it’s much, much easier. We started doing them because we had a 6-month-old son who was still waking up a lot in the evenings once we put him down for bed, and it was hard to find things to do together that could be easily interrupted. I also felt like after spending all day long as a stay at home mom with a baby, I wanted to do something to use my brain. Crosswords were a perfect solution.

Crossword puzzles are nothing new. This London Times
crossword puzzle was published in 1939.

EN: What prompted you to start making crossword puzzles yourself? That seems like a pretty big leap?

CI: I was really intrigued by the words that were used in the puzzles, and noticed a lot of words being used over and over again. It seemed like every other puzzle had the words “EPEE,” “ETON” and “APSE.” I was curious why certain words were used so much, and how computer-generated the process was. I read a couple articles in the NY Times about how puzzles were made, and I thought it would be fun to make a puzzle for Joey as a birthday or anniversary present. I imagined it would take me a year to make a puzzle, because it just seemed impossible to me. It ended up just taking me a couple of days to make the first puzzle, themed about our cat, George Melvin. I had so much fun making it, I announced to Joey I had a new “life goal” of getting published in the New York Times. At the time it seemed like a lofty goal, and he seemed a little surprised, so then I clarified, “Or, at least, making a puzzle good enough to try to submit….” But, after getting a puzzle accepted in just a few months, my new aim is to be able to make crosswords as a part time job.

EN: What are some features of the NY Times Crossword that average people are unaware of?

CI: The thing people seem least familiar with when I talk about making puzzles is the concept of a theme. Sunday through Thursday puzzles are themed puzzles, where (usually) the longest across entries are related to a theme, often based on wordplay. Monday puzzle themes are the most and straightforward, getting trickier as the week goes on. Sunday puzzles are not the hardest, but have a bigger grid, 21x21, compared to a weekday puzzle which is typically 15x15.

Some of my favorite themes use homonyms, spoonerisms or puns to make wacky phrases that are clued in funny ways. The best puzzles have some sort of “aha!” moment where the solver figures out what’s going on. Many puzzles have a “revealer” phrase that tells the solver what’s going on. For example, in an early-week puzzle like this one, the revealer is “PET SOUNDS” and each theme entry has an animal noise hidden in it, like “THIS SIDE UP” and “TWO OF A KIND” An example of a trickier late-week theme would be like this one, where the entire right half of the grid has the answers appearing backwards, and the center represents “THE LOOKING GLASS.”

EN: What is the process for creating crossword puzzles for publications like the NY Times?

CI: The first and most important step is creating the theme for the puzzle, and coming up with theme entries. The theme is what makes or breaks a puzzle, and you just can’t get anywhere without finding a solid and consistent theme with strong entries. This is what I struggle with most.

While some people work on grid paper, there is really great software that most people use (I use CrossFire). The theme entries are then placed in an empty grid, and black squares, or blocks, are put symmetrically around the grid. The goal here is to segment the grid in a way that’s possible to fill, but doesn’t have too many words, or especially too many short words. The software I use is really helpful in filling the grid with non-theme words, but it still takes a human touch to make a grid with strong “fill.”

The dictionary used in the software ranks words based on quality, and a grid can be “auto-filled” with what the computer decides works well. However, the software doesn’t really know what words and phrases are fun for solvers or clue-writers. For example, in a puzzle I just submitted, the auto-fill feature suggested the words “RASSLED” “MODERATO” and “ERITREAN,” whereas I put words in those slots that I think are more fun -- “BOSSMAN,” “LOVE LIFE” and “EVIL GRIN.” Other examples of boring or bad fill would be too many acronyms, foreign words, or obscure words. Filling the grid is my favorite part of making a puzzle.

The last step is writing the clues. I think most people think of the clues as being the most important part of the puzzle because it’s the part that the solver interacts with the most. However, I’ve heard about half of the clues have been changed by the editors, and editors wouldn’t accept or reject a puzzle based on the clues.

Go online and you will can find oodles of puzzles.

After mailing the puzzle in to the NY Times, it takes about 3-5 months to hear back from the editing team about the puzzle. The puzzle I submitted that was accepted came with a request for some minor revisions to the grid, so I did a little editing to change two sections. It will take many more months for the puzzle to actually be published. The NY Times pays $500 for a weekday puzzle for new puzzle creators, and more for those who have published 10 or more puzzles. There are also other publications that take submissions. Another puzzle I made that was rejected by the NY Times will be published by The Inkubator, which publishes only puzzles made by women.

EN: What is it that makes doing crossword puzzles so compelling for people who are into it?

CI: I can’t speak for other people, but for me, it’s been about doing something where I am using my brain, but in a fun and relaxing way as well. As a stay-at-home mom, I’d go crazy if I wasn’t doing something where I get to be creative and think about things other than babies. I am actually still not that great at solving puzzles, and use Wikipedia a lot when I get stuck. I really like when I figure out what’s going on in a tricky puzzle, though, it’s quite satisfying!

EN: Any advice for others who want to make puzzles themselves?

CI: YES. Find a mentor! There are a lot of constructors who like to mentor new constructors, especially women or underrepresented groups in the “crossworld.” I worked with Ross Trudeau when I first started out, and got advice from Amanda Chung. Then I reached out to Jeff Chen, who runs the very helpful website xwordinfo.com. We’ve worked together on a few collaborations, and he’s really challenged me to improve the quality of my puzzles.

I also think it’s worth investing in software and a membership to xwordinfo.com, which comes with the use of a word list. I would also recommend Patrick Berry’s Constructor’s Handbook. Just one published puzzle more than pays for these small upfront investments. If you want to construct good puzzles, you should also be doing puzzles every day, and reading comments about them. There are many blogs that blog every day about the NY Times crossword and other crosswords. Rex Parker is one particularly notorious blog that gives pretty harsh critiques. I’ve learned a lot by reading it, but am pretty nervous about how he’ll rip my upcoming puzzle to shreds!

* * * *

"The nice thing about doing a crossword puzzle is, you know there is a solution."
--Stephen Sondheim