“The Puzzler” Is a Wild Ride Through the World of Puzzledom

Ben Zimmer
Beyond Wordplay
Published in
9 min readJun 6, 2022

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Author A.J. Jacobs and puzzlemaker Greg Pliska reveal their puzzling secrets.

A new book from A.J. Jacobs is sure to pique the interest of Beyond Wordplay readers: The Puzzler: One Man’s Quest to Solve the Most Baffling Puzzles Ever, From Crosswords to Jigsaws to the Meaning of Life. In it, Jacobs explores just what makes puzzles so enticing. He enlisted the help of expert puzzlemaker Greg Pliska to concoct a suite of brand-new puzzles for the book, and Pliska also headed up a team that created a full-fledged puzzle hunt that accompanied the book’s publication. (On June 4th, the puzzle hunt was solved by Benji Nguyen and his teammates, who will split the grand prize of $10,000.)

We recently had a chance to sit down with Jacobs and Pliska to learn about how the book came together, and how the puzzles for the book and the hunt were designed.

BW: A.J., you’re known for books that involve “lifestyle experiments,” like The Year of Living Biblically and The Know-It-All. So how did you get inspired to make your latest “lifestyle experiment” all about puzzles and puzzling?

AJJ: It was actually one of the stranger origin stories, because I had a contract to write a totally different book. It was all about the post-truth crisis and trying to fact-check everything in my life. Like, how do I know the world is round? How do I know my wife really loves me? And actually, I do still think it’s an interesting idea, but I was miserable. It’s such a morass and I was worried I would do more damage to the discourse then help it. And so my agent, three months in, just said, “Well, why don’t you try a different book on something you really love?”

And he knew I loved puzzles, especially crosswords. So he said, “Why don’t you see if you can make that?” And I went to the publisher, and she was very nice and said, “Okay, we’ll try it.” And thank God it worked out. The research was just a delight, and getting to embed myself in the community and to work with Greg Pliska. You know, it doesn’t get better.

BW: So what was your first route in? You started with crosswords?

AJJ: I’ve always been a word nerd. And five years ago, I had the pleasure of being 1-Down in the New York Times crossword puzzle: “A.J. ___, author of The Know-It-All.” And of course, I thought this is the highlight of my life, you know, better than my wedding. And then my brother-in-law, he did congratulate me, but he also pointed out, correctly, that it was the Saturday New York Times crossword puzzle. And as you know, all of the answers on Saturday are either incredibly hard wordplay or totally obscure. So his point was, this is not a compliment, this is proof that you are totally obscure.

And then I told that story on a podcast and it happened that Peter Gordon, a great constructor, was walking his dog, heard the story and decided to rescue me and put me in the Tuesday puzzle. And not just as a clue, he made the theme of the puzzle a quote that I had said, about how I’m going to be a loser until I make it into a Tuesday puzzle. And so he turned that into a quote as the theme.

I remember I was doing that puzzle, because I do it at 10 o’clock at night, as soon as it comes online. I remember I was sitting next to my son and I was doing the puzzle, and I said to my son, “Something very weird is happening.” I thought that someone had hacked into my computer and made a fake puzzle as a joke. And then I got an email from someone, “Did you see the puzzle today?” And I was so freaked out. It took me like an hour and a half to do the puzzle, because I couldn’t even remember what I said, so I didn’t even remember the quote.

That’s the whole story, and I thought this is a great way to start the book. And then I can open it up into all kinds of puzzles, and feature original puzzles.

BW: The coverage of puzzle types is very comprehensive. You cover everything from physical and visual puzzles to word puzzles. Did you find yourself equally gravitating toward all the different types of challenges, or were some more of a chore?

AJJ: Word puzzles are sort of my go-to, that’s what I truly love. But I wanted to explore other types of puzzles, especially because as a kid, I was really into mazes. I would draw pencil mazes, and I would love the visual puzzles. So I knew I wanted to cover every different type of puzzle. A lot of those puzzles did not come naturally to me at all. I have terrible spatial reasoning, so, you know, it took me 52 years to do the Rubik’s Cube. I only did it because I did this book, and it took me eight times as long as my son. I’m okay at math, but it’s not in my DNA as much. So they were more challenging, but I wouldn’t say I was bored at all.

I think that it was fascinating to try these new ways to stretch my brain. And so in some ways it was, it was kind of the more exciting part of the research to do these puzzles that I had no idea about. I didn’t know Japanese puzzle boxes existed three or four years ago. And it’s this enormous cult where people pay thousands of dollars. I love that. I think I would not have been as happy if I had to do just word puzzles or just crosswords. I liked the variety. I’m a big fan of buffets and pupu platters and things of that nature.

BW: This is definitely a smorgasbord of puzzles. Greg, how did you first hear that A.J. was writing a book about puzzles and wanted lots of new puzzles for the book?

GP: I knew of A.J. going back to The Know-It-All and the other books. Then A.J. came to the Mohonk Wonderful World of Words weekend and saw the big puzzle extravaganza that I do there. And by the end of that weekend, we were talking and he said, “I want to talk to you about this book I’m writing, and maybe you can make some puzzles for it.”

I remember, I have a whole set of documents of all the chapters that were going to be in the book, some of which made it, some of which didn’t. And we kept talking about how we were going to incorporate an original puzzle for each of these. Obviously that’s easier with the word puzzle chapters, but it’s a little more challenging with the Rubik’s Cube chapter. I wasn’t going to make a Rubik’s Cube that people had to assemble in the book. But that was part of the fun for me, getting to read the book as it was evolving, and then think, “What are the puzzles that are going to fit in with this book?” And fortunately, there was a chapter about meta-puzzles and about the Mystery Hunt, so that was the key to deciding the whole book would itself be a puzzle hunt with a meta-puzzle.

BW: You’ve got lots of experience with making puzzles for events like the Mohonk weekend. How does trying to make a puzzle suite for a book compared to that?

GP: The great advantage of doing a live event is that you can see how people are doing. And if they’re having a terrible time, I can come over and say, “Hey, this is supposed to be fun. Let me point you in the right direction.” And I can also announce to the room, “Oh, I messed up. There’s a typo in puzzle four.” There’s always a fail safe — I’m going to be there in person to fix anything that goes wrong. So it was more nerve-wracking doing this and worrying about everything. Thank God we had great test solvers, who tested everything and fact-checked everything, and, hopefully we did everything they told us to and got it all right.

I will say also, one of the things that inspires me as a puzzlemaker, and also as a creator of music, is having parameters, having constraints. So A.J. saying, “Here are the chapters that are in the book, write a puzzle for each chapter,” was an inspiration. It was a way to say, “How does all this fit together?” And of course I had to have the meta-puzzle and figure out how that worked, and then have all the answers to the meta-puzzle and match them to the chapters in interesting ways. That was the great fun of it for me.

AJJ: Originally, I said, “I’ll just make the original puzzles myself,” which was quite misguided, because as soon as I started, I was like, “This is not easy. This is an art.” It would be like, “I’m gonna design a skyscraper.” I didn’t have the skills. And so I realized very quickly that this is an art form and I better collaborate with someone immediately. And one of the great things about collaborating with Greg is that he would send the puzzles to me, and I would test them and I would enjoy him. But I was so wrapped up in writing the book, and thank God I felt so confident that the original puzzles were going to be great, and I didn’t have to worry about them.

Puzzler Hunt illustration by Joe Cabrera.

BW: A.J., how did you decide that you wanted to have a puzzle contest that went along with the book?

AJJ: I loved Masquerade [a picture book by Kit Williams with a hidden treasure hunt] as a kid, and if I’m writing a book about puzzles, I figured, how can you not have a secret puzzle in it?

And we actually went back and forth a lot of times, me and Greg and Random House and the Random House lawyers, about how we were going to do this contest. It was complicated. Originally the puzzle was going to be spread throughout the entire book, but that was complicated because legally you cannot make people buy something. And the lawyers were like, “Well, just do the contest separately.” And I said, no, I really want it to be linked because of Masquerade. So we came up with this, it’s almost a compromise. The code is in the introduction to the book, but that introduction is also available for free. And my hope is that people will like the introduction and will be like, “Even if I’m not going to win the contest, maybe I’ll buy the book.”

It went far beyond my dreams, because originally it was just going to be, you find the code and the first one to find the code wins. Then it got more complicated: what if we had four or five puzzles that they had to solve once they get the passcode? And now there are literally dozens of puzzles, and it is the most elaborate, crazy, delightful full-on puzzle hunt. And I love that, because it’s going to introduce people to this concept of puzzle hunts. And it’s also a puzzle hunt about puzzles, because the theme is puzzles and great puzzlers through history, so you’re learning about puzzles, you’re doing puzzles. It’s all very meta. And hopefully you’ll have a great time whether or not you win.

GP: We had to design something that would roll out over the course of several weeks. Eventually there is a final round that everyone who completes the first set of puzzles will be eligible for, and that will be a timed thing, but that won’t happen for several weeks. Hopefully, people get more and more involved in this thing, and then we have a group of top-notch solvers diving into the final round to win the prize.

BW: Greg, you assembled a puzzle-writing team for the contest. How did you bring that brain trust together?

GP: Some of the folks are people I’ve made puzzles with before, some of them are from my Mystery Hunt team, and others are people whose puzzles I’ve admired and always wanted to do something with. This was great fun to reach out to great constructors and say, “We want to make this thing. Would you come do this for us?” And they are — I feel like we say this at different puzzle events — but they’re the nicest people in the world. They’re smart, they’re caring, they’re thoughtful. They’re really thinking about how these puzzles play to people who’ve never done puzzles before. Will these be fun for people who are experts? You know, how diverse can we make the puzzles and the content of the puzzles? I’m going to be sad when we stop working on it, because it’s a great chance to socialize with some of my favorite people.

Even though the puzzle hunt is over, you can still check out all of the puzzles and solutions here.

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