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Wordle Editor Tracy Bennett

Why in the Wordle do we need more diversity and representation in puzzle games? In our first season 3 episode of the Art of Sway, Wordle editor and New York Times puzzle editor Tracy Bennett helps us understand the important connections between influence and puzzle-making.

Meet our guest, Tracy Bennett: Tracy Bennett is the associate puzzle editor for the New York Times and editor-in-chief at the Inkubator, a subscription-based puzzle venue. Tracy has been in charge of editing the popular online word game Wordle since November 2022. She’s had puzzles published by Knitty Magazine, the New York Times, the Los Angeles Times, Universal, Simon & Schuster, the Chronicle of Higher Education, Queer Crosswords and Women of Letters. Tracy constructed for the 2017 Indie 500 Puzzle tournament and donates puzzles to Groundcover News, a nonprofit taking action to end homelessness and poverty.

In this episode, we talked about the surprising ways that influence and puzzle-making intersect, and how puzzles can be used as a tool to connect with others and build communities around shared interests. Plus:

  • The need for a more inclusive and innovative puzzle-solving community, while also breaking down gender barriers
  • “Half of the people who solve puzzles are women, so why aren’t there more female puzzle makers?”
  • What we can learn from Wordle’s incredible social appeal
  • Why having diverse topics and themes in puzzles can help promote inclusivity and representation — and also create a more engaging and meaningful experience for players
  • For the crossword puzzle fans: why Tracy always starts with downs versus acrosses (!!)

Get ready to exercise your brain!

Tracy has crafted an original, Sway-inspired, crossword challenge for you to solve. Download the printable puzzle pdf and answers below.

Click to download puzzle

Episode 26: Tracy Bennett Transcript

Danielle Wiley: Welcome to The Art of Sway, the podcast that uncovers the power of influence and its impact on all areas of our lives. I’m your host, Danielle Wiley. Each week, we’ll explore the many facets of influence through candid conversations with industry insiders, from brand marketers to social workers, educators, leaders, and more. Let’s dive in.

Danielle Wiley: Tracy Bennett is an associate puzzle editor for the New York Times and editor-in-chief at the Inkubator, a subscription-based puzzle venue. Her crossword puzzles appear as a feature called X-Games in BUST Magazine, and she makes puzzles for the Crosswords With Friends app.

Danielle Wiley: Tracy has had puzzles published by Nitty Magazine, the New York Times, the Los Angeles Times, Universal, Simon & Schuster, the Chronicle of Higher Education, Queer Crosswords and Women of Letters. She constructed for the 2017 Indie 500 Puzzle tournament and donates puzzles to Groundcover News, a local 501(c)(3) organization taking action to end homelessness and poverty. Tracy has been in charge of editing the popular word game, Wordle since November, 2022.

Danielle Wiley: It was so great to have Tracy Bennett on. I had found out that she lives locally to me and then set about stalking her to figure out how to get her on the podcast because I am obsessed with word games. And Tracy is the editor of Wordle and also a crossword puzzle editor at the New York Times. As you’ll hear, I happen to bump into her locally and invited her on. And we had a fascinating chat. If you don’t know much about the crossword puzzle community, space, ecosystem, this is going to be illuminating. There’s probably a lot more to it than you ever knew. So, I hope everyone enjoys.

Danielle Wiley: Hi, I am so excited. Welcome, first of all, to the podcast, and thank you for dealing … I was like a total creep and completely out of character, I had just learned. So, when I met you, the day before, I had realized that you are in Ann Arbor like I am, and had been kind of trying to figure out how to reach out to you to invite you on the podcast because I’m a huge fan of Wordle and really all of the New York Times word games.

Danielle Wiley: And then I was at the grocery store doing a taste testing of alcohol-free spirits. And I saw you in your Spelling Bee cap and accosted you, I’m very shy in public and meeting people, but I don’t know what came over me and I accosted you and somehow didn’t completely freak you out, and here you are. So, welcome.

Tracy Bennett: No. I was glad you did. I’m glad to be here. Thank you for having me on the show.

Danielle Wiley: Yeah. It’s great. For those who don’t know, you are the editor of Wordle, which has kind of taken everyone by storm. I don’t think I know anyone who doesn’t play, maybe my weird brother, but other than that. So, I’d love to hear just a little bit about your journey, because I know you didn’t start out working in the crossword and word game space.

Tracy Bennett: That’s correct. That’s correct. Well, I mean, I’ve always been into puzzles ever since I was a child. I was voraciously solving like jigsaw puzzles when I was very little. And always loved word games, Highlights, the magazine Highlights. I was very into that. And I always just sought out in the newspaper the section where they have the jumble and compare the pictures and find the differences and things like that.

Tracy Bennett: So, always been kind of my bag. But over the course of my life, I have been more of focusing on reading and studying English literature and things like that. So, I have an English literature degree from the University of Michigan.

Danielle Wiley: So, you got the degree, and presumably you stayed in Ann Arbor?

Tracy Bennett: That’s correct.

Danielle Wiley: But it was so amazing that you couldn’t leave-

Tracy Bennett: I grew up in Maine and came here for my sophomore year, transferred from the University of Southern Maine, where I was actually a theater major. So, there was some part of me that was interested in being an actress. I was too shy to even try out for plays. So, my first year, my freshman year, I just took classes like Shakespeare and things like that, the more academic ones, and was too afraid to go to any tryout. And I kind of figured out that that wasn’t really for me. So, I switched to being an English literature major and also transferred to the University of Michigan, where my sister Cinda Hocking was already attending.

Danielle Wiley: So then after that, you had a whole other career really before this whole New York Times gig?

Tracy Bennett: Yeah. So, I mean, I was a student of English literature, but I was starting to figure out in my junior and senior year is when I was working on a thesis. I was in the honors program in English and more and more, I was writing papers that were about, not about literary theory or the historical context of book that I was reading, but how the paragraphs were working and how the sentences were working and how the word choices conveyed what the writer was trying to say?

Tracy Bennett: And it turns out, I was also really interested in foreign languages, and I was studying Spanish really intensively as well, that my real interest was linguistics rather than purely literature or theory. And so, if I had gone on and done a master’s or gone on for a PhD, I would’ve switched to linguistics. And I was figuring that out by the time I was a senior.

Tracy Bennett: But I also didn’t want to keep being an academic. I wanted to be in the real world working and I was really interested in publishing. But the work that I actually got right after college was secretarial. And I actually did enjoy that. Secretarial work, there’s a lot of sorting and actually using words and helping edit.

Danielle Wiley: I loved it. I temp all through college because I’m a very fast typer, I think from my years of piano and I love doing that and just having this set thing that I could organize and get done and then move, very satisfying. Yeah.

Tracy Bennett: And I also worked at the hospital because I had how you do work study. Well, some people do work study in college. I did work study and I got placed at a job at the hospital. So then, I was also doing, I worked at the blood gas lab overnight, their night shift. And I did some more scientific things, but everything that I did and appealed to some working with details, which I really love to do, and analyzing things and sorting things and keeping track of things is kind of like my vibe.

Danielle Wiley: Yeah. So, you did that and then you went into secretarial?

Tracy Bennett: Okay. Yeah. Secretarial. And I did that for a couple of years. I was starting to feel like I really wanted to use more of my degree. I really wanted to work with words in a more intensive way, like for a publisher, but I didn’t know where to go in Ann Arbor for something like that. And I was in a relationship. I wasn’t going to leave and move to New York City or Boston or something.

Tracy Bennett: So, I was just at a party and somebody at the party said, I said this to them in just kind of casual conversation when we were talking about work. And he said, “Oh, I work at mathematical reviews and there, it’s really fun and interesting and they’re looking for copy editors.” And I was like, “Yeah. I’ll just toss in my application.” And I got interviewed and I got hired.

Tracy Bennett: And it was quite a learning curve there because I never was very comfortable with mathematics. I did algebra, but I didn’t go any further than that. And this is higher level postgraduate level mathematics, way beyond my abilities to understand. So, it hit me a year to do the job well, six months to even be competent. It really is a language. And that’s how someone like me would need to approach a job like this.

Tracy Bennett: So, I’ve learned how to read equations like sentences. Sometimes a variable may be a noun, sometimes an expression like A equals two, for example, the equals is the verb. And there’s a subject and there’s an object.

Danielle Wiley: Fascinating.

Tracy Bennett: And then you’ve got to deal with punctuation around that. But also, that whole expression can be a noun in a bigger sentence, larger equation, or within words, English words.

Danielle Wiley: My son is starting at Michigan next year and majoring in math and does not love reading. And so, I feel like I’m going to force him to listen to this conversation so that he can see the connection.

Tracy Bennett: Yeah, oh yeah. And math is just like, it’s actually quite a beautiful language. And what is cool about it is that it’s a language that everyone who speaks different other languages can actually understand. So, if you write an equation, anyone who speaks any language can also speak that language. It’s almost like translatable and very pure. It’s very pure.

Tracy Bennett: But I also learned there too, so we had a lot of foreign languages that we had to process in the course of publishing. They were called reviewers, people who wrote the reviews for mathematical reviews. They were all over the world and spoke many different languages. So, the English might be a little bit choppy or unclear. And so, part of our jobs was to make it clearer.

Tracy Bennett: So, understanding how other languages are structured really helped me to be able to determine what they were trying to say. Also, we were intaking just titles and dealing with translations of titles. So, I taught myself to read Cyrillic and it was very similar because I didn’t necessarily understand the word, but I could sound it out so phonetically I could sound out all the Cyrillic letters. And then I could also proofread them to make sure nothing was mistranscribed, mis-transliterated, that’s the word. So, I learned a lot in that job, and I really got me heavily into details, which I absolutely loved.

Danielle Wiley: That’s awesome. And so, how did you make the transition from that to the New York Times puzzle?

Tracy Bennett: Well, I was there for 30 years. I stayed at [inaudible 00:11:06] for 30 years. So, when I started at Math review, I took a cut in pay from a secretarial job because it was what I wanted to do. And I think that is part of the story of my life, is that I always stuck with or followed my heart and stuck with the things that I love.

Tracy Bennett: So, when I found something that really satisfied, I didn’t know my passions, my vibe, whatever, when I found something that really, really felt good to do, I was like, I knew I wasn’t going to do something else. I wasn’t going to do work I didn’t like, even if it’s paid less and I had to live a college student for the rest of my life, I was going to [inaudible 00:11:49].

Danielle Wiley: You’re in the right town to do it.

Tracy Bennett: Yeah. So, I did stay there for 30 years. I was there for five years before I became manager of the department. And that was a big change. I actually had to stop doing the work that I love every day. But I did reward myself on Fridays by copy editing most of Fridays. But there was a lot of personnel management and dealing and developing people skills. We had people management skills.

Tracy Bennett: And that I can say that I got good at it, but I never loved it. That was never satisfying to my soul. One of the things that came out of that is that I really enjoyed my hobbies outside of work. And one of my hobbies was solving puzzles, particularly crossword puzzles.

Tracy Bennett: I always solved this Sunday New York Times puzzle since I was 17 years old. I mean, with a few breaks here and there, and especially at difficult times in my life at certain, during a breakup, I was with someone for 13 years, and when that was breaking up, I definitely got into puzzles big time. So, I would buy a whole book and just solve a puzzle every day. So, it’s always been kind of a soothing resource for my wellbeing in addition to just really satisfying my analytical and puzzling soul.

Danielle Wiley: Well, so I mean I’m so convinced that it’s so good for you. I mean, my grandmother solved the Sunday puzzle till the week she died at 99. I mean, she couldn’t walk. She was in a nursing home, but she did that puzzle every single week.

Tracy Bennett: That was my great-Aunt Kay. She was my grandmother’s sister. I actually inherited all of her crossword puzzle dictionaries. And of course, we don’t really use those anymore because we have the web. Google everything now. But she was dedicated Sunday New York Times puzzle, and we had that in common, and I always felt like a kind of soul connected to her in that way, because nobody else in my family was really that way, except me.

Danielle Wiley: So, you loved puzzles and had always done them. And then so you 30 years at mathematical review?

Tracy Bennett: Right. But at the 20-year mark, there was something at the Ann Arbor News where they had a competition. It wasn’t a tournament, but it was a puzzle solving competition. And I thought, I’m just going to walk down to the Ann Arbor News headquarters where they were doing the contest and it was self-directed. So, you didn’t have to sit in the same room with people and solve together, but you could go and check in, get your puzzle, and be timed, and then turn it in at the end.

Tracy Bennett: So, I did that and I won, and I won by a lot on time, but I had one square wrong, and the person who came in second was perfect. That has bothered me for the last 10 years, but it still was inspiring. I had a friend and coworker, Lisa Nichols encouraged me to go to the American Crossword Puzzle Tournament, which I did the next time it was available to go to.

Tracy Bennett: Well, first I watched Wordplay, the documentary about the American Crossword Puzzle Tournament, got really excited, and I was thinking of myself as a competitor. So, I went to the ACPT as it’s called, for short. At that time, it was in Brooklyn, started out in Stanford, Connecticut, moved to Brooklyn for a while when it got really big after the Wordplay documentary came out, it’s now back at Stanford. So, it’s kind of had an arc.

Tracy Bennett: But at that time, it was in Brooklyn. So, I was going to the big city. I had a young child at home, Daniel, my son. So, I was kind of leaving him for a few days for the first time, getting some time on my own and exploring a side of myself that I hadn’t really explored.

Tracy Bennett: Am I a competitor in crossword puzzles? I did find out that I’m not that competitive. I thought I would be, but the people who really are competitive, they don’t even really read all the clues. So, they only do the downs, and then they may just make sure that the crosses look like they make sense. So, it’s about winning. It’s not about-

Danielle Wiley: And wait. This is so fascinating. It has nothing to do with influence or anything we’re talking about, but why would you start with downs versus crosses?

Tracy Bennett: I believe that it’s because most of the time the theme of a crossword puzzle is in the crosses. So, the theme-

Danielle Wiley: I was just thinking about that this morning, that [inaudible 00:16:55].

Tracy Bennett: You would be distracted.

Danielle Wiley: Okay. Interesting.

Tracy Bennett: Yeah. So, I was in the lowest division, halfway up the lowest division. There were six divisions when I finished in that contest. I didn’t even finish two puzzles in time. So, I kind of quickly realized that wasn’t going to be my thing. I did compete for the following two years, but more for fun, not in a serious way. It’s just fun to be there with my tribe, which is really the most significant part. I found my people when I went to the tournament. Within 10 minutes of being there, I was like, “Oh, these are my people.” And it was just incredible.

Tracy Bennett: And in the process, I also met people who make puzzles because a lot of them go to these events, and some of them are officials, which I am now. I’m an official at the ACPT every year. And so, that’s more of an overseeing, helping the whole thing go well.

Tracy Bennett: So, I found a mentor in puzzle making there, and I kind of switched gears from competing to making. And that was definitely a magical moment for me because I just got more and more involved after that. And it started to take over more and more of my life. Every year, I was doing more and more of it.

Danielle Wiley: And it’s hard. I mean, I’ve always loved crossword puzzles and mid-COVID, my brother-in-law and I were like, we’re going to make a puzzle and he’s way faster than I am. And I said, “We’re going to make a puzzle together. We’re going to do a Thursday. I have an idea.” And we downloaded the software, and I took a class, like an online class with Ross Trudeau.

Tracy Bennett: Oh, excellent.

Danielle Wiley: It’s free. It was wonderful. And I was like, this is what I’m going to do. And the class was great, and then I sat down to try to do it, and I was like, “This is too hard.” It’s hard to make puzzles.

Tracy Bennett: Yeah, yeah. Definitely took me, I would say it took me a year to really be able to submit puzzles that would get accepted by a publication. And a lot of the first puzzles that I submitted were co-authored. I didn’t feel comfortable doing my own for a while. So, yeah, it was actually similar to learning at math reviews, how to deal with math. I mean, it was a process.

And there are four areas of learning, it’s not just one thing. I mean, there’s developing a theme, which actually is, I think the hardest, developing a tight, concise, meaningful, and funny theme. It’s very hard. And then making the grid, placing your theme, and I don’t know if you know this, you probably do because you took class, but usually a theme is placed symmetrically within a grid, and that grids have symmetry. So, the black squares are symmetrical. So, learning how to make a grid, fill a grid well, not full of junkie, crappy words that nobody knows, and then writing clues. So, there’s quite a process as you know.

Danielle Wiley: And I want to get back to the working with a collaborator and how that whole community works, but just quickly to finish up the story. So, you started creating puzzles, and how did that transition to actually becoming your day job?

Tracy Bennett: So, my very first puzzle was commissioned, and that was by Nitty Magazine, and that was fun. And I learned a few things in that process because I had a grid with a typo in it, and I found it out the day before I was about to send the files. Since learned to call that every time it happens, which isn’t that often fortunately. My bottelier moment, and I call it a bottelier moment when you make a really stupid mistake like that, because I misspelled bottelier, and that was a knitting pattern. I mean, it was part of the theme.

Tracy Bennett: So, there was that. So, that was a learning curve. I was starting to submit to the Times and other places. I got lots of rejections, which everybody does because the Times gets 200 puzzle submissions weekly, and they can choose seven of those. So, the norm is that you don’t get your puzzle chosen. But I would take those puzzles and resubmit them to other venues. And I got two puzzles published in The Chronicle of Higher Education, which is pretty cool, because that’s like an academic, it has an academic connection, and I liked it. I also got one in the LA Times, I think before I got one in the Times.

Tracy Bennett: So, I finally, I think with my 13th submission, my 12th through 13th submission, got one accepted. And the magic was that it was a Sunday, which was my favorite kind of puzzle. And they’re very hard to make. They’re twice as hard to make really. It’s really hard to come up with seven to nine really good theme answers. And these were artist puns. They’re kind of groaners. I’m actually still surprised because we say no to a lot of groaner pun puzzles, but it would be with flying collars instead of with flying colors and smoke and mirrors.

Danielle Wiley: Got it.

Tracy Bennett: And the clues were pretty funny. I can’t remember them at the time now, but they were funny. And it was very exciting. And really, once that happened, I felt like, this is it. I’m like, this is something I do outside of my day job, and it’s something that is fulfilling to the max. It’s just exactly what I want to be doing. It’s not beside what I want to be doing or adjacent or similar, but it is the thing that I wanted to.

Tracy Bennett: And as time went on, so after that puzzle came out, Deb Amlen, who was the editor and writer of Wordplay, not the documentary, but it’s a New York Times specific blog about the puzzle, the daily puzzle. And she was also had the byline at BUST Magazine, which is a feminist publication, used to be six times a year, and now it’s quarterly.

Tracy Bennett: And so, BUST Magazine, she was working for them, making a puzzle called X Files. It’s a little bit sexy. It usually has a sexy theme. But she was overloaded. She had a lot of work on her plate. And so, she was looking for someone to take that byline to make that puzzle. And she wanted to give it to somebody who was new, someone who could use it as a way to get better at the craft and also, someone who was interested in the issue of women in puzzles and the issues around … Because the BUST Magazine puzzle is definitely more progressive feminist and boundary pushing.

Tracy Bennett: So, I had already been making a little bit of noise in the community because it was really clear that there were very few women in the field making puzzles and a lot of men. And so, there are various forums and blogs where people discuss these things. And I was on there discussing these things. So, she was also aware that I was talking about these things. So, I seemed like a good candidate. So, she approached me and one other person, Anna Shechtman, who’s also, she was new at the time, she had been interning with Will Shortz, actually, she was one of the few female interns that he is had just, I started making the BUST puzzle.

Tracy Bennett: And that was also another opportunity for me to have regular work doing and creating puzzles. Because when you’re just creating puzzles and submitting them on spec, it can get really discouraging because you do get a lot of rejections, even for good puzzles. And so, you want to have a chance to have your work be seen and commented on or experienced by others, get feedback. And the only way to really do that is to get it published.

Tracy Bennett: I decide, because they don’t really have puzzle editors at BUST, they have great editors, but not specific to puzzle editing, which is a specialized talent that you definitely can’t just transfer skills from prose editing. There’re a lot of little rules for clues. So, I asked my friend and a colleague, Lisa Nichols, to be my test solver, and I paid her in lattes. So, every time she tested a puzzle for me and gave me feedback, I would buy her a latte.

Tracy Bennett: And she was great because she is very highly literate. She’s also an English major, and she was and really, really avid reader and likes games, loves Boggle and Scrabble and everything like that. But her experience with solving puzzles, she wasn’t like a veteran or super, super into it. So, she’s the kind of person who I hope would be solving the best puzzle, someone who wants to do a puzzle but casually and who doesn’t already know crossword ease.

Tracy Bennett: So, all those things that appear in puzzles that are kind of glue holding the better answers together, but they’re weird words that people don’t use in real life, or they’re really obscure rivers and some far-off region that no one really has memorized. So, words like etui, epee, just various things like that are [inaudible 00:27:02]-

Danielle Wiley: I know epee very well because of Spelling Bee. It’s in there today.

Tracy Bennett: And even Oreo, even though it’s a regular word that people use, it’s so overused in puzzles.

Danielle Wiley: Or Sia is the one that I’m sure makes my dad crazy because he’s a puzzle solver and at 81 is not super familiar with Sia.

Tracy Bennett: And she definitely would spot things that I missed. So, she would see, I had oater, O-A-T-E-R in one of my early puzzles. She’s like, “What the heck is that?” And I’m like, “Well, if you’d saw puzzles every day, you would know it was a Western film. It’s an old term for a Western movie.” So, I would change that. I would say regular solvers don’t actually encounter the word “oater” every day.

Tracy Bennett: But she would also spot things that would uncover my hidden biases. Even I considering myself to be a feminist and progressive, but sometimes have something in there that was a total assumption or something that I hadn’t considered someone’s point of view, who was more marginalized than I. She was really good with that too. And it really helped me become sensitive to those issues in my own work, even the stuff that I was sending out to the mainstream publishers. So, she was great. And that really helped me develop my skills.

Tracy Bennett: And then Laura Bronstein, now, I was very experienced in doing a lot of work and still being very vocal about the issues of women in puzzles. And Laura Bronstein, who was also pretty new to puzzle making, reached out to me and we decided to have a kickstarter and try to start our own publication for puzzles made by women, not for women, for everybody, but puzzles made by women and non-binary constructors. And that is called the Inkubator with a K, and I-N-K.

Tracy Bennett: And we have been publishing, we’re in our fifth year. This is our last year. We have recently announced that we have a desire to get some of our life’s back, some of our downtime. She has younger kids at home, so for her especially she wants balanced, but so do I. But we have devotedly worked on this project for four or five years and introduced a lot of new women to the field, published a lot of women for the first time, and non-binary constructors for the first time. And featured some work by veteran puzzle makers, women who maybe haven’t had a chance to explore more progressive themes or more edgy themes or more feminist themes.

Tracy Bennett: So, the Inkubator is also a place where you can have more of your authentic voice come through and not be edited in a mainstream way. So, this nice and indie, what we call an indie. Yeah. So, there’s a lot more freedom to have your personality come through in the puzzles as a puzzle maker.

Danielle Wiley: I think it was so amazing to me and kind of like a aha thing, just the lack of diversity that had been within the puzzle making space. I mean, of course that has to have an impact on what the clues are and how it all works, and who’s able to solve and who’s part of the community.

Tracy Bennett: Well, if you don’t see yourself in a puzzle, and that’s one of the lessons I learned, even with my own thinking, I’m progressive when I’m making puzzles and having Lisa point out things that I’m not seeing. If you are not seeing yourself in the puzzle, why would you go and do another one? What would inspire you to continue to solve puzzles? And especially if they only seem to be around the interests of a very narrow, small group.

Tracy Bennett: So, even for the interests of the future of puzzles, the more people that can be brought into the joy and fun of solving, the more lively and the more even profitable this is going to be.

Danielle Wiley: Yeah. It just broadens the reach of it.

Tracy Bennett: Yeah. So, one of the things that kind of got me angry when I was getting a lot of rejections when I was first trying to get published, I saw XWord Info is a database and a website that has a lot of statistics. They put out a lot of statistics about puzzles, the New York Times puzzle specifically.

Danielle Wiley: So, it’s all the words that have been in there, correct?

Tracy Bennett: Right. It’s all that, but it’s also demographic data. And you can see all of the constructors. There’s a lot of different kinds of data that they compile and present. How many Schrödinger puzzles have there been? How many puzzles with unusual symmetry have there been? They have a lot of data.

Tracy Bennett: And every year, they would say congratulations to the debut constructors. And the year that I was still trying to get debuted, and I hadn’t been debuted yet, there was an announcement. Congratulations to the 30 men and six women, something like that, 32 men, six women, I don’t remember the exact number, but it was like that, who debuted puzzles in the Times. And I’m like, wow. I think it was even less than six. I think it was like three, but it was somewhere under 10. And it was just the scale of the difference really, really struck me.

Tracy Bennett: And I’m like, there’s something not right here. It doesn’t seem like that would happen naturally. You know what I’m saying? And especially half the people who solve puzzles are women. So, why are so few women making them? But it isn’t the case that it was always that way. So, it’s not actually traditionally that it’s been male dominated.

Tracy Bennett: When they first became a craze puzzles and people were competing, the first winners were women. So, the first women at these competitions were women. Now they’re mostly men and Margaret Farrar. Margaret, she was the first New York Times right puzzle editor. And she was there for quite a few years. And until the ’90s, the split between women and men making puzzles more like 40-60. So, 40%-60%. There were a lot more women making puzzles for many years.

Danielle Wiley: And then, not to get too controversial, how did that tank so dramatically?

Tracy Bennett: I actually don’t know. I think there’s a combination. There’s never one thing for something like this, but I do think there was more, not so much that fewer women were making it but more men were entering the field. Because a number of people making puzzles in general exploded. So, it used to be a really niche skill with not that many people and very familiar names making puzzles. And so, it was just much smaller community.

Tracy Bennett: And then when puzzle software, puzzle making software became available, and you weren’t doing it by hand on a grid on graph paper with pencil and doing this kind of detailed, almost craft like work, and instead you were pushing buttons and filling spaces and developing wordless and algorithms, it became more accessible to more people to try it, to figure out how to make a puzzle without having to draw on graph paper. And so, I think that was part of it, that just there was an explosion of people entering the field, and many of those people happen to be men.

Danielle Wiley: Right. Well, and there’s not something that interests me a lot is when in anything. So, I mean, when I’m looking at podcast guests or we’re putting together a PowerPoint for clients and selecting photos for it, you’re never going to accidentally end up with diversity. It has to be purposeful. And I think a lot of people kind of bristle at that because it feels, I don’t know, affirmative action and it feels artificial. But that’s really the only way to make change.

Tracy Bennett: No, really, it is the only way. It is. And that is another point to make. Because that at that time in the ’90s, all of the editors of the major publications producing puzzles were men. And they were older men, men who had been in the field for a long time. And that situation has changed quite a bit in the last five years even.

Tracy Bennett: And that’s not even bringing up the issue of race, which I mean, it’s really predominantly white field of creating puzzles. There have been some initiatives made in various places. USA Today, for example, now has a biracial young guy at the helm, Erik Agard, also a phenomenal competitor at the ACPT. He’s won a couple of times and he’s amazing.

Danielle Wiley: I recognize his name as a constructor.

Tracy Bennett: Yeah. He’s an amazing human being. But he has demonstrated a lot of what’s possible. He doesn’t take puzzles on spec. He has a set group of people making puzzles. So, he chooses who he wants to make puzzles. And he has incredible ethnic diversity and gender diversity. And he’s shown that you can do this if you make an effort. You can make puzzles more diverse. And he’s broken a few rules of puzzle construction too, that the rest of us are still afraid to do. He does not require symmetry.

Danielle Wiley: I know that’s a very controversial in the crossword. I feel like half the people listening to this are going to be like, what are you guys talking about. But people take it very seriously.

Tracy Bennett: They do. And there’s a really young fellow, David Steinberg, in charge of Universal puzzles, and he’s also made some strides. And then big news, Patti Varol is now in charge at the LA Times or the Los Angeles Times. Rich Norris was a great editor and was there for many, many years, but he recently retired, and she is only the second woman to be an editor of a major mainstream puzzle since Margaret Farrar. And this is amazing. I mean, it felt so good. I was celebrating when she got named.

Danielle Wiley: That’s awesome.

Tracy Bennett: And then at the Times, Wyna, Wyna Liu and I were hired two years ago, and that totally changed the balance, the gender balance at the Times. And then we recently hired Christina Iverson, who’s another talented constructor. So, now we’re a team that’s pretty balanced that way.

Danielle Wiley: Yeah, Okay. There’s still change that can happen.

Tracy Bennett: But Wyna is the only person of color. So, there’s still that. But yeah, there’s a lot of work to do. There’s a lot of work to do. And we do have a diversity fellowship now that has been instituted. And we’re in our second season, so we had five fellows last season, and all of them got published. They had debut puzzles published.

Danielle Wiley: That’s great. So, one of the things that really interests me just in terms of how people who have been in the space can have influence on changing this and bringing in more constructors. We talked a little bit before about people partnering up. And I know Ross Trudeau is like, I’ve seen a lot of what he does about providing free mentorship to anyone who’s a woman or of color to try to make a change there. And I think that I love seeing that, and I love seeing that anyone who has some kind of expertise can have influence on the industry as a whole by just putting themselves out there and offering that up.

Tracy Bennett: I mean, sometimes all you need to keep going because it is a field, just short story writing or art where it’s really hard to break in. And even when you’ve broken in and it’s really hard to get published in regular way because of the number of people submitting work. So, even just hearing that this is normal, don’t get discouraged. Even just saying, you move on and you go to the next puzzle, you send the next one in, you don’t wallow.

Tracy Bennett: Because I think a lot of people, if they got rejected once or twice, would be like, oh, I’m just not good at this. And I think there’s some people who tend to do that more than others. Have the confidence to persist in the face of rejection. Sometimes you just need someone to tell you, this is normal and keep going.

Danielle Wiley: Yeah. You need a buddy. I mean, there’s a reason why, I don’t know, even at colleges, they connect you with older students who’ve been there, or I mean, they do that at high schools too, or in any field or any situation, it’s always helpful to have a buddy who’s been there and done that. Yeah. Very cool. So, we did not talk about Wordle.

Tracy Bennett: Oh my god.

Danielle Wiley: Which is okay.

Tracy Bennett: I mean, we have to finish, right?

Danielle Wiley: Yeah. Well, I just quickly just to kind of tie it all together, I mean, I certainly see it a game, like Wordle, one of the things that’s so beautiful to me about it is it brings people in to this broader ecosystem of games, just the sheer number of people who feel like, oh, that’s doable, and I can do it. And then maybe you try a Mini crossword, or you play around the Spelling Bee, or it’s a gateway drug, right?

Tracy Bennett: Right. And the whole suite of New York Times games like Spelling Bee and Mini, they’re very digestible and they’re puzzles that can be played within 10 minutes, maybe the Spelling Bee, you do it at little portions.

Danielle Wiley: I was going to say, not in life, my family, it’s like cutthroat who’s going to get Queen Bee.

Tracy Bennett: But the rule is just really, really digestible. It’s much less intimidating than a crossword puzzle, but it’s simple, but it isn’t easy. You do need to use strategy and also a little bit of luck to get the answer. So, I think it’s just the right amount of challenge and fun that it doesn’t take your whole day. And the shareability of it, I mean, it actually became during the pandemic, a way for people to touch base every day with their friends and loved ones in a kind of fun way. The shareability without spoilers was a really kind of genius.

Danielle Wiley: Yeah. It’s funny, I have a Spelling Bee group text message with my dad and stepmom and aunt and husband and sister and brother-in-law, and then we have a Wordle one, and I had forgotten to submit my Wordle score a couple of months. I was like, I don’t know what was going on. Work was busy, something. And my dad called me early afternoon, he’s like, “Are you okay? Is everything okay?” And I was like, “I’m fine.”

Tracy Bennett: Because you didn’t do your…

Danielle Wiley: What the heck. And I didn’t submit my Wordle score. He was like terrified or something was drastically wrong with me.

Tracy Bennett: Yeah. And there was that case of that woman who was being held hostage.

Danielle Wiley: Oh, that’s right. Yeah.

Tracy Bennett: They looked in on her because she hadn’t done her Wordle. This is crazy but it’s wonderful.

Danielle Wiley: That’s so amazing. Yeah. That’s very cool. So, again, I could talk to you next time I see you at the grocery store. We’ll talk more about all this stuff.

Tracy Bennett: I’m sorry we didn’t do the Wordle.

Danielle Wiley: Oh, no, I’m actually more … I mean, I love Wordle, but I’m much more passionate about Spelling Bee and crossword puzzle. So, this was delightful for me and I loved it, but I want it. So, season three is dedicated to women 50 plus because I’m turning 50 this year and very proud of it.

Tracy Bennett: Happy birthday!

Danielle Wiley: Thank you and want to kind of celebrate. So, we have this one question that we’re going to ask everyone who’s on this season, which is one woman who’s just really influenced you in your life and your work and has just had a big impact on you.

Tracy Bennett: This is probably a common answer, at least I hope it is. But it’s my mom, my mom Linda Townsend. So, she raised us in the ’70s. She kind of liberated herself from being a Navy wife to being an artist. And so, she was like activist, an artist in the 1970s. She moved around the state of Maine so that we could get an alternative, my sister and I could get an alternative school education, which the public schools in Maine are fine, but they weren’t great, and she wanted us to have really good education.

Tracy Bennett: It was child led and really magical. I had really good teachers, and I had a five to one student teacher ratio, which is almost unheard of, and was really, really fundamental to my development. But also, she just modeled. She modeled what it was to follow your dream and to be true to yourself, authentic to who you are, even if it’s uncomfortable, and even if it causes people to go against you. So, I mean, I think she’s been an inspiration my whole life.

Danielle Wiley: That’s wonderful. That’s great. Well, thank you so much again. This has been just a delight.

Tracy Bennett: Yeah. Thank you, Danielle.

Danielle Wiley: And I love having you on. Thank you for sharing everything.

Tracy Bennett: Thanks.

Danielle Wiley: Thank you for listening. Don’t forget to like, share and subscribe. Please check back next Monday for a new episode featuring marketing conversations through the lens of influence. I am your host, Danielle Wiley, and this is The Art of Sway.