Work Friends is our interview series that digs into the complicated realities of people with interesting jobs.

In the beginning of a crossword puzzle creator’s career most of the work is done “on spec”. This means that a fledgling constructor (constructor being their technical title) could create dozens or hundreds of complete puzzles and submit them to editors without pay for years in hopes of getting even one chosen for publication. At The New York Times, for example, Tracy Bennett tells me that there are hundreds of puzzles submitted on spec every week, most of which are rejected. For years Bennett herself suffered these rejection emails, the same ones she would later be responsible for writing. Until finally, in 2013, after years of spec work, she got a puzzle published in the vaunted New York Times Sunday Magazine.

The Sunday Times was her “first love” of crosswords, an affair she discovered as a teen who would get the puzzle from her wealthier friends whose families were subscribers of the magazine. Even before crosswords, though, Bennett loved letters and words. As a child she says she actually enjoyed spelling tests. When she tells me this over Zoom I imagine a young bespectacled Bennett at her school desk daydreaming in word play; anagrams, palindromes, and little puns doodled in the margins of her notebooks. In hindsight, her current vocation as a puzzle editor and constructor — most notably as the editor of Wordle at The New York Times, but also as a contributing columnist at Bust and constructor Crosswords with Friends — seems fated. In reality, it took some serious work. 

For 30 years Bennett worked as a managing copy editor at Mathematical Reviews/MathSciNet and, as she put it, she was “happy to stay there forever.” But during her tenure she was actively diving deeper into the world of puzzles. At first, just as a solver, occasionally participating in competitions like the famed American Crossword Puzzle Tournament (the subject of the popular 2006 documentary, Wordplay, which, according to Bennett, “makes crossword puzzles look very thrilling.”). But after reaching a ceiling in competition (“I got in third place in [the lowest Division, E] and was like, ‘That’s as good as I’m going to do.’”) Bennett decided to explore puzzle construction, and began to regularly read puzzle blogs like Rex Parker and Xword Info, and sought out the mentorship of Vic Fleming, a notable constructor who once co-created a crossword with President Bill Clinton.

With this support Bennet’s career slowly picked up steam. She was published more frequently, got hired in paid constructor roles, and launched a puzzle publication and service called Inkubator with fellow constructor Laura Braunstein, which focuses on dismantling the gender gap in puzzle making by publishing and mentoring new women and non-binary constructors. Today, Bennett brings all of this experience to her day job as the wizard behind Wordle. Read on for our full interview with Tracy Bennett where she shares her experience in puzzles and perspective on making her work into play.

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Sydney Allen-Ash, Co-Editor of Early Magazine: How did you first get interested in puzzles?

Tracy Bennett, Associate Puzzle Editor at The New York Times: It all started when I was a teenager and I got snowed in with a friend of mine who was dog-sitting in Vermont. I was there for three days with my friend and her boyfriend, so they were keeping themselves occupied. In this house the family had a whole stack of the New York Times Sunday Magazine and I was so bored that I started to try to solve one, that really got me hooked. It took me two to three days to finish it but that was the first time I really saw a beautifully-rendered fun theme in the crossword, in addition to just the challenge of solving it.

I was just like, “Oh my God, this is an art form. This is more than just solving the puzzle. Somebody has created something beautiful. Something really funny.” And that sparked my love for the crossword puzzle. I was an addicted solver after that, every Sunday.

The other thing that happened was that these synchronicities were starting to occur. I had a boyfriend before I went to college and his last name was Eddy. One night, I’m lying in bed with him doing the crossword and I got this clue “whirlpool” and I'm like, “What is this?” And he's pointing to himself and I’m like, “Oh, it’s an eddy!” There’s nothing majorly significant about that moment but, for some reason, I knew that I would always remember it. This was a little moment that stood still. 

Then years and years later, I was lying in bed with Mike, a man I was with for 13 years, and I'm doing a puzzle. And I say, “What is Madras?” And he's like, “That's impossible. I was just reading the word Madras in my book.” He reads the sentence out and it turns out Madras is a city and a type of fabric. So, that was interesting. And then decades later I’m laying in bed with my late husband, George, and he's watching TV and I'm solving a puzzle. And I say, “What is the name of Eddie Murphy's character in Coming to America?” and he pointed to the screen and that was the movie that was playing! And Eddie Murphy’s character is just walking in and says, “I am Hakeem.”

It's just ridiculous, right? These are the kinds of things that were happening. And so I started to have a mystical feeling about puzzles. It felt like I just needed to keep doing it, so I did.

Syd: How did it feel when you finally got hired by The New York Times, the publication you were gunning for forever?

Tracy: It was literally a dream come true. It's a privilege to do what you love for a living.

Syd: Do you still love it? It doesn’t feel like a slog?

Tracy: Yeah, I love it. There are sloggy elements but I've lived long enough that I know every job has tedious bits. I'll tell you what the tedious elements are, it's reviewing the 200 puzzle submissions that come in every week and having to say no to most of them. That's a big job. You know, just writing the no’s. Even if you use a template you always want to add a little something because you were in that position of receiving those rejections before.

Syd: You know what it feels like. What year was that when you started at The Times, 2020?

Tracy: I started as an associate puzzle editor in September 2020 at The Times. And when I started they said I would get a game at some point. They were designing games in-house like Spelling Bee, The Mini and Letter Boxed. And then Wordle got acquired like a year later and I was actually surprised when they said, “We think you should take it [on as the editor].” 

Syd:  Why were you surprised?

Tracy: I guess I just figured that it’s such a big game, that they would give it to someone who already had a game and knew how to do that. But I didn't realize that it would be really different being an editor of Wordle than it would be being editor of Spelling Bee, or the Mini or another game that was created in-house. But it really is. 

First of all, because Wordle didn't have a byline on it and then it did. It was also created by someone else. And it was huge. I mean, worldwide, tens of millions of people were playing the game. And people have feelings about The Times having acquired it. 

Syd: I was surprised by the dramatic reaction people had to the announcement of your role as Editor of Wordle, there were hundreds of comments in that post alone. I guess because puzzles for me, like most people, are such a solitary experience. I didn't think about how other people felt about them and I was so surprised that people had such a strong reaction. Were you exposed to any of the negative feedback? How did you respond?

Tracy: I didn't find a lot of that negative feedback because I didn't seek it out. I don't twitter much, I’m not there. So I feel I was far away from it when the announcement first went out. And then I was really distracted because locally I was getting a lot of attention. The Channel Four News van showed up at my house the next day and I was getting a whole flurry of people asking for interviews.

So, I didn't get people's comments about the announcement, but I did when the “feast” fiasco happened..

Syd: Right, the “feast”.

Tracy: That's when I kind of had a freak out about feedback.

[Editor’s Note: For those unaware of Wordle’s dramatics, on Thursday, November 23rd, 2022 — American Thanksgiving — Wordle’s word of the day was “feast”. This on-the-nose reference was, in the loudly-voiced opinion of Wordle’s devotees, Tracy’s first big blunder as Wordle’s new editor and, in their minds, foreshadowing of the game’s demise.] 

Syd: Walk me through the process, how did “feast” happen?

Tracy: All the words that appeared in November 2022 were my picks and I was probably working on those like six weeks ahead. So, six weeks earlier I was starting to set up Wordle and the list of words. I hadn’t settled on any kind of a process yet for picking the words. And another factor was that my supervisor, Joel Fagliano, who was helping me with Wordle early on, went on paternity leave. I didn't want to bother him so I was like, “I'm gonna figure out how to do this on my own. I'm just gonna try this random selection method.”

Syd: Yeah. Just throw a bunch of stuff at the wall and see what happens.

Tracy: The first word I picked was “begin”, and that was intentional, but I was encouraged to do that. I had a different word and then our team was like, “You should choose a significant word for your first day,” so I did.

Syd:  Okay, yeah.

Tracy: That was thematic. But then it wasn't thematic again until Thanksgiving week, when I had picked “drive” [on November 22nd, the day before Thanksgiving, referencing one of the busiest travel days of the year in the U.S.]. And, I mean, it was really a whimsical decision. When picking “feast” I just thought, “This will be fun.”

Syd: Yeah. Yeah.

Tracy: Actually, I know that themed words were something that certainly weren't ruled out. So, I didn't have any rules imposed on me and I just did it. And then when it came out on Thanksgiving, I was traveling, I was with my sister in California. And I started to become aware that some people were not responding positively.

Syd: How did you find out?

Tracy: I feel like somebody told me that they were talking about it on Twitter. And I went and looked.

Syd:  Oh no.

Tracy: And I know that Twitter was just the tip of the iceberg, because there was actually a Subreddit where it was really being talked about.

Syd:  Oh wow. Yeah.

Tracy: I decided not to go and look at Reddit.

Syd: No, don't go on Reddit.

Tracy: Twitter was already bad enough.

Syd: That's enough. Yeah.

Tracy: Yeah, and the comments were like, “How do you fuck up something so simple?” 

Syd:  Oh, no.

Tracy: Or, you know, “She's gonna ruin Wordle.” And then there was a Slate article that said, “New Editor Ruining Wordle” that was the title. And so, I suffered, yeah, I was just feeling bad. I mean, how else are you gonna feel? You don't want to let anyone down. And I was also worried that maybe my employers were mad at me.

Syd: Were they?

Tracy: No, they were quite supportive and not only were they supportive, they were like, “There's nothing wrong with trying this. We were talking about themes.” But also, they said there was no noticeable blip in usage. People were so mad but usage of Wordle didn't go down.

Syd:  Mmm. Okay so, you’re fine.

Tracy: Then I tried to respond to everyone in a statement on Twitter and I said something like, “That was just a flex. I'm not like planning on doing this as a normal thing going forward.” And the guys on the Wordle With Friends podcast were like, “Outrage! More themes! Rub it in those cry babies faces!”

Syd: Ha! fantastic, that's great.

Tracy: Yeah, they were exceptionally nice. That got me out of the funk that I had been in. It felt like everything was gonna come falling down and then I was just like, “Oh this is just like some Twitter assholes.” And that even if they have a point, I think my perspective on it is that people are very passionate about the game and words matter. And I want my detractors to love and enjoy the game. I'm not gonna make a battle out of it. Just because they're going into adversarial posturing I don't need to answer that with adversarial posturing. I'm just gonna be nice and keep going.

Syd: Switching gears for a second. I really liked how much you talked about the mystical and magical perspective you have on this career path and how that seems to be something that you always pay attention to in your life. Do you think that kind of natural predisposition to be aware of the play that exists on a kind of cosmic level is what makes you especially suited to this work?

Tracy: I don't know how to answer that but I do feel it is my calling. I do feel like every time I've been on my path I've had these confirmations in the form of synchronicities. And every time I've been off my path, I've had more obstacles and things pushing me away. 

Syd: How do you see the role of puzzles in people's lives? And your role as the constructor of the puzzles? How do you think about the impact of your work?

Tracy: I feel like one of the reasons it's a real privilege to work in this job is that the whole point of games and puzzles is to bring a lightness and joy to people's lives. That they can feel like it's a problem they can solve. 

Syd:  Oh, wow. Yeah.

Tracy: It's a problem that is solvable. And puzzle makers actually don't want to defeat the solver; they want the solver to fully solve the puzzle. The puzzle makers want it to be challenging but fair, that’s a phrase I borrowed from Merle Regal's philosophy on games. But I think it's every good puzzle-makers philosophy, puzzles should be challenging, but fair because you do want them to be solved, ultimately, because that's the feeling of satisfaction that brings people back to the next puzzle.

Syd:  Yeah, right.

Tracy: And, you know, it's a relief to do a puzzle after you've read the news and solved household problems. It's a mental challenge that is satisfying to solve, and feels good.