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Episode 7: Will Nediger
391 Plays17 days ago
Daniel and constructor Will Nediger discuss topics including solving the ship of Theseus paradox, the qualities of a good crossword editor, training for the ACPT big board, tailoring for specifics venues, drawing inspiration from visual arts, inferable entries, slightly NSFW clues, craving the weird and wacky, and much, much more.
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Transcript
Introduction to 'Crosstalk'
00:00:12
Speaker
Hello, puzzle people. My name is Daniel Grinberg, and you're listening to episode number seven of Crosstalk, the crossword construction podcast. In this show, I'll be talking to other crossword constructors to learn more about how they work and what inspires them.
00:00:27
Speaker
Whether you're a current constructor, an aspiring one, or a fellow word nerd who wants to find out how a puzzle gets made, this show will be a forum to share insights and learn from each other.
Meet Will Nediger
00:00:39
Speaker
For the seventh episode of Crosstalk, I'm joined by none other than Will Nediger. Will is a professional crossword constructor based in London, Ontario. He's published 52 crosswords in the New York Times, as well as many others in the New Yorker, the Walrus, the Wall Street Journal, USA Today, and his own puzzle blog, Bewilderingly, among many other venues.
00:01:01
Speaker
He's also the crossword editor for Spyscape, an espionage-themed publication. And he won second place at the 2025 American Crossword Puzzle Tournament out of 787 competitors.
00:01:15
Speaker
Will, thanks so much for joining me today and giving us a clue about how you work. Thanks so much for having me. Absolutely. So to kick things off, I wanted to ask you what I ask everyone, which is what originally led you to begin solving crosswords?
Journey to Crossword Construction
00:01:31
Speaker
It's a hard question for me to answer because I feel like I've always been solving them ever since I was a kid because I've always been obsessed with words. But I definitely solved the crosswords that were in my local paper, which were syndicated and I think At the time, they had LA Times puzzles, they had New York Times puzzles, and they also had the Saturday Stumper, which I could not even come close to solving.
00:01:53
Speaker
And I had no idea it was one of the hardest puzzles out there until years later. So I was weaned on those and then What really got me into it was Games Magazine.
00:02:04
Speaker
So we had a cottage up in Northern Ontario and the corner store down by our cottage always stocked Games Magazine. So I would get it every time I was up there in the summer and spend hours and hours working through the puzzles there.
00:02:16
Speaker
Yeah, I was also doing a lot of Games Magazine as a kid. I'm sure there's a pretty big overlap of game solvers and crossword constructors. And then do you remember what led you to begin constructing yourself?
00:02:28
Speaker
Again, I don't remember an exact moment, but I just enjoyed it so much. I was like, you know, maybe I could do this. And I started doodling around with graph paper.
00:02:39
Speaker
Yeah, this was when I was, I don't know, maybe 10 years old or something. And I had no idea what I was doing. I didn't have a mentor or anything. I didn't even know that you could find a mentor. So I tried to figure it out on the fly and it took lots and lots of erasing and lots and lots of practice.
00:02:56
Speaker
And at what point did you switch from graph paper? It must have been... or are you still using it? No, I'm not still using it. I mean, i do hand construct sometimes still, figuratively hand construct. I'm still on the computer.
00:03:11
Speaker
But definitely before I had my first puzzles accepted, i was on the computer by then. so And that was in like 2005. So I've been on the computer constructing for at least 20 years Wow, that is a long and storied career already and you're just getting started.
00:03:27
Speaker
So along those lines, you had your first crossword published in the New York Times when you were 16 years old and then you already had six accepted by the time you were 18. How did you level up so quickly?
Evolution in Crossword Construction
00:03:39
Speaker
This is the case for everyone. You look back at your old puzzles and you're embarrassed by them, right? I'm sure you have this experience, even though your old puzzles are not as old as mine. My old puzzles are very old.
00:03:52
Speaker
And, you know, the early 2000s was a different time. Standards are so much higher now. And places like the Times and everywhere really get so many more submissions. So nowadays, I don't think of it as much of an accomplishment to get published in the Times or to get published in whatever newspaper back in 2005 or 2006 as it is now.
00:04:13
Speaker
So I don't know if I accept the premise that I really leveled up a lot by that point. One thing I think of about my old puzzles is that I really fetishize the Scrabble letters just for the sake of their rareness and Scrabble-ness. And I think that fit in with the crossword culture at the time.
00:04:27
Speaker
Editors really liked that sort of thing. And I liked that sort of thing. So it meshed together, even though from my perspective as a constructor now, I try to use those more thoughtfully as opposed to saying, well, there's a J. It must be better than something without a J, you know, i stuff like that.
00:04:44
Speaker
if Yeah, or a cue. I mean, that's the holy grail. And then who were some of the people you were inspired by in those early days? A lot of the big names from that period, I mean, definitely Brendan Emmett Quigley, definitely Elizabeth Gorski.
00:04:58
Speaker
I was also really inspired by Frank Longo because i I did a book of his themelesses, like super wide open themelesses around that time. And i learned a lot of entries from there. Again, this was when I was a kid and I didn't really know anything. So like I found these puzzles very difficult, but I plowed through them. I looked up stuff in the back a lot and I learned a lot of A, the standard crossword entries and lots of long stuff.
00:05:20
Speaker
that I haven't even seen since, but that might make a comeback. But I was just amazed by his ability to put together these really, really wide open grids. Yeah. And then I was looking through some old interviews you did.
00:05:33
Speaker
And in 2010, you said when you started out, you were, quote, in the habit of putting in entries that seemed like they might be words and then hoping that they would turn out to be in the dictionary.
00:05:45
Speaker
And I'm guessing slash hoping that you don't do that anymore. Could you maybe tell us what are some of the other notable ways your process has changed since you were starting out? Since I was constructing on of graph paper, I didn't have a word list. I mean, I had a lot of dictionaries in my house. Like I was a big dictionary guy.
00:06:02
Speaker
So I could look things up. But I was sort of like, okay, this seems like a word. Like I remember I was making a crossword for like a family friend. And I kind of backed myself into a corner. And I put mitsu in there. And I'm like, well, that's half of the word mitsubishi.
00:06:14
Speaker
It probably means something in Japanese, but I don't actually know. You know, that's the kind of thing I was doing at the time. Now, of course, I don't do that anymore. The process per se hasn't really changed that much aside from the fact that now I use real words all the time.
00:06:29
Speaker
It just involves a lot more iteration, way more iteration than it used to. Yeah. And you... Along the way, got a PhD in linguistics, which with everything you've been saying about the dictionaries and the obsession with words makes
Linguistics and Crosswords
00:06:45
Speaker
a lot of sense. And it also seems like would be a pretty useful background for a constructor.
00:06:50
Speaker
Can you talk a little bit about how that training and that disciplinary background has informed your development as a constructor? There's a lot of stuff that usually unwritten, although occasionally written, I mean, these things get written up in in books like Patrick Berry's handbook and stuff, but the basic rules of how clues work are often hard for beginning constructors to get their heads around because when you're solving the puzzle, there's no explanation of them, right? There's this whole language that you're sort of, as a solver, just expected to to be able to understand. So things like the clue and answer have to match in part of speech. They have to match in number. So whether it's singular or plural,
00:07:25
Speaker
They have to match in transitivity, whether they take a direct object or not. All these things and things like substitutability are, I think, just a little easier to grasp if you have the linguistic background of understanding what the formal linguistics concepts behind these rules are.
00:07:41
Speaker
So I found that to help a lot. I've thought before in a parallel dimension, linguistics very well could have been the path I ended up on. So I do appreciate you sharing that. And then turning to constructing when you're starting on a new puzzle, how do you get that initial process going?
00:07:58
Speaker
It varies a lot depending on what kind of crossword I'm making. If it's a theme crossword, say, i really enjoy the theme brainstorming part of the process.
00:08:10
Speaker
So if I've got a theme, i will spend half an hour, an hour or whatever, searching through my word list, finding things that are going to fit the theme, and then trying to curate which theme entries, A, are going to work symmetrically,
00:08:25
Speaker
or asymmetrically if it's a venue that doesn't need symmetry, and then really trying to whittle them down to the best set and thinking about what order they should go in in the grid. I think that's something that's really important. Often you'll save the best one for less, so it's sort of like a punchline on the theme, but there's a lot more to figuring out what order, I think.
00:08:46
Speaker
Sometimes you want theme entries that use different approaches to be alternating with each other or something. So you're not starting out with two theme entries that work the exact same way and then throwing this over over for a loop with one that's slightly different.
00:09:00
Speaker
So if you've got one that's slightly different as the second theme entry, and then for the third one, you go back to one that's the same as the first one, Then the solver gets into this sort of mindset, okay, they're alternating. They're not shocked by the fact that suddenly you're changing things up on them halfway through the puzzle. So I like to think about that kind of thing a lot before I even start to put anything in the grid and start filling.
00:09:22
Speaker
Yeah, it is interesting you say you sometimes save your best for last. I feel like I try to put my best one first to try to get the solver to buy in. I feel like by the end, if you put it at the end, they might just have given up at that point.
00:09:37
Speaker
Yeah, that's true, especially on like a Sunday or something, because a Sunday is the kind of thing that solvers might give up on if they're not grabbed by it. Because they're like, if I'm not enjoying this, why am I going to spend 45 minutes more on it?
00:09:52
Speaker
Yeah, or ideally, all of your entries are the best and they're all tied for first place. That would be perfect. I wish we lived in a world like that. think it was a recent times puzzle that involved switching the first two letters of words in an entry to make wacky phrases.
00:10:10
Speaker
Then the last entry changed the phrase nuclear option to unclear potion. So this change of switching the first two was happening not in just one word in the phrase, but it was happening in both words.
00:10:22
Speaker
And that one was last. And I sort of liked that it was last because it was like, oh, hey, we're doing even more this time. Whereas it would be anticlimactic if you put that one first or put that one in the middle. And then it's kind of like downhill from there, right?
00:10:34
Speaker
Yeah. You're talking about Trenton Charleston's Sunday Times puzzle from November 23rd, 2025. And that puzzle was really good at training you to handle the theme even better by the end.
00:10:48
Speaker
And on the topic of themes, I do have to say your themes immediately come to mind as standouts. I think I associate you with excellent themes partly because they can seem straightforward and intuitive, but somehow they eluded me.
00:11:07
Speaker
Like your recent echolocation themed puzzle in the New Yorker from November 24th, 2025. I was like, it was right there all along. Why did I not think of this?
00:11:19
Speaker
And i think that a lot when it comes to your puzzles. That's so kind of you to say. It's funny you give that particular example because that when the editors of The New Yorker reached out to me because this was for a special issue. They have themed issues for their 100th anniversary.
00:11:34
Speaker
And the theme of the issue that they wanted a puzzle for was our far-flung correspondence. So they wanted something related to like exploration or travel, travel journalism. I spent so long, I spent a ridiculous amount of time brainstorming themes. And like I sent two or three themes to them that they didn't like before I came up with this one that they did like.
00:11:54
Speaker
So it was really not just the kind of theme that comes to you, or at least it's not the kind that came to me. It took me hours and hours of thinking. That brings up an interesting point that sometimes having a constraint of a particular issue or particular venue that specializes in something can help inspire you to think in in very specific ways. Whereas if you have complete carte blanche, you can feel a little more adrift because you can really take it in any direction.
00:12:21
Speaker
Yeah. So while we're talking about themes, maybe you could extrapolate a little bit about where your theme ideas come from or how you start generating ideas.
Creating Themes and Inspirations
00:12:32
Speaker
They come from everywhere, basically. I think like most constructors, I just try to keep an ear and an eye open for phrases that might be revealers or concepts or things out there in the world that could be visually represented in a bunch of intersecting black and white squares.
00:12:50
Speaker
For me, what I usually do is if I have a seed of an idea, then I write it down in a giant disorganized text file that I have, which is titled Stuff, and it has like a bunch of stuff in it, including... all my theme ideas and mini theme ideas and theme list seeds.
00:13:06
Speaker
And usually i don't do anything with it immediately. I have it in my list and partly that's because I have other deadlines or whatever to work on.
00:13:17
Speaker
And I come up with a cool theme and I'm like, well, I have to finish these 10 other things before I can even think about this theme. But the nice thing about that is it lets it percolate. So I can think of what the exact best way to like use this idea is.
00:13:31
Speaker
And it's nice that we live in a time where there are lots of different venues that do different kinds of approaches to themes. So that whatever kind of half-baked seed idea I have, there's a chance I'll be able to turn it into something.
00:13:43
Speaker
It might be that I turn it into a standard newspaper puzzle that I submit. It might be the case that I can only come up with two theme answers that fit the theme after brainstorming for a while.
00:13:55
Speaker
So I'm going to use it for a MIDI instead, right? Like and I'll send it to Puzmo or I'll use it in Vox if it fits in a 9x9 grid. It might be the case that I have this cool wordplay observation and I can't find any other entries. that have the same wordplay property. And in that case, use it as a cryptic clue or something like that, right?
00:14:13
Speaker
Maybe it's it's the kind of theme that only works with an asymmetrical set. So we'll send it to Apple News or somewhere else that doesn't require symmetry. There's just so many options now. I generally find that any idea that I have is going to be able to turn into something, whether it's just a single clue somewhere or it's like a full-blown Sunday-sized theme.
00:14:31
Speaker
Yeah. And one of the things you're identifying there is knowing the venues and what they specialize in or what sets them apart can be a really powerful way of making sure the right idea is going to the right publication.
00:14:45
Speaker
Absolutely. I think that's really important if you're submitting to somewhere to think, is this the the best place to submit this puzzle? Am I submitting it just because I had this idea that I love and I want it to be published somewhere?
00:14:59
Speaker
Or does it really fit at this venue? Exactly. So while we're talking about themes, I wanted to talk about some specific themes of yours that have stood out to me. One that I remember pretty vividly is Sea Change, which came out May 7th, 2023.
00:15:16
Speaker
And spoiler alert, that puzzle literalized the Ship of Theseus paradox. And it started with Ship of Theseus at the beginning, and then it ended with the same entry, Ship of Theseus at the end.
00:15:28
Speaker
Can you tell us a little bit about how that idea came to you? Yeah, I like to read a lot of philosophy, so I was probably reading something that mentioned the ship of Theseus. So for any listeners who might not know, imagine you've got a ship and you replace the boards of the ship, this wooden ship, one by one with new boards. but Eventually, there's no original boards remaining.
00:15:49
Speaker
And the question is, is it the same ship as before or is it a different ship? It has completely new materials, but you've never at any single point completely changed it. You've always changed it one board at a time.
00:16:01
Speaker
So there's always been this continuity there. And something about that idea just reminded me of a word ladder. Like you're changing one thing at a time and you end up with a word that's completely different in a standard word ladder. Like you might be going from love to hate or something like that, or or hate to love, I suppose, is more optimistic.
00:16:17
Speaker
ah And I was tickled by the idea of having a word ladder where you start with the one word. and end up changing everything but then circling back to get to the same word in the end. And it's like, is it really the same word or is it different now?
00:16:32
Speaker
So let me ask you that question then. Do you think that the ship is different at the end or the same? ah You're putting me on the spot here. Yes, i am. I'm a Wittgenstein guy. a lot of philosophical puzzles are basically language puzzles. They're like language games. And I don't know that it says something meaningful about the concept of identity as an abstract concept to say, oh, it's the same ship or it's a different ship.
00:16:58
Speaker
You can use the word same in either way. That's just part of the polyvalence of how we might use the word the same. And so this is kind of a cop-out answer, but... I don't think there's a correct answer. I think it's just a linguistic artifact.
00:17:11
Speaker
Maybe it's the shipmaker that changes along the way and not the ship. The real ship was the friends we made along the way. The real ship was friendship.
00:17:21
Speaker
I think we figured it out. All right. And then about that puzzle, you wrote, I love dupes, and I especially love dupes that make you question whether they even count as dupes, which fits nicely with what you were just saying.
00:17:36
Speaker
So could you tell us a little bit more about what draws you to breaking the rules in your constructions? Yeah, there's a quote that I really like from the Chilean poet, Nicanor Parra. It goes something like, in poetry, everything is permitted with the one condition that you have to improve on the blank page.
00:17:54
Speaker
And I feel the same way about the crossword rules. It used to be the case that a lot of rules were sort of taken as dogma.
Breaking Rules and Personalization
00:18:01
Speaker
The theme entries have to be placed symmetrically. And there's a couple different motivations for that. One is just pragmatic.
00:18:09
Speaker
The solver is going to more easily be able to identify which ones are the actual theme answers, if they're placed symmetrically and if they're the longest across entries in the puzzle. So this is a practical reason and it makes a lot of sense.
00:18:22
Speaker
But that doesn't apply to every theme, right? I mean, there's some themes where it's very clear which ones are the theme entries just from the clues. Like they might all be clued the same way. They may even have stars on the clues and stuff. And the other justification that people give for saying that things have to be symmetrical placed and grids have to be symmetrical is aesthetic. It looks nicer, right?
00:18:41
Speaker
And that's true. You know, symmetry looks nice. There's just something appealing about a symmetrical grid. But it's it's not the only way for things to look nice. It's not the only way for a grid to be aesthetically appealing.
00:18:52
Speaker
So I'm very happy about the fact that there are venues now, more and more, that are allowing the the symmetry rule to be broken. And, you know, so Universal just very recently dropped their symmetry requirement.
00:19:06
Speaker
I mentioned Apple News doesn't require symmetry. USA Today doesn't require symmetry. And I think, in general, the editors of those venues... have a good eye for when an asymmetrical grid is aesthetically pleasing and when it works for the solver. So I'm very happy to see that kind of development.
00:19:26
Speaker
It's interesting you bring up aesthetically pleasing as a criterion of acceptability. Going along with your rule breaking, it's making me wonder if there could be fun ways of intentionally playing with ugliness and imperfection that could add thematic resonance.
00:19:45
Speaker
I'm sure there have to be some good examples of that out there. Yeah, totally. And another theme of yours that I loved was from your May 26, 2021 Times puzzle.
00:19:56
Speaker
You had the revealer See Me After Class, which had school classes that were followed by words starting with M-E, like German measles or gym membership.
00:20:07
Speaker
And I really like themes that take common phrases like that and reframe how we parse them. We just had a really good recent one in the Times from Kareem Ayas with under repair becoming the letter pair R-E-R-E.
00:20:24
Speaker
And both yours and Kareem's have now rewired how my brain interprets those phrases. So could you tell us a little bit about that puzzle and how it came about?
00:20:35
Speaker
and In this specific case, i I don't think I encountered this phrase in the wild because, you know, I haven't been told see me after class in years, you know. but So I'm not encountering this phrase in everyday life. But see me is a very common entry in crosswords. And see me after class is occasional because it's 15.
00:20:52
Speaker
So I'm pretty sure I saw this in a crossword and I was like, oh, yeah, this could be reparsed. And yeah, I i love the kind of theme that makes you see a revealer differently. And i think Kareem is great at that kind of thing. He's so good at Kamehaka themes. And that was one of my favorites of his.
00:21:07
Speaker
He is definitely great at that. And then I noticed also on your website, you talk about making custom crosswords for events like birthdays, anniversaries, Christmas presents. Could you tell us a little bit about how those kinds of ideas come to you and what some of the most memorable constructions have been from those kinds of projects?
00:21:28
Speaker
The custom crosswords are some of my favorites to make because they're for an audience of one. And so you don't have to have this whole complicated calculus about, is this going to land with the solvers? Like how many solvers are going to live this? How many solvers are not going to know this? How many solvers are going to hate this, right?
00:21:45
Speaker
There's only one solver that matters. It's whoever the crossword is for. And so you can get really specific. I just did one where it was for this person's husband, who's a big fan of P.G. Woodhouse's books. And so she just wanted a ton of characters from P.G. Woodhouse in them, which is great. When I was a teenager, I devoured his novels. So I was like, this is perfect.
00:22:04
Speaker
There was one where the recipient was a climate policy person. And again, I think it was their wife who was commissioning it. And she was like, yeah, I want you to go all in on the climate stuff. The revealer was rising sea levels.
00:22:21
Speaker
And there were phrases with c near the bottom of the grid where that C had been removed to make a wacky phrase. And then at the top of the grid, phrase is where you had added the C to make a wacky phrase. So as if the letter C was going upwards in the grid.
00:22:35
Speaker
And then the second revealer was carbon emissions, I think. So it was like, again, C for carbon being emitted by some of the entries. And this is the kind of theme that I think works very nicely from a wordplay perspective.
00:22:47
Speaker
It's got that double revealer. And both of the revealers are very topical, but it's the kind of thing I would never submit because the topic is such a bummer. Like, I'm not going to submit this to a newspaper or whatever. Like, no one really wants a puzzle about rising sea levels, I assume.
00:23:02
Speaker
I want one. Well, the point is, I guess some people want one, like the recipient of this puzzle definitely wanted one. But there's a lot of people I think who would be bummed out by it. You know, they get enough news about climate related disasters that they don't need it in the puzzle.
00:23:17
Speaker
But the great thing about a custom puzzle is that I didn't have to worry about that. You know, I asked the person who was commissioning it whether it would be too much of a bummer. And she was like, oh no, he deals with his bummer stuff all the time. He would love it.
00:23:28
Speaker
We could definitely theorize and philosophize about what constitutes a bummer, but I'll leave that aside for now. So when you have your theme entries all figured out and you're ready to start grading and filling the grid, what is your process
Crossword Strategy and Collaboration
00:23:43
Speaker
for doing that?
00:23:43
Speaker
Trying to give myself as much of an advantage early on as possible, which means setting up the black squares in a way that make it easier for future me to fill the puzzle. And starting in the areas that are hardest. So again, future me has an easier job.
00:24:00
Speaker
So yeah, setting yourself up for success, basically with the black square placement. And of course, you can't always predict everything. Sometimes you get a black square arrangement that seems really great. It seems like there are lots of possibilities that are going to be there. And then for whatever reason, it just doesn't work. So you go back to the drawing board. Yeah.
00:24:18
Speaker
And what about your process for cluing? Cluing is, my process is so over the place because I find sometimes I'm just in the zone with cluing and sometimes I'm just absolutely not.
00:24:30
Speaker
I write so many puzzles. I write a ton of puzzles. And so I end up having to clue the same entries, any like decent short entry. I've clued many, many times. Of course, all the crossword easy stuff.
00:24:43
Speaker
And so I find myself defaulting to a very narrow set of clues that I've seen and used a bunch. Like if I'm cluing era or whatever, the first thing that pops into my brain is always timeline slice.
00:24:55
Speaker
And some days it's easier for me to get out of that rut kind of headspace. And some days I can't. And so I have to set it aside and come back when I'm better headspace take a shower or something.
00:25:07
Speaker
So it's it's all over the place. Yeah, the shower is a powerful place to let your unconscious mind do some work. I'll often give it a try if everything else is failing.
00:25:18
Speaker
And even if it doesn't work, at least you got clean. And then do you have a particular way of working, like a certain location or a particular time of day, for instance? It's my day job, so I'm working basically all day on it in my office in the basement of my house. I'm also like a creature of habit very much. I thrive on routine, so I'm always sort of in the same space, working from the same time in the morning to the same time in the afternoon.
00:25:46
Speaker
It's interesting because I'm sure a lot of constructors would love to do this as a full-time job, but I'm sure it also comes with its disadvantages or its sacrifices. Do you treat it like a nine-to-five job then?
00:26:00
Speaker
I do treat it as a nine-to-five. i used to do it all the time. like I would work on a puzzle nine in the evening or whatever if I had one that was really excited about. And I have sort of a bad habit. I can just work all day on something if it's a crossword because I'm so passionate about it and I can burn myself out that way.
00:26:16
Speaker
Mostly I don't do that anymore because I have kids. And so when I'm not in my nine to five time, then I'm mostly taking care of the kids. And then when they're asleep, I'm tired enough that I don't want to make a puzzle.
00:26:29
Speaker
right So that has forced me to have a better relationship with the work, I think. Yeah. I have noticed sometimes when I really get in the zone and I'm just fully focused on crossword mode, I will be sitting in my living room working on it and I won't even notice that it's gotten dark and that the room is completely dark because I'm so focused on my screen. And then I'll look up and I'm like, oh, it's nighttime. And I did not even know that happened. So yeah, I hear you on that.
00:26:57
Speaker
And then I've noticed you've also collaborated with many constructors along the way. Could you tell us a little bit about how your process shifts when you're collaborating? The thing I love about collaborating is that it slows me down. When I'm working on a puzzle that's just my own, sometimes I just am very excited about the theme or whatever, and I want the puzzle to be a complete object as soon as possible. And of course, when you're collaborating, you have to, however you're doing it, usually I'm doing back and forth over email or Discord. So there's built-in breaks in there that let the puzzle simmer a little bit.
00:27:34
Speaker
So that if there's any ideas or possibilities that I missed while I was doing one particular session of greeting or theme brainstorming or whatever, there's a chance for those to come to the fore. And of course, there's a chance for your collaborator to come up with something that you yourself never would have thought of, which happens pretty much every time I've done a collaboration.
00:27:54
Speaker
Yeah, I feel like I'm maybe not the ideal collaborator because they will probably be busy with other things. And I will, like you said, get really excited and get really eager. And I'll just be like, oh, I you know i made like 15 iterations here. They all are. I couldn't wait.
00:28:10
Speaker
They're like, oh, okay. that's That's a lot, but thank you. So yeah, sometimes it's hard when the rhythms don't quite match up. And then what kinds of tools or software do you use now?
00:28:23
Speaker
I've always used compiler. And so I still use it largely out of habit, but I also really like it. works really well for my purposes. And I've also tried out Crosserville and Ingrid, but of curiosity, and I like both of them. As many people have said on this podcast, Ingrid is a thing of wonder. Like it's a really great piece of software. And I haven't switched over it to it because I'm so used to compiler now. I've been using it for decades.
00:28:51
Speaker
And then outside of the constructing software, what kinds of resources or tools are you using? So many online ones. I use onelook.com a lot. I use it multiple times a day, I'm sure.
00:29:03
Speaker
i use Word Listed, Adam Aronson's website for coming up with themes. Many of the resources that Alex Boivere has put up. Alex Boivere is my hero because there's just so many things he's put up completely for free to help constructors.
00:29:19
Speaker
You know, he's got the online solver. He's got these applets for generating variety puzzle formats, like the grids for those that you can't make easily in the standard software.
00:29:30
Speaker
And then he has more recently one that I really like, which is a clone of Kot, Q-A-T, which is a website that lets you, it's kind of like regex, but more so like it lets you type in a pattern and find words with that pattern and then words that have a similar pattern but slightly different. so you can find pairs of words that relate in certain ways, which is really, really good for coming up with themes.
00:29:52
Speaker
I always feel like I might know all of the tools at this point, but then I talk to others like you and I realize there's still way more to learn. So I'm going to have to check that out. I appreciate you sharing that.
00:30:04
Speaker
And we've talked a lot about theme process now, but you also construct themelesses. So could you also tell us a little bit about your process for those? Yeah, these days I usually start with a clue entry pair.
00:30:17
Speaker
Like I usually am not starting with a seed entry just because I like the entry itself, but because I have a wordplay clue for it, or it doesn't have to be wordplay clue, just a clue that i really like. And probably that's because I don't trust myself to be able to come up with these wordplay clues once I've got a grid and I'm like, now I have to clue it. So if I happen to think of a nice seed clue, I'm like, well...
00:30:40
Speaker
This is how I'm going to start the puzzle, because otherwise I might end up with a great grid with lots of cool entries that seem like they could be nicely clued. And then when it comes to cluing, I just have a devil of a time actually coming up with good clues.
00:30:52
Speaker
And so it just gives me this reassurance that at least there's going to be one Cracker Jack clue in the final puzzle. Oh, that's kind of amazing to me that you've been doing this for 20 years and you're still not fully trusting yourself to come up with great clues.
00:31:07
Speaker
ah Well, part of it is that it's really hard after 20 years to not repeat yourself or to repeat other constructors, right? Like there's lots of great clues that have been used before.
00:31:18
Speaker
So hard to come up with a wordplay clue especially that's really good and also original. I'm just in awe of the constructors who do that on the regular, like Eric Eggard has a seemingly impossible ability to do that, but I'm not one of those people.
00:31:33
Speaker
So I like to start with a seed. So i have a seed list of specifically of wordplay clues that I want to use. And then these days I'm often stealing people's grid patterns because I have so much choice paralysis.
00:31:45
Speaker
I will often solve an Aiden Nicole puzzle from her Patreon and be like, okay, this is cool. It has a stack of 13, then 15, then 13 in the middle. And I haven't done something like that recently. So I can use my 13 letter C that way. And I'll build up from there.
00:32:01
Speaker
So you mentioned that you've been doing this a long time and you're trying not to repeat yourself. Do you still feel inspired and energized? How does that work?
00:32:11
Speaker
Yeah, absolutely. I don't feel like I've been burned out. And that, of course, is always the risk of turning your passion into your day job. But I think I have the right kind of personality to do it. And I really think, yeah, there are certain personalities that really work well. with having your passion as your day job. And it helps to think, well, I could have a different job that's not that, but it would probably suck because it wouldn't be making crosswords. i Like most jobs suck, right?
00:32:38
Speaker
And this one doesn't. So it helps me feel grateful, which helps not be burned out by it. Yeah, I'm really happy to hear that. And in addition to being such a prolific constructor, you also do a lot of editorial work. As I mentioned earlier, you're the crossword editor for Spyscape. And with Brooke Husic, you've also co-edited 99 TV crosswords for a twenty four And you've also edited some puzzles for Science News.
00:33:06
Speaker
What do you think are the qualities of a good crossword editor? One important thing is being able to toggle between looking at things on the small scale, like looking at individual clues and figuring out whether this clue works, how can the wording be improved, and then toggling between that and the big picture, like the gestalt of the puzzle and the gestalt of the section that that entry is in.
00:33:31
Speaker
So like a clue might work perfectly in a vacuum, but it's too hard for this particular section. Like this section has enough hard stuff in it, so it needs to be eased up. Or there's too many proper names in this section, so you shouldn't clue mill as like a surname.
00:33:46
Speaker
I think that's really important as an editor because often as a constructor, you kind of take every clue individually. and it's very hard to juggle all of the different considerations when you're in the throes of writing the puzzle itself.
00:34:02
Speaker
How do you manage to ensure you don't put too much of your personal taste or your own preferences into the editorial decisions? If anything, i have the opposite problem.
00:34:14
Speaker
I might put too little of my personal preferences because I'm the type of person who will not advocate for myself just as a general personality trait. do I tend to err on the side of preserving what the constructor has sent me, which is great in one way. It's great to preserve the constructor's voice and the choices that they make when those choices work for the puzzle and are going to work for the solver.
00:34:39
Speaker
And so the challenge for me is more knowing when to change something. Yeah, that is an interesting dilemma. And relatedly, i mentioned that you're the editor for Spyscape, where the focus is espionage themed puzzles.
00:34:55
Speaker
I just had a few puzzles published there recently, which I was very excited about. But I've wondered with a topic as specialized as espionage, do you ever feel like, okay, we've now published every possible angle there is? How do you edit something so specialized in terms of keeping it fresh?
00:35:16
Speaker
Yeah, I do worry about that. If I was just writing it myself, I would have given up years ago, I think, just trying to come up with new themes. I'm very lucky to have a lot of regular constructors who submit there all the time, who, A, tend not to repeat a lot of things because, you know, they're regulars and they solve the puzzle so they see what has been done.
00:35:35
Speaker
And they know what I'm looking for. and I particularly want to shout out Bryant White. About half of our puzzles are written by him. He's a spy media buff. And he comes up with these very original themes that are not a standard wordplay revealer based theme, but they have a narrative to them. You know, the spy club is having a party, but somebody has pulled a prank and you have to figure out who pulled the prank based on like some hidden words in the grid.
00:35:59
Speaker
Yeah, Bryant's puzzles are definitely a highlight. And in your experience as an editor, do you have insights on how constructors can stand out among the dozens, if not hundreds of competing submissions?
The Art of Polishing Puzzles
00:36:14
Speaker
I would say the main thing is to just polish, polish, polish, really. It's almost always the case that your first or second or third iteration of the fill can be improved upon.
00:36:26
Speaker
And so if you can come up with a fill that's incredibly polished, everything is clean, there are no entries that an editor is going to possibly look askance at.
00:36:37
Speaker
you're setting yourself up for success, especially because it's impossible to predict the preferences of individual editors and venues. That makes sense. And then taking off your editor's hat and putting on your solver's hat, some people may also know you for your very impressive finishes at the ACPT, the American Crossword Puzzle Tournament. You came in third place in 2024 and second place in 2025. So I think we know what place is next. Yeah. How do you prepare for all the tournaments that you do?
00:37:08
Speaker
Well, from your lips to God's ears about that prediction. The main thing is just solving a ton of puzzles, but ways to specifically prepare for competitions. I do solve a lot of puzzles down only these days because when you're solving on paper,
00:37:24
Speaker
which you do at the ACPT and at most competitions, a lot of the time spent is finding the clue. And if you can largely do a puzzle, especially an easy puzzle, by running through the downs and not having to switch to look at the crosses a lot, it saves a ton of time.
00:37:41
Speaker
So being able to do that and rely on looking at the letter patterns that you have and figuring out what the only possibilities are without actually looking at the across clues is a big boon. That seems harder than you're making it sound, but good to know.
00:37:56
Speaker
And what is it like solving a puzzle on stage with a whole audience watching you? Solving a puzzle on the big boards is weird. Although for me, it's not primarily weird because of the audience. Because when you're solving the puzzle, you kind of forget about the audience, or at least I do. I mean, you've got this white noise being piped into your...
00:38:15
Speaker
headphones and you're facing away from the audience, it's easy to just totally forget that they're there until you hear them loudly cheering for Paolo or whatever. um It's easy to forget, but I find the experience extremely weird because...
00:38:31
Speaker
The board is giant. You cannot see the whole thing at once in the way that you can when you're solving it on just a regular piece of paper. And I really rely on being able to see the whole thing at once and like seeing what the letter patterns are, which helps me know where to go next based on what letters I have, like what's going to be easiest.
00:38:47
Speaker
And it helps me, you know, be able to fill in entries without looking at the clues just by seeing what letters are in there. And it's very hard to do that when you're solving on the big boards and your eyes are looking between the paper with the clues on it and this giant whiteboard in front of you. So that for me is the weirdest part of it.
00:39:02
Speaker
Yeah. Luckily, I'm probably not going to have to worry about that anytime soon. And then I wanted to talk a bit about life outside of puzzles. So I started out last episode by asking Amy for a fun fact. So I also wanted to ask you if you could share a fun fact about yourself that fans of your work might be surprised to learn.
00:39:22
Speaker
Well, unlike Amy, I do not know any of the Obamas. Oh, no. So my fact is, it's not going to be that fun. Do you know the Trudeaus?
00:39:32
Speaker
No. i mean, the closest relationship I have to the Trudeau's is that my wife ran into them at the Toronto Aquarium once. There you go I think that's too much of a separation to be a fun fact about me.
00:39:44
Speaker
One thing about me is that i love walking. I'm a walking fiend, and I don't do it much anymore because I have to drive places, which makes me very sad because I don't like cars. But i will walk for hours on end. I just love it. And tying back to crosswords, it's very good for getting the creative juices flowing. I could do it all day.
00:40:01
Speaker
Are you listening to music while you're walking? Sometimes I'll do a podcast. Probably crosstalk, I'm guessing. Oh, yeah. And then what are you up to when you're not constructing, editing, training for tournaments or walking?
00:40:16
Speaker
Mostly I'm taking care of the kids, hanging out with them. When I'm not doing that or doing crossword stuff, I love to read and I don't have the time to read as much as I'd like to. and I love films. So I'm always watching films.
00:40:30
Speaker
Well, that ties in very nicely with my next question, which is, what's one piece of media you would recommend to people? This is a tough question because if I think about what are my favorite life-changingly great pieces of media, it's hard to pick one of those. And so instead of trying to pick one of those, I'm going to pick one that I think is something that crossword people might like and is something that is a recommendation that says something about what I like.
00:40:58
Speaker
And that's an album from the 70s called Q Roan. It's spelled K-E-W, like Q Gardens, and then R-H-O-N-E, like the river. It's by a few different musicians. And it's basically a concept album that has a whole bunch of wordplay in it. There's anagrams. There is palindromes. There's there's all sorts of playful word-related weirdness in it. And it has liner notes that really, liner illustrations that have to be consulted to understand the album fully and stuff like that. I think it's cool. I think it's the kind of thing that crossword people might be into.
00:41:32
Speaker
And if you want to know what my taste in media is like, you could do worse than to check that album out. I've never heard of it. So that is very interesting to me personally. I will definitely check this out.
00:41:44
Speaker
I just wanted to throw in another recommendation that you made me think of, which is the novel Anagrams by Laurie Moore, which is one of my favorite books and very much focuses on wordplay as well. It's ostensibly a novel, but it's also kind of a series of short stories where the same characters take on different permutations in each chapter and you see the different ways that they interact with each other based on these changes to their characters.
00:42:16
Speaker
So in a way they kind of become anagrams, but then it also plays with words more literally. So there you go. Two pieces of media that listeners can check out. And since we're on the subject of recommendations, that's a good opportunity to also talk about favorites.
00:42:33
Speaker
So to start out, what is your favorite part of the construction process? I mean, I'm afraid i am I'm not going to break the streak. but I just love gridding so much. I'm obsessed with gridding. Although I will say that I mentioned that sometimes I'm in the zone with cluing. When I'm in the zone with cluing, it's my favorite part.
00:42:51
Speaker
Okay. What aspect of gridding just appeals to you the most? It's like solving a puzzle in itself. There is no single solution, obviously, but it's very satisfying when you get a fill that you really love that has some cool words, some cool letter patterns, that's really clean.
00:43:07
Speaker
Just a really great sense of accomplishment when you can do that. Absolutely. And then per the times difficulty levels, is there a favorite day of the week that you like constructing for?
00:43:19
Speaker
I love... A Thursday because I love a weird theme. And I love a Monday because love the challenge of only being able to use very easy fill.
00:43:30
Speaker
I just find that kind of challenge very satisfying. So Monday and Thursday are my jams. Interesting. I don't know that I would have guessed Monday for you. And you have decades of experience, so this might be tough. But do you have a favorite puzzle or some favorite puzzles among all the ones you've made?
00:43:48
Speaker
Yeah, I've made so many that it is tough. Although, as I said, i hate most of the old ones, so that does narrow it down a lot. And some of the new ones too, but that's how it goes.
00:44:01
Speaker
One favorite that is from couple years ago, i think, is called Word Cloud. And you'll have to bear with me because it requires a bit of explanation. There's an artist named Lenore Taney, and she's a fiber artist.
00:44:15
Speaker
And one of her series is called Clouds, and it consists of grids, which is, of course, what attracted me to the idea of turning it into a crossword somehow.
00:44:25
Speaker
But the grids are not static, so what she does is she has a square grid that's suspended from the ceiling, and then she hangs strings of fiber down. from regular locations in the grid. So you've got a grid of fibers that are you know hanging down freely. So in a sense, it's a grid like a crossword grid. It's static, right? But in a sense, it's not static because you can physically walk through it or whatever and move the strings so that they're moving around and they're not exactly orthogonal anymore.
00:44:53
Speaker
And I was really drawn by that work because it combines this idea of this motif of the grid, which is very common in 20th century art with people like Piet Mondrian and Agnes Martin. But in those works, the grid is you know usually fundamentally static. And what Lenore Taney did was take that grid and make it movable.
00:45:14
Speaker
And so I made a crossword that basically did the same thing. So it was really two crosswords that were back to back on a piece of paper. And so you solve both grids.
00:45:25
Speaker
And if you cut out the columns of the crossword and dangle them, so that they can be turned around and you can see either the front grid or the back grid, then you could see instructions in sort of a meta puzzle way that would tell you which columns should be faced forward and which columns should be faced backward.
00:45:45
Speaker
And if you did that, then the bottom row of the puzzle would spell out the name of the song, Both Sides Now by Joni Mitchell. oh my gosh which is a song about looking at clouds from both sides. I really was happy with that thematic connection to have the meta answer be something about looking at clouds from both sides.
00:46:02
Speaker
And then the actual theme of the puzzle, on one side of the puzzle, or one puzzle, I guess, you had a word with rain in it and you had a word with water in it. So you had rain, water in the grid. And then on the flip side, you had those rain and water letters in the same position, but now backwards because it was flipped. So you had...
00:46:20
Speaker
N-I-A-R, so rain backwards, hidden in Virginia real. And then you had water backwards, R-E-T-A-W, which was hidden in Lenore Taney, the name of the artist. And I loved that she happens to have the word water hidden backwards in her name.
00:46:34
Speaker
That sounds amazing. Where is this puzzle? This was on my blog. Got it. Well, I definitely need to go find this. And i imagine after hearing that, a lot of people will feel the same way.
00:46:46
Speaker
I am impressed with how you take inspiration from so many domains and disciplines. We've already touched on philosophy and climate science. Now we can add visual art and music.
00:46:59
Speaker
So it is cool how you're bringing all of these realms of knowledge and creativity to puzzles. I just am sort of an omnivorous consumer of visual and and audio and literary arts, and I try to take inspiration wherever I can.
00:47:13
Speaker
It makes for a richer set of inspirations when you can draw from so many different fields. And then what about some favorite clues that you've written? The one that I usually cite when asked this is the clue 10 Downing Street.
00:47:28
Speaker
And the answer is Peek-A-Bow because there's a skier named Peek-A-Bow Street. And for the clue to work, this had to have been in ah in a grid where 10 down was the word ski. I think that's my favorite clue, although it only works in the context of that particular grid.
00:47:43
Speaker
Another clue, slightly ah not safe for work, that I'm very happy with is they're ribbed for your pleasure. For the answer, roasties, like people who are honored at a roast.
00:47:55
Speaker
And partly why I like that is because roasties is kind of a weird entry. I don't know even know if I added it to my word list, because I feel like if I did... It would just be suggested every time I had an eight stack at the bottom of a grid.
00:48:09
Speaker
And it would feel like it wasn't there deliberately. And so I liked the fact that having it with that clue would make it feel to the solver like, oh yeah, it's in there deliberately, right?
00:48:21
Speaker
And what about favorite entries? Recently, I find myself really drawn to entries which are not super familiar in and of themselves, but which are colorful and inferable and interesting, even if you haven't heard of them before.
00:48:37
Speaker
And I often will seed my crossword club puzzles with those. So, for example, one of my favorites is the entry Billy Possum, which is, do you know what Billy Possum is?
00:48:47
Speaker
I do not, no. Most people don't, and you would have no particular reason to. But William Howard Taft tried to capitalize on the popularity of the teddy bear named in honor of Teddy Roosevelt. No!
00:49:00
Speaker
with his own stuffed animal, Billy Possum. So again, most solvers will not have heard of Billy Possum, but I think it's an interesting and and funny sort of like historical curio. And it's very inferable, right? It's named after his first name. It's an animal.
00:49:15
Speaker
And I think it's just fun. And another similar one along those lines that I used in Crossword Club was suffragic, which is the martial arts training that women's suffrage advocates in the early 20th century did to prepare themselves for hand to hand combat in case it came to that.
00:49:32
Speaker
Yeah. That's, I think, the mark of a quality entry is when it's inferable, but still becomes an interesting piece of trivia. And then is there any feel that you have strong feelings about either positively or negatively?
00:49:46
Speaker
This is the space to vent. I have so many opinions on fill. We could do a whole podcast on that. but so I like a good mid-length fill that's just like a cool evocative word. I was very, very happy when I got the word Zephyr into a puzzle because that's just such a great use of a six-letter slot.
00:50:05
Speaker
And there's so many sixes that are mediocre that get suggested all the time if they're on your word list, like ah SLN or any of those ones that have four vowels in them. Oreo O's.
00:50:15
Speaker
Yeah, Oreo O's, exactly. i mean, ah speaking of those, I love awooga because awooga is just a fun word, but it's also an incredibly useful word for the second column of a crossword.
00:50:26
Speaker
I'm kind of tempted to make my ringtone just be you saying awooga over and over. hey
00:50:35
Speaker
And then for listeners who are just getting started, what kind of advice would you give to an aspiring constructor? Again, i would say solve a ton and construct a ton.
00:50:48
Speaker
Construct stuff just for yourself, just for the sake of getting better at it without an eye to publication. I think especially when you're starting out, it's great to just write puzzles where you have no intention of ever publishing it.
00:51:00
Speaker
So you can do whatever kind of theme or themeless or whatever you want. Like you could do the most overused theme of all time and just fill it to see how it works to fill a puzzle. Yeah. And then going along with what you were saying earlier, if you're intimidated by grid construction, maybe just borrow someone else's and adapt it a little bit to make it your own, but don't feel like you have to reinvent the wheel.
00:51:21
Speaker
Yeah, absolutely. And what kinds of venues would you suggest for an early constructor? A lot of people have said universal, I think, and I totally agree with that because A, they respond very quickly and B, they give detailed feedback. But I would also say i'm wary of recommending a venue just in and of itself because I think always you should tailor your submissions to whatever venue.
00:51:44
Speaker
So i recommend solving all the venues that are out there and getting a sense of what works best at each venue. And then whenever you have an idea, tailor the idea from the get-go as much as you can toward the venue that it seems best for.
00:52:01
Speaker
And I do realize that that's a risky strategy. Well, they might reject it. Puzzles get rejected a lot. And now you've got a puzzle that you've written for the New York Times or whatever that the New York Times doesn't want. And you might want to try to shop it elsewhere.
00:52:15
Speaker
In that case, of course, you can always rewrite the puzzle. I know it's a lot of work, but it's worth it. And you don't have to completely rewrite the puzzle, right? And I think it also sort of shows respect to the editors, the fact that you've read, you've internalized their style guides and their guidelines.
00:52:31
Speaker
So what you're submitting to them feels like you've written it for them, even if you have sent it to four other venues already. Yeah, that is very wise. And do you have any crossword goals for the future?
00:52:43
Speaker
think I know one of them. I mean, yes, I would love to win the ACPT, although i am trying not to put too much stock in that because I think it's an extremely plausible situation that Paolo just wins 15 in a row.
00:52:57
Speaker
And by that point, I'll be over the hill. LAUGHTER In terms of constructing, I would say i want to collaborate more again. i collaborate less now than I used to, partly because I'm busier and I want to collaborate with more people.
00:53:13
Speaker
It's a great way to learn from constructors with different styles. So that's my main other goal. Makes sense. And is there anything you hope to see change or emerge in the world of Crosswords in the future?
Future of Crossword Construction
00:53:24
Speaker
I very much like the trajectory that the crossword world is going on these days with respect to things like inclusiveness and people being thoughtful about fill and diversity among constructors and editors and that sort of thing. And I hope those trends continue because there's still a long way to go with that.
00:53:44
Speaker
I also hope in general that There continues to be room for venues that are willing to do weird and wacky stuff. And maybe there'll be more such venues in the future. Like I love when I open an AVCX puzzle and it's something zany that I haven't seen before.
00:54:02
Speaker
RIP to Crucianova. I loved when that venue was around because they were there deliberately with the purpose of courting the weirdest and most boundary pushing puzzles they could find. And it doesn't have to be as radical as all that, but i just hope that the trend continues of people being willing to push the envelope in terms of weirdness and things that the constructor loves, which aren't necessarily the most popular things in the world.
00:54:30
Speaker
Yeah, absolutely. We always need more weird and wacky because so much has been done already. And if you can still find a way to push the boundaries and surprise us, that is a pretty impressive feat.
00:54:42
Speaker
Yeah. So that is everything that I had for you today. Is there anything else you'd like to share with our listeners? I don't think so. Thank you so much for having me. This has been a blast. Yeah, no, thank you so much. I've learned a lot and it's been great talking to you one of my favorite constructors. Thank you so much.
Episode Conclusion
00:54:58
Speaker
All right, this is Daniel Grinberg with my special guest, Will Nedeger. Thanks so much to Will for joining me today. And thanks so much to all of you for listening to Lucky Episode 7.
00:55:10
Speaker
Hit me up with any feedback or ideas you might have at the crosstalkpod at gmail.com. And join me again next time for another constructor conversation coming your way soon.
00:55:22
Speaker
Until then, wishing you inspired constructing and happy solving.