This month we’re featuring cryptic and American-style crossword constructor and editor Jess Shulman (she/her). Jess lives in Toronto, Canada.
Jess! You have some exciting career news to share. Will you tell us about that?
Yes! I am now The Globe and Mail’s Puzzles and Games Editor!
Before this, I spent 17 years in various corporate roles before leaving to start a freelance editorial business after earning my Certified Professional Editor designation from Editors Canada. I loved freelancing, did it for nine years, and assumed it would be my final career move.
Then, completely out of the blue, Fraser Simpson (one of North America’s premier cryptic constructors) contacted me about a potential opportunity at The Globe and Mail, Canada’s national newspaper. The Globe was planning a major games revamp and was going to be hiring, and they’d asked Fraser to ask around for some names of potential candidates.
If you’d asked me the day before if there was any job in the world I would go back to 9-to-5 office work for, I’d have said no way. Little did I know this job was going to come along!
After an initial call I began informally advising them on all things crosswords. Eventually they asked me to officially consult, and then a few months later when the job was finally posted, I was already more or less doing it. I wound down my freelance business and started as The Globe and Mail’s Puzzles and Games Editor this past January.
So exciting, Jess! Congratulations. Can you tell us a little more about The Globe and Mail’s games and what a typical day looks like in your new role?
We launched a new app in February, and it’s still evolving. Right now, the highlights include a daily mini crossword, which I construct, and “The Weekender,” a 21×21 Saturday crossword available online and in print, which is made by a roster of amazing Canadian constructors. Both of those use Canadian spelling, more French than Spanish, and Canadian cluing angles wherever possible. We’ve also brought Fraser’s weekly cryptic online, where it was previously available only in print.
My job is pretty varied. I handle submissions and edits for the Weekender, including the workflow of having puzzles tested and posted and preparing the Weekender for print. I proof Fraser’s puzzles. I manage the syndicated puzzles we run. I am constantly making minis. I respond to reader, ahem, feedback… of which there is A TON. And I’m heavily involved in ongoing discussions about what the next phases in the app will look like. I’m having a great time.
What do you love about puzzles?
I love the joy of figuring something out, the sense of satisfaction at cracking a code. It’s especially fun to solve with other people (like in puzzle hunts or escape rooms or group cryptic solves), one idea building on another, everybody’s brain contributing something else until you solve it together. I also come from a family that really appreciates wordplay and puns of all kinds, and my parents and sister and I are all writers and editors, so there’s a lifelong love of words that’s deeply entrenched.
How did you get started solving and constructing them?
I was a casual solver for years. I used to solve the “North of 49” crossword by Kathleen Hamilton in the Toronto Star or pick up a book of easy crosswords at the airport. My late grandfather was an avid NYT solver (and a great lover of puns and wordplay), and he was one of the smartest people I knew. Somehow, that made me think that harder puzzles were not for me. I wish I’d thought to try them sooner! It was only when COVID hit, my grandfather having died the year before at age 99, that I finally decided to try to learn to do them.
Shortly after, in October 2020, I messaged my friend Sara Goodchild. I knew that she’d been learning to construct cryptics, and while I was sure *those* were waaaaay beyond me, I told her I’d love to learn more about how crosswords get made. I wasn’t planning to become a constructor myself, I genuinely just wanted to learn more. But then I started reading through the whole list of resources she sent me, and the rest is history. I was hooked on the spot. My first published crossword was in Universal on August 14, 2022.
Did you find a mentor to help you along the way?
Yes! I put my name in for one on the Crossword Puzzle Collaboration Directory and was thrilled when Robyn Weintraub emailed me! Robyn was a huge help in my early days; she would gently tell me when things didn’t work, or that no, there was really not a reason why my particular theme would justify 84 words in a grid.
I think one of the big things that every new constructor needs to learn is to keep working a theme or a grid until it’s really good. At first it all feels so hard, and it’s easy to convince yourself “I have literally found the absolute best (or only possible) fill for this corner,” and yet when a mentor looks at it and suggests you take another run at it, you almost always see that, oh right, a little extra effort *can* produce better a result. Robyn’s early critiques helped me develop that sense.
What other experiences have helped shape your approach to constructing (and editing) crosswords?
I think the thing that’s had the biggest impact on me as a constructor and editor has been editing for Lil AVCX. Lil AVCX is designed and run as a training ground, both for new constructors and for new editors. A roster of new constructors is chosen for a year, and they get mentored by a roster of editors, who are in turn mentored in editing by the leadership team. I’m now in my third year and final year as an editor at Lil, and it has really helped me learn all the different aspects of editing – from assessing theme ideas, to evaluating grids and guiding revisions, to editing clues, copy editing, etc.
The Lil community itself has been just as valuable. We have a very chatty Discord group where we regularly workshop ideas and share memes, pictures, and life events. It’s been such a lovely experience to be part of this group.
That also enabled me to step on to the editorial team for AVCX Classic. For the last couple of years, I’ve participated in evaluating submissions that come in to Classic, and I’ve learned so, so much from that team about what makes a really strong theme and grid – as well as what makes a good response, as there’s a big push in that group to provide helpful feedback in a rejection email.
What makes a strong theme? (Asking for a friend…)
This is such a tough question, but I’ll try to lay out some thoughts:
- Tightness: You want the themers to clearly make a set, there shouldn’t be one weird outlier, they should be more or less equally funny or clever, they’re balanced.
- Freshness: The themers should be new, fresh, fun, surprising, clever and interesting to discover in a grid.
- The revealer is key: For themes that have a revealer, it should really deliver an aha-moment.
- 21x (which is what I mainly work on at The Globe): Evan Birnholz did a great session at Crossword Con last year about 21x puzzles, and his conclusion was, “a great Sunday-sized theme is whatever you want it to be.” I love that perspective. I do think it’s important to keep in mind that because the puzzle is that much bigger, to sustain a solver’s interest, it should ideally provide continual surprises. It can feel like a slog to solve if you have eight or nine themers that are all the same thing. I think the best 21x themes take a joke/mechanism/idea and then have each themer put a new twist on it, or interpret it in some new way, or somehow contribute incrementally to the whole.
- Cleanliness: No matter how good your theme set is, it only works if it’s supported by a strong, clean grid. I so clearly remember as an early constructor feeling that it was literally not possible to find better fill given the constraints of my theme… but I have learned that that’s rarely the case. There’s usually a way to move themers around, move blocks around, etc.
You strike me as someone who especially enjoys themed puzzles. Is that accurate?
Yes! I lean toward themes, because I find them the most fun as a solver. I especially enjoy “Thursday” type themes and wish I had more ideas for them! I also love constructing cryptics, even though it takes so much longer – there’s something sooo satisfying about coming up with a good clue.
Yes, let’s talk cryptics! How did you get interested in solving them and what inspired you to start making them? For readers who may be new to cryptics, can you give us a quick introduction?
At first, cryptic clues (seem to) make absolutely no sense. The important thing to understand is that every cryptic clue is its own little puzzle. There are rules and conventions and tricks that you learn over time.
Each clue is made up of two halves: 1) a definition, and 2) wordplay. Separately, each of those halves is its own clue to the answer. The trick is, you don’t know which half is which, or where the separation is, because the clue is written in such a way that the “surface” meaning almost makes sense as a complete phrase. So that’s something you’re always trying to figure out – which half is which. The wordplay part breaks the entry apart into its letters and gives you hints as to how to assemble the letters to make the entry. Solvers have to sort out how those parts might go together to make a word that can satisfy the definition half. AVCX has a really nice how-to doc for solving cryptics.
I can’t really remember what got me interested; I assume it was Sara’s influence, once again. It was a bit like my regular puzzle solver-to-constructor journey in that there wasn’t a huge gap between those two stages! Once I started solving a few, I couldn’t wait to start constructing.
The first real cryptic construction I did was for a charity pack called Grids for Kids, which raised money for children’s charities. Around that same time, I submitted a small sample of cryptic clues to AVCX Cryptics and after tons of help and feedback, I’ve now constructed five cryptics for them.
Where are you published?
I’ve published in most of the major venues, though I’m not super prolific like some people – in most cases I’ve had one or two, maybe three, published at any given spot – NYT, LAT, Universal, Puzzmo, AVCX, Lil AVCX. I’ve done quite a few for The Walrus, a Canadian magazine, and now a hundred thousand minis for The Globe and Mail. I also construct cryptics, as I said, which I find a) the most satisfying/rewarding and b) the most utterly exhausting to construct! When I’m in the middle of doing a cryptic, I tend to drop everything else for the duration. I’ve had several cryptics at The Browser, AVCX, WSJ, TPFA, and Cryptic Crossweird.
Do you have a few favorite puzzles or clues you’d share with us?
I’ll always be very proud of my NYT from Thursday, March 22, 2022. I was so proud to have it accepted, and it got such a positive response from solvers. (And it was a Thursday!)
Now I’ve constructed nearly six months worth of daily minis for The Globe and Mail. There’s no paywall on those (yet?) so I hope people will take a look. I’m having a ton of fun writing very Canadian clues whenever I can fit them in, like these:
- [A “regular” coffee at Time Hortons contains this and 2-down] – CREAM and SUGAR
- [Pick up a ___ for May ___ (grab a case of beer for the Victoria Day long weekend, no matter what days it actually falls on)] – TWO FOUR
A few cryptic clues I like (although every clue I ever write is my baby):
- [Wow! A puzzle! (5)]
- [Staring down a pitcher of refreshing Labatt, overlooking lake (2,3)]
- [Wanna laugh after opening of soda? Shake well (5,2)]
Whose puzzles do you always make time to solve?
I admire lots of constructors, but honestly, I most often seek out puzzles made by people I know. There is something really cool about solving puzzles by friends – it’s rather amazing to think that we’re all connected in some way by solving each other’s puzzles.
Just in general, the people and constructors I’ve met because of crosswords have been so amazing. My crossword story wouldn’t be complete without mentioning Amie Walker. She was one of my first crossword friends and encouraged me to go to ACPT, which has become a can’t-miss annual event. (So, obviously, I love solving her puzzles!)
Any crossword resources to shoutout?
I’m a huge fan of Ingrid – the ability to approve multiple words for a given slot has absolutely changed my constructing life.
I’ve made a big effort in the last couple of years to personally score my wordlist, especially all the three- and four-letter words (and I’ve made a good dent in the fives too). I do a lot of scoring while I’m constructing and editing, too. I spent several years saying “I know you’re supposed to work on scoring your wordlist but I’ll never have time for that and it’s fiiine,” but now that I have done it, I can’t recommend it enough!
How have crosswords changed your life?
Well, since they’ve now become not just my hobby, but also my full-time job, I guess that’s the answer to the question! They’ve also become my source of so many friendships, people that I look forward to seeing at ACPT every year, people I talk to online all day… It’s just a really absolutely massive part of everything I do. I think my grandpa would be proud.
When you’re not making and editing puzzles, what do you enjoy doing in your free time?
I love reading, especially audiobooks. I attend Puzzled Pint and other puzzle hunts/events. For years I also spent weekends as a baseball mom, traveling across Ontario and the northeastern U.S. for tournaments. With my youngest about to finish high school, I’m about to become an empty nester, but the baseball life will continue as he’s playing at university this fall.
A little over ten years ago, some friends and I started a cover band called Ladies & Escorts. We play a couple charity shows a year, centered around three-part harmony, and cover everything from Dolly Parton to Taylor Swift to Crosby, Stills, and Nash. It’s been a huge source of joy and friendship in my life.
I am also focused on fitness; especially now as I’m about to turn 50, I’m very passionate about staying strong and mobile as I age. I’m hooked on Sydney Cummings’s at-home strength programs (free on YouTube!), so I try to work out with her four or five times a week, and I also try to do hot power yoga once or twice a week. I love going for hikes and paddle boarding, too.
Rapid-Fire Round:
Constructing or solving?
Constructing (if I *have* to choose)
Best part of singing?
It just feels so good to make that cool sound as a group – there are certain songs that have maybe one really cool line or chord that just somehow feels so incredible when we hit it right, I get goosebumps.
Daily step goal?
10,000/day *on average* over the month
Favourite colour (yes, I spelled the words that way just for you!)?
Not sure I have a favourite colour… but I appreciate the opportunity to use Canadian spelling! Pet peeve: could American constructors please clue “zed” as Canadian rather than just British?!
Go-to emoji?
I like the blushy smiley face 😊
Favourite food?
Indian or Mexican
😊 😊 😊😊😊😊😊😊😊😊😊😊😊😊😊😊😊
This interview has been edited and condensed.
Jess Rucks is a crossword constructor and play therapist. She loves combining her curiosity about people with her passion for crosswords in DCL’s Constructor Spotlight.