Not many engineering grads can say their career led them to one of Canada’s largest media organizations, creating crossword puzzles. As The Globe and Mail’s puzzles and games editor, Jess Shulman had a path that has been anything but conventional.
After building a successful career in communications, writing, and editing, the electrical engineering and society graduate discovered a passion for crossword construction that ultimately transformed her professional life. A proud McMaster Engineering alumna, former McMaster Engineering Society president and founding member of the McMaster Engineering Musical, Shulman reflects on her undergraduate experiences that helped shape who she is today; her unique career journey and unexpected opportunities; her process for constructing crosswords and a day in the life in her dream job.
Your job sounds really interesting! Can you walk us through how you went from studying engineering at McMaster to becoming The Globe and Mail’s puzzles and games editor?
It’s been a bit of journey! My degree was in Electrical & Society, and it was the “society” part I loved the most—engaging with the broader world, reading and writing, exploring a wide range of topics.
I was hired through on-campus recruiting to a sales role at GE Healthcare, which seemed like the best combination of really cool technical content (selling MRIs and CT scanners) and working with people. I was thrilled to get the job, and I loved the company and the people I met, but it turned out I was really not built for sales. I was really quite bad at it, actually; I was never comfortable with the constant need to close deals and hit targets.
As I worked to figure out what I wanted to do next, I came back to my long-time love of reading and writing. I enrolled in some part-time journalism courses at Ryerson University (now TMU) and began steering my career toward writing and editing. Over the next many years, I ended up holding proposal-writing and communications roles at organizations including GE, Aon Consulting, and Deloitte.
Wanting to focus more on editing, I pursued Editors Canada’s Certified Professional Editor designation. With the CPE under my belt, and after 17 years in the corporate world, I launched a freelance business, editing fiction and non-fiction books while continuing corporate writing and editing work. I loved the variety of projects and the flexibility it gave me, and I assumed that would be my final career move, something I would happily do for 25 more years. Turns out I only did it for nine.
What changed for you?
During COVID, some people learned to bake bread; I learned to construct crossword puzzles.
Soon I had puzzles published in most major North American venues, and I became deeply involved in the crossword community. One day, out of the blue, Fraser Simpson (one of North America’s premier cryptic crossword constructors) contacted me about a potential opportunity at the Globe and Mail. 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 possible 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 out there! After an initial call, I began informally advising The Globe on all things crosswords, and eventually they asked me to officially consult on the project and start soliciting puzzles. 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’s puzzles and games editor in January 2026. I can hardly believe my luck.
When did your love of games, puzzles, or wordplay first begin? Was there a specific moment, person, or experience that sparked that interest?
My whole family has always been really big on puns and dumb jokes, so the love of goofy wordplay was bred into me from day one. Fun fact: throughout the 1990s and early 2000s, my grandfather (K.C. Angus) was one of the most frequently published contributors to “The Challenge,” the Globe and Mail’s weekly wordplay contest run by Warren Clements. He had so many published that my parents had them bound into two hardcover volumes.
I also always think of my grade nine math teacher, Mr. Spiering, who used to give us logic grid puzzles to do if we finished our work early. I loved those.
It took me longer to come around to crossword puzzles. That same grandpa used to do the New York Times puzzle every day, and he was so well-read and clever that I think I assumed they would be beyond me.
As a (younger) adult, I started solving Kathleen Hamilton’s “North of 49” puzzle in the Toronto Star on Saturdays, and I’d sometimes pick up a book of easy crosswords at the airport. But it was only during COVID, when so many games were exploding in popularity, that I really got the bug. I joined in with everyone doing Wordle and all the rest that followed, and most of all I committed myself to learning to solve NYT crosswords, starting with a whole bunch of Mondays from the archives, then Tuesdays, etc.
It didn’t take long before I started wondering how the crossword got made. My time from becoming a dedicated solver to starting to construct was maybe six months; by the next year I had started solving and constructing cryptic crosswords as well. I dipped a toe in and got hooked!
I had my first New York Times puzzle published in 2022 (I’ve had two more since then), and I’ve had others published at The Walrus, USA Today, the LA Times, Universal Crossword, Apple News+, and some really great indie venues: AVCX, Puzzmo, the Inkubator, and the Browser. And now the Globe and Mail!
Of all the games and puzzles you work with, do you have a favourite? What makes that particular game so compelling for you?
The crossword! I really enjoy the huge range of daily quick-hit games and puzzles that are out there these days, and I look forward to bringing new games to the Globe and Mail audience over time, but as a solver, a constructor and an editor, crosswords are my true love.
First of all, every puzzle is different. They offer so many possibilities for variety, through interesting grid entries, clever themes, fun clues. A constructor can really put their own voice into a crossword, which makes every puzzle distinct. Of course I love that they’re all about words and wordplay. I also really love the precision of a grid, the rules of cluing, the technical side of using construction software. Crossword construction tickles so many parts of my brain.
At the Globe, the crossword is also where we can really showcase Canadian entries and clueing angles, as well as Canadian constructors. In February we launched our new Saturday crossword, The Weekender, which is made in Canada exclusively for us by an amazing group of home-grown constructors. Our Saturday cryptic crossword has been Canadian-made for 30 years by Fraser Simpson, and it’s now available online as well. I also personally make our daily mini crossword, and I fill it with Canadian spelling and references whenever I can. We have plans to keep expanding our lineup; I can’t wait.
Looking back on your time at McMaster Engineering, what experiences, courses, projects, or people had the biggest impact on your personal and professional development?
My best friend and housemate, Tina Traini, and another friend of ours, Eloise Harvey, had this wacky idea that engineers could be convinced to sing and dance on stage. They recruited some other very brilliant and creative folks, and I was lucky enough to be along for the ride.
In 1999 we were the founding cast and crew of the McMaster Engineering Musical – which I’m very proud to say is still happening every year, 27 years later!
The two shows we did (“Jopko and the Amazing Technicolour Vector Space” and “West Quad Story”) are among my absolute best Mac memories.
I was also a Redsuit every year and was on the McMaster Engineering Society, including as president in my last year (’99/’00). Engineering is an intense, time-consuming program, and doing all these extracurriculars was a necessary stress reliever and a great way to spend time with classmates beyond studying and lab work.
One other thing: I met my husband at an Eng Pub. It was at “The Rat” (The Rathskellar pub that’s no longer there); he wasn’t an engineer but he happened to go that day, and the rest is history – we’ve been together for 30 years, married for 25 this fall. His brother and my sister also went to McMaster – we’re a proud Mac family!
What does a typical day look like as The Globe and Mail’s crossword and games editor, and what might surprise people most about the work behind the puzzles readers enjoy every day?
I think people might be surprised to learn how much work goes into creating a crossword puzzle. A big part of my job is editing the Weekender crossword, which starts with submissions from our roster of Canadian constructors. Each one comes in as a theme idea; I might approve (or reject) it right away or help the constructor refine it. Next they send me a filled-but-unclued grid, which I review for any words that feel too obscure, crosses that seem too difficult, or duplicate entries. We often go through several rounds of revisions before they send me their full puzzle with 140+ clues.
That process can take weeks, depending on how much rework is needed, as well as the constructor’s availability, since they’re mostly freelancers who make puzzles on the side.
Then each week I thoroughly edit one finalized puzzle, reviewing every clue for accuracy, difficulty, variety, spelling, etc. I also make a week’s worth of the Globe Mini crossword each week; I try to make two a day, working a few weeks ahead. At the end of the week I package up the Weekender and seven Minis and send them to our team of testers.
Earlier in the week I’ll have received testers’ feedback on a previous set of puzzles. They flag clues that seem confusing, unfair, or too difficult. They also routinely catch factual issues and even typos – as every editor well knows, you always need more pairs of eyes! I’m so grateful to have testers.
The rest of my week is spent processing puzzles from our syndication partners, proofreading and posting Fraser Simpson’s Saturday crypticsconsulting with our digital team, answering reader emails, and working on Puzzle Pieces, my weekly column that appears each Saturday in the Globe‘s Life section online.
What advice would you give current McMaster Engineering students or recent graduates who are interested in pursuing careers outside of traditional engineering roles?
Just don’t be afraid to try new things, take new opportunities, and raise your hand for something that interests you. Also, careers are long. There’s no rush, and there’s lots of time to get it wrong now and then. I don’t know anyone who’s doing the job now that they started doing at 22 or that they ever imagined they’d be doing at 50, and hardly anyone I know is using their degree directly, to be honest. And the world is changing at light speed – the jobs of the future don’t even exist yet. So just go into the working world with your eyes open, explore, be curious, and see what happens. You never know when someone will call you up and ask if you’re interested in a job.