An Interview with Caleb Shenk, Winner of the 2022 Crossword Scholarship

Winner of the 2022 Crossword Scholarship

After another year of competitive puzzle submissions, we were delighted to connect with Caleb Shenk, the winner of the 2022 crossword scholarship. Visit our 2022 Scholarship Winner page to see all our finalists.

Read on to hear more about his experience with crosswords, journalism, and advice for aspiring cruciverbalists.

Can you tell us a little bit about your crossword creation process?

Making a crossword has four major steps — theme, grid construction, fill, and cluing — and my favorite part of this grid was certainly the theme. I toyed with a tennis-themed crossword, but couldn’t come up with wordplay that I liked. I then thought about my work with our college newspaper, and how I’m going to work with the digital aspect next year. I thought of an “eNewspaper” idea, and how adding an “e” to words could create new words that related to a newspaper. (It ended up working better to have the revealer be ENEWS, rather than eNewspaper.)

Once I had that seed in my head of what I wanted to create, I went on a walk around campus with a notebook in my hand and tried to think of words that would fit my theme material. I find that walking can help me brainstorm, and I didn’t let myself go back inside until I had four options. I ended up with four words that fit the criteria: relating to a newspaper, having the letter “e,” and creating an etymologically distinct word if the “e” was removed. It was a small list, so I’m glad it worked out. I then went to, and found phrases with the “e”-removed words, and went from there.

One hard part of the process was the fill. I generally don’t mind it, but it just happened that twice, I started cluing my grid but then realized I had to rework my fill. The first time I realized I unintentionally had two obscure words crossing and had to redo about half of the grid, and the second time I realized I had accidentally included 80 words in the grid, when 78 was the maximum. So, I had to redesign the entire grid, which wasn’t super fun, but I’m happy with how it turned out.

You were a finalist last year, too. What’s your experience been with this contest?

Yeah, I was a finalist two years in a row, which was fun knowing that I was close, but also was certainly a motivator to see if I could get to the next level. I put more work into the theme this year than in years past since last year I didn’t really have anything special to my theme. It’s nice to make a well-constructed crossword within a certain topic, but I noticed that last year’s winner really elevated his puzzle by adding wordplay to a cohesive topic. So this year, I really dug into my theme material and tried to see what I could come up with, and I think that this year showed that additional layer of wordplay I was looking for.

Also, after I submitted my crossword, I realized that completely by coincidence, last year’s winner and I both included BATMOBILE which was fun.

What kind of crossword puzzles do you like to solve? Anything you don’t like to see in crossword puzzles?

I love crosswords where the grid does something special. One of my all-time favorites is a Thursday in the NYT by Herre Schouwerwou that I think is just a masterpiece. In general, I look forward to Thursdays while remaining on alert that rules may be broken. The bigger the “aha” moment, the better.

I’m not a huge pun guy, just because they’re often hard to clue and I think it’s hard to make people laugh through a crossword.

How often do you write your own crosswords?

Not as often as I’d like. I do a weekly 5×5 for my college newspaper, but I’ve only gotten to around two or three full-size puzzles in the past year. I’ve gotten a lot better at the mini crosswords, but a full-size one is quite a different challenge. I have a few ideas in the hopper that are at different points in the submission process, but hopefully this summer I’ll have time to bring them to fruition and try to get published.

Can you tell us more about your experience with your school newspaper, The Record?

I’ve done work in various roles at The Record, including staff writer, opinion editor, and news editor, and I will be digital/managing editor next year. I’ve written articles since my first semester of college, and I debuted, to my knowledge, the first crossword column. When I had my first opinion piece published in The Record on entering college amid a pandemic, I was enthralled with the process of writing on a deadline, submitting it, and the editing process — and then getting feedback from my peers, community members, and even our college president helped me realize the newspaper’s wide-ranging influence. Having one’s words turned into printed ink on a page, and simultaneously etched into the college’s first draft of history, is a daunting, humbling, and yet remarkably fulfilling task.

Do you have any advice for people who are new to writing crosswords?

I think it was Stephen King who said that if you want to be a great writer, you should do two things: “read a lot, and write a lot.” My advice for crossword constructing would be very similar: solve a lot, and construct a lot. Constructors should solve a lot of crossword puzzles to first learn what the crossword rules are, and how good constructors sometimes break them. Getting a feel for what a good theme, fill, and cluing looks like is essential to being able to create one’s own crossword — I solved crosswords for about a year before I realized that I wanted to start making some of my own.

And then, once you’ve solved a lot, it’s time to construct a lot. As soon as you think of a possible theme, write it down. Even if you don’t have time to fully flesh it out, get it written down so you can come back to it. Once you’re ready, start making the puzzles. The best way to get a feel for where to place black squares and how to choose theme entries is to try it. Constructing is a skill that you have to practice, and it’ll get better as you learn what works well and what doesn’t.        

Also, a good word list can be incredibly helpful in creating a good crossword. It’s worth investing in a good list, whether by purchasing one online, and/or adding to the list with phrases you find.

 Do you have any shout-outs or people you’d like to thank?

I have a trusty trio of crossword lovers — my mother, and friends Mia and Jadyn — who loyally solve my mini crosswords in the newspaper and also gave great feedback when they test-solved this scholarship entry before I submitted it.

Before all that, though, was my mom, Jen, who got me into crossword solving. I would see her solve them as a little kid, and my amazement with how she churned through the grid spurred me to start solving them in high school. I’m also appreciative to anyone who solved my little crosswords on campus; it is a joy to hear solving stories and encouragement from friends.

Is there anything else you wish we’d asked or you would like to tell us about yourself?

I’m very grateful to My Crossword Maker for the scholarship — college is a large financial investment, and I’m incredibly appreciative for their contribution to my education. I encourage everyone to apply for this scholarship as often as you can, as well as all other external scholarships! It could be well worth your time.

Thank you, Caleb, for your thoughtful answers and your clever puzzle, and congratulations again on your big win! 

Want to give some of his tips a trial run? Visit My Crossword Maker to start building today!

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