An enigmatic career: Math alum is Wall Street Journal's puzzle guru

Editor's Note: This story was originally written for Russ Eshleman's COMM 474 Depth Reporting course in the College of Communications.

Inside a boxy Manhattan office – surrounded by bookcases littered with magazines, dictionaries and encyclopedias – Mike Shenk hunches over his desk and pecks the keyboard of his double-screen Mac desktop.

Shenk is doing what big-city commuters, diner patrons, college professors and your Uncle Charlie do every Tuesday morning with a pencil and steaming mug in hand.

He is solving a crossword puzzle.

He is also working.

Shenk, 56, is a puzzle creator and the crossword editor of The Wall Street Journal. He’s a Lancaster County farm boy with a Penn State math degree who decided decades ago that he would rather stump everyday people with words and puzzles than challenge high school students with numbers and equations.

As one of three partners who run Puzzability, a puzzle-writing company, he can see his handiwork in the boxed calendar sets resting on office desks across the country, on the U.S. Navy’s Facebook page, and in magazines in the netting on the backs of Amtrak seats up and down the East Coast.

What most people do as a hobby, Shenk does to pay the bills.

Shenk, now one of the country’s leading enigmatologists, was never trained in puzzle creation, nor did he seek help from experts. He learned his craft through observation and by relying on his greatest asset, his brain.

The boy who once paged through his mother’s puzzle books on the family farm carried his interest to Penn State. There, in the late 1970s, he was the first person to construct daily crosswords for the student-run newspaper, The Daily Collegian.

In his college days, he yearned to be able to earn a living in puzzles. Concluding that it was an impossible dream, however, he focused on a more conventional career: teaching math. He began his first teaching job in rural York County in 1979.

Barely a year later, finding that his teaching bored both him and his students, Shenk began submitting puzzles to Games magazine. He described Games as a publication known for “obscure, tricky” puzzles rather than the typical “dry, educational” variety.

The connection to Games proved to be pivotal – his work came to the attention of a rising enigmatology superstar, Will Shortz. When the magazine expanded and needed to hire more editors in 1981, Shortz, one of the editors, threw Shenk’s name into the mix. After a trip to New York City and an interview, Shenk had a job in the world of puzzles.

Shenk created and edited puzzles for the bimonthly magazine until it went out of business in 1990.

Shenk found work elsewhere, including a six-month stint at Dell magazines as a puzzle editor. A year later, Games returned, as did Shenk’s job.

He continued to produce fresh puzzles for the next five years before the company officials decided to move operations to Blue Bell, Pennsylvania, in 1996. Shenk, who lived in New York, was jobless again. Not long after, he and two former Games colleagues, Amy Goldstein and Robert Leighton, kickstarted Puzzability out of his Manhattan apartment.

The Wall Street Journal soon came calling.

Since then, Shenk said, his workload has grown, his puzzles have strengthened, and his craft has become his life.

The hobby that attracted him with its playfulness, variety and entertainment has evolved into a flourishing career. It is a career that any puzzle-lovers would envy, and it is one that he does not need to be coaxed out of bed for.

The puzzle guy at work

Warm October air blows through the tall windows of the Puzzability office as Shenk’s lean frame perches at his desk. His black and red Nikes are wrapped around the wheels of his chair; his hands lay cupped in his lap.

A stack of No. 2 mechanical pencils rests to his right. Their pink erasers are rubbed raw to a nub.

“Pen or pencil?” he is asked – the question any crossword puzzle solver would ask an expert puzzler.

“Pen,” he replied, adding that he doesn’t often solve puzzles as a leisure activity.

“It’s kind of like a busman’s holiday,” he said. “The Saturday puzzles don’t usually stump me. I’ve been making and solving puzzles so long now that I know most of the tricks.”

In his own estimation, Shenk may not be the fastest solver but he is unchallenged by even the trickiest puzzles.

“When I solve crosswords, I usually try to solve them with just the downs. I don’t look at the across clues,” he said. “As a crossword constructor, I can sort of see words forming across that I don’t need to look at the clues. I can just say ‘I bet this is going to be ...’ and that helps me get the downs.”

The trick to solving the puzzles, in many instances, is understanding the clues and how they are worded. For example, if the clue is “the day after Wed.,” the answer would be “Thurs.,” because both days are abbreviated.

Other clues are obvious to frequent solvers, such as clues and answers using the same parts of speech and plural clues leading to plural solutions.

“There are some words that come up much more in crosswords than in real life and some words that come up nowhere in the world but crosswords,” Shenk said.

“Etui” (“an ornamental case for small articles,” according to Webster’s) and “ogee” (“a molding having an S-shaped curve”) would be examples of the latter; “Oreo” (the cookie) and “emir” (an Islamic ruler) would be examples of the former. Shenk said editors and constructors often try to avoid these.

While his solving skills may be down pat, Shenk spends most of his time creating and editing puzzles.

Shenk’s life can be described as more work, less play.

His bachelor pad, a few blocks from his office, easily transitions into work space.

Despite being surrounded by one of the largest nightlife centers in the world, Shenk, a self-described introvert, said he doesn’t participate in Manhattan’s hustle and bustle.

When he decides to take a night off of editing and designing for Puzzability and The Journal, Shenk is likely to be watching “The Walking Dead” and “Dr. Who” on television. He gets together with buddies on Friday nights to play card games such as Guillotine – a game set during the French Revolution, where, Shenk said, “the point is sort of to make the other players miserable.”

“My favorite thing is to just have time to myself,” Shenk said. “I’m not a hugely social person. I don’t go out and do night club stuff, and I don’t go to shows too often.”

A nice thing about puzzles as a career, he added, “is it’s also fun, so it’s also my main hobby.”

How he got started

Beneath Shenk’s peppery hair and furrowed brows is a mind that works in a constant stream of letters and clues.

Words are not just words, and phrases are not only phrases. Both are arrangements of letters waiting to be plugged into the white cells of crossword puzzles.

“My mind probably works a lot different than everybody’s,” he said. “I’m very often thinking puzzles. Any free time, I’m playing with ideas and trying to come up with new themes for crosswords.”

Shenk said that is not uncommon for puzzlers. Ideas stick in their heads and become fixations.

“For me, it’s counting the number of letters in phrases and saying, ‘Oh, that would be a good length for a daily puzzle,’” he said. “We puzzle people find ourselves always looking at words as things to manipulate.”

This is a quirk that propelled his puzzle-making from a childhood hobby to a career.

Shenk’s interest in crosswords was sparked at his farm home in Manheim. His mother, Joan, liked to buy crossword-puzzle books, and she started leaving some of the puzzles for him to solve.

Joan Shenk recalled that her son became interested in puzzles as soon as he was a good reader, far ahead of his classmates. While other boys signed up for tee-ball and played in packs, Mike opted for composing games and puzzles for the family. Often he could be found designing mazes of hay in the family’s barn instead of doing his assigned chores.

“I enjoy my job now doing cerebral stuff, but I was very lazy and I wasn’t very happy to be doing the actual physical work as a kid,” he said. “I did a lot of work but never really enjoyed it.”

His passion for numbers and logical thinking drove him to pursue a degree in mathematics at Penn State.

At the end of his freshman year, Shenk opened his college newspaper to find an ad for a job that would become a stepping stone in his career.

The new editor-in-chief of The Daily Collegian was calling for someone to create crossword puzzles, and Shenk was up for the job.

As he remembers it: “I said, ‘Ooh! I’m going to give her some samples.’ So I gave her some samples and she said, ‘Sure!’”

Shenk went on to make five daily puzzles each week over the next three years. That output far exceeds that of professional crossword-puzzle creators. Today, in an average week Shenk creates three to four crosswords and edits about three more.

Shortz, who is now the crossword puzzle editor of The New York Times and puzzlemaster on NPR’s “Weekend Edition,” is still amazed by Shenk’s puzzle production as a college student. “There have been lots of people over the years that make crosswords for their college newspapers, but it’s usually been weekly or less frequently,” Shortz said. “Mike is the only person I’ve ever known to do it daily. It’s astonishing.”

Shenk was also earning straight A’s as a math major.

“The Collegian was really where I learned to make crossword puzzles,” he said. At first he was breaking all the rules, but by the time he graduated, “they were real puzzles.”

Shenk graduated with a bachelor of science degree in 1979 and began teaching at York County Area Vocational-Technical School, now York County School of Technology. It was a short-lived career that he found “was no fun at all.”

That’s when he decided to send submissions to Games in his free time.

Shortz remembers how impressed he was with those puzzles. “They were so far above most other submissions I was getting,” he said. “He does everything. He comes up with clever puzzle themes. He does whistle-clean grids with colorful vocabulary. And then his cluing is precise and interesting.”

Puzzles as a career

With print publications beginning to decline as the public started using the Internet, the members of the Puzzability team decided in 1996 to follow the trend onto digital platforms. They set up shop for what they hoped would be a growing market for online puzzles.

Nearly 20 years later, their intent of creating an interactive base for puzzlers hasn’t taken off.

Instead, their company has found its niche in puzzles on paper.

“We did think that everything was going to be moving onto online,” Shenk said. “Certainly, a lot of other things have, but puzzles haven’t really moved as fast as we thought they would.”

The partners thought advertisers and online sites like Amazon would offer interactive puzzles and games to draw in an audience. Instead, they found these sites were attracting a strong clientele without entertainment.

Shenk said it wasn’t all that surprising that “a lot of solvers still prefer their puzzles on paper.” He thinks it “feels more natural,” more satisfying. “It feels like you’re filling in the grid, not the computer doing it,” he said.

Shortz, who has accumulated one of the largest online puzzle subscription readerships in the country at The Times, concurs with his protégé’s assessment.

“Crosswords are ideally suited for the print medium,” he said, citing the aesthetics of solving a puzzle by hand and dismissing a computer as inefficient. “That being said,” Shortz added, “crosswords are making the jump to digital media.”

Goldstein, the Puzzability webmaster, oversees the online content of the company. While she has seen a mediocre audience for Puzzability’s interactive puzzles, she said the challenge is figuring out how to expand the crosswords into the evolving world.

“Sure, I worry about it as more and more sophisticated ways of solving electronically” emerge, she said. “I feel like we’re all waiting around to see whether things are going to disappear.”

Shenk said at one point he tried to develop an app for Puzzability, but that idea is on hold.

Instead, he said he is focused on perfecting his print puzzles for Puzzability and for The Wall Street Journal, which made him its puzzle editor and puzzle constructor in 1998.

Shenk’s work can be found online and in print throughout the week, sometimes under pseudonyms. He explains that when the credit for a puzzle said it was created by Mike Shenk and was edited by Mike Shenk, it looks strange.

Sometimes, he creates anagrams out of words and phrases to come up with his pseudonyms.
For an October puzzle, he listed the pseudonym Colin Gale.

“It’s a tribute to where I got my puzzle start,” he hinted. “The Collegian.”

Working, letter by letter

A stream of words rapidly moves down the screen as Shenk scrolls through his word list, a compilation of crossword answers arranged alphabetically.

He is searching for a word to plug into the grid of a Wall Street Journal puzzle.

Shenk is seeking a word that will fit within seven lights, the white cells of the puzzle, and contains the letter 'd’ in the third cell.

“Ardmore, bedsore, odds are,” he reads. “It’s just this long list of words and phrases.”

Long, as in 390,000 entries.

“I can look to see what’s in my list and try to pick one that’s the most lively,” he said.

Shenk said the key to constructing a great puzzle to challenge its solvers but not to frustrate them.

“The best way to put it is that it’s sort of a competition between the puzzle writer and the solver, but the puzzle writer wants the solver to win,” he said. If the solver doesn’t solve the puzzle, he said, the puzzle is not successful.

Shenk is admired in the puzzle world for his clues full of puns, fresh puzzle constructions and, most importantly, for his appreciation of authentic puzzle-making.

The shift from print to digital is evident in the construction phase of the puzzle world.

Acknowledging Shenk at work across the office, Goldstein said: “Almost everybody else uses software except him.”

Shenk himself noted that “there’s been a big move to a lot of people using software.” He said, however, that he uses software as an aid but not to fill in his grid. He hand-selects each word, theme and clue.

When creating a new crossword puzzle, he begins by developing a theme. It can be an approaching holiday, or a catchy phrase or any number of ideas.

He then constructs a digital grid by placing the white and black cells to his liking. He allows space for a variety of short and long words.

Shenk then fills in the cells with solution words. Next he devises clues that are a witty or serious, depending on the word.

“I have moved from doing it on paper to doing it on my computer,” he said, “but I’m still doing it the way I used to do it, which is putting my theme in and guessing where I want the black squares and picking one word at a time.” The task takes anywhere from three to six hours.

Not only does he use software in his grid construction, but he also creates programs. To aid in his puzzle designs, Shenk taught himself Java and Mac coding to write programs that set grids for the crosswords and also for acrostics, which is a game that involves fashioning words from letters in other words.

“If you know acrostics — you find a quote, you take all those letters and jumble them into a set of words — there’s so much bookkeeping involved that you wouldn’t want to try to do that on paper,” Shenk said. “It used to be people would make acrostics with lots and lots of scrabble tiles.”

Like Shenk, Shortz acknowledges the changes in crossword construction. Also like Shenk, he considers software to be an aid, not a “cheat method.”

“Computer systems don’t mean that you push a button and a computer makes the puzzle for you. It can do that, but it’s not going to be a good puzzle,” Shortz said. “Something for The New York Times and The Wall Street Journal requires human involvement.”

While computer programs can suggest clues and words that fit into cells, the creator can alter these for difficulty, cleverness and originality, Shortz said.

“Only a human knows what is an interesting answer or not,” he said. “Only a human can write an original clue. Even with heavy computer involvement nowadays, and most constructors do use the systems, there is still a very large human element in every puzzle,” Shortz said.

Shenk, for example, relies on hand-drawn sketches for specialty puzzles, including the Saturday “Labyrinth” puzzle, a maze-like variation of the original crossword.

Shenk also strays from standard crosswords to invent his own types of puzzles.

He holds up a page-a-day calendar, published by Workman, which is filled with Puzzability’s work.
“We do the whole thing here,” he said, flipping through the pages.

“In fact, Mike wrote most of those puzzles,” Goldstein said. She calls Shenk “the master of the variety puzzles.”

She said Shenk had invented some different types of puzzles, including a framed, maze-like graphic on the desk of the third Puzzability partner, Robert Leighton. Shenk created the puzzle as a gift to Leighton.

Shenk’s creation, called the “The Marching Band,” was inspired by an Italian puzzle. It weaves Leighton’s name and personal phrases through the rows.

“Mike’s crosswords are really good, but these are special,” Goldstein said.

Shenk said he is always looking for new challenges.

“When you make enough crosswords,” Shenk said, “you start saying, ‘Well, what if the grid went in a different direction?’ ”

After creating nearly 10,000 puzzles in his lifetime, who could blame him?

Media Contacts: 
Last Updated January 12, 2015