Outer Richmond Math Teacher Enjoys Creating Crossword Puzzles

By Erin Bank

In 2020, the nonprofit Jess Goldstein worked for cut back its operations due to the COVID-19 pandemic. In her newfound spare time, Goldstein revisited an old hobby: creating crossword puzzles.

“I always loved them,” Goldstein said. She remembers solving them as a kid, growing up in Minneapolis, and then trying to create her own by taking words and making them cross each other, like a Scrabble board. 

Goldstein continued solving puzzles as an adult and found a group of colleagues at work who would solve the daily puzzle in The Atlantic. After her job ended, Goldstein said she poured everything into constructing her own puzzles. 

“It was on my list of things to do before I turned 30: publish a crossword puzzle,” she said. 

She began not knowing anything about how to even start making a puzzle. As a solver, she was already familiar with the various conventions and norms that appear in most puzzles. For example, if there is an abbreviation in the clue, there will be an abbreviation in the answer. But to construct her own, she consulted how-to guides online and learned as she went. 

Now, her process is to go to her Outer Richmond roof deck and brainstorm on a theme. For example, she came up with the idea to construct a puzzle based on a theme of the card game Uno (the puzzle was published online for The New York Times in October 2020). She made a list of phrases that began with the Uno cards Skip, Draw, Reverse and Wild. She picked the four phrases she liked best and entered them into a blank 15×15 grid. Then, she filled in the black spaces to make a symmetrical pattern (the norm is that an empty puzzle can be rotated and has the same pattern no matter which way is up). She then consulted her word list, dictionaries and her own knowledge to fill in the words that comprised the rest of the puzzle.

Finally, it was time for her favorite part: making the clues.

“I was so surprised to learn that the clues come last,” she said. Many editors don’t ask for the clues until after they’ve reviewed the filled-in grid to make a decision regarding publication.

Goldstein began sending her puzzles to family and friends to solve, and then started a blog where she could attract a wider audience. 

Goldstein has found a strong community of constructors, who she said is over-the-top welcoming and nice, even as the community has grown in recent years.

“Everyone cheers each other on,” she said. 

She cold-called one of the constructors she admired, Olivia Mitra Framke and their correspondence led to a collaboration on a puzzle, which was published in USA Today in April 2021.

Goldstein is now a math specialist at a school in the Richmond District. She still takes creative time in the evenings to work on a puzzle, as a respite and change of pace from her job.

As she has gotten better, Goldstein said she has more of a discerning taste when it comes to her own puzzles. Sometimes that means they take her longer to construct, but she knows the end result is a puzzle that her solvers will feel satisfied completing. Goldstein’s goal is to make sure every word in her puzzles has a reason for being there. She laughed about filler words and how many times the hockey player Bobby ORR appears in puzzles, and how everything with a round shape is an ORB.

Constructing more diverse, modern puzzles is a trend across the crossword world. The vast majority of puzzle constructors – and the editors who publish them – are white men. This helps to explain the predominance of sports, opera, and obscure (i.e., old) cultural references. One of Goldstein’s favorite series of puzzles is that put out by The Inkubator, who publishes “crossword puzzles by women — cis women, trans women and woman-aligned constructors.

“Representation matters,” she said, explaining how it’s just not satisfying as a solver to have to look up answers,  or realize puzzles are not written with their perspective in mind. It is the difference between using a lyric from Lizzo or a lyric from the Beatles; a reference to a women’s basketball team rather than a male’s.

Goldstein said that more outlets are publishing puzzles, in more niche areas like cycling magazines. She hopes this will allow constructors to create puzzles in areas of personal interest and that are more representative of the solvers.

To see Jess Goldstein’s first crossword puzzle exclusively for the Richmond Review, click HERE.

See more of Jess Goldstein’s crossword puzzles on her blog,

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