After meeting Andrea this summer, I understood exactly what Christina meant. Coming of age in Minneapolis, Andrea Carla Michaels has lived a life as dynamic and engaging as the crossword puzzles she’s famous for crafting.
From her early days as a chess prodigy and puzzle enthusiast to earning a psychology degree from Harvard at age 20, Andrea’s path has been anything but linear. She’s performed stand-up comedy in Los Angeles, written for TV shows like Designing Women, won a motorhome on Wheel of Fortune, and become a nationally ranked Scrabble player. In San Francisco, she founded Acme Naming, a corporate naming consultancy, and earned the title “Queen of Mondays” for her 85+ accessible, playful crossword puzzles published in The New York Times. Her contributions to the crossword world recently earned her the prestigious 2024 Merl Reagle MEmoRiaL Award, an annual honor presented at the American Crossword Puzzle Tournament.
Yet Andrea’s impact extends far beyond her creative achievements. Known in San Francisco as the “Pizza Lady,” she’s been distributing food and clothing to the homeless since 2015, expanding her efforts during the COVID-19 pandemic and even reuniting lost luggage with its owners. Her advocacy for rent control and community service earned her a 2023 certificate of honor from the San Francisco Board of Supervisors.
In this interview, Andrea shares insights from her atypical life journey—spanning comedy, crosswords, corporate naming, and philanthropy—revealing how her love for words and people has shaped a life of purpose and play.
Ennyman: Growing up in Minneapolis, you developed a love for puzzles and games, even competing in chess championships as a young girl. How did your early experiences in Minnesota shape your creative and problem-solving skills? Did this all play a role in your later career as a crossword constructor?
Andrea Michaels: Minnesota influenced my career in two ways… We had moved there from Florida. I was in shock so stayed inside and read and did puzzles. But I think I got my naming start looking at the sailboats names on Lake Harriet.
I wrote a paper in 10th or 11th grade asking if people liked their name or would like to change it or if they knew what their name meant and on and on!
EN: You studied psychology at Harvard? Your later work in comedy seems like quite a pivot. How did your academic background influence your diverse career path, and are there specific skills from your studies that you apply to your creative or professional work?
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| Talking with Will Shortz, NYTimes Games Editor |
Generally I just like a great story! [I went to] Harvard just becauce I was a very precocious little girl and learned quickly and wanted to go somewhere that no matter what course I chose (at school/in life) that chances are they’d have a good department in it! I was interested in everything and quite the dabbler /dilettante!
EN: You’ve had a varied career, from performing stand-up comedy in Los Angeles to writing for TV shows like Designing Women and appearing on game shows like Wheel of Fortune and Jeopardy!. What drew you to these entertainment ventures, and how did those experiences lead you to settle in San Francisco and focus on crossword construction and corporate naming?
AM: It’s all connected. It’s all writing and playing with words. Zero grand plan.
I fell into standup as I like to tell stories and friends encouraged me to do it on stage.
I love Gameshows and thought money was silly and you might as well just win it.
That led to writing for game shows. And as I was doing standup that led naturally into sitcom writing.
I didn’t like LA though and didn’t really watch sitcoms. Didn’t like driving. Longed for San Francisco so I moved back there. Had a friend in branding who’d asked me to help her name things. I asked if I could sit in a corner and name stuff.
Each thing has led to the next. Always solved crosswords and liked trivia so that led to writing them just for fun now and then.
The big goal was not to work too much. To have a different creative adventure every day. No one asked me to do any of the things I do. I just want everything to be fun.
I lost on jeopardy! Army captain set a record on my show and the final question was on the civil war. :(
EN: More recently you have been labelled or titled or crowned the “Queen of Mondays” for your New York Times crossword puzzles. You’re known for creating accessible yet lively puzzles. Can you walk us through your creative process for designing a crossword, and what makes a Monday puzzle distinct in terms of challenge and appeal?
I also like rhymes and even rap (when not profane or misogynistic) as I like to hear how folks play with words. I never consciously set about to create a puzzle. I’ll just hear something or notice some fun gentle word play and think it might make a cute puzzle.
But then I have to sit down and be conscious of matching word lengths and all the mechanics of a grid which interests me not! (Which is where your lovely daughter* comes in! She actually enjoys that part which is why I now collaborate all the time.
I like helping others' ideas come to fruition by being “worked out” and then if they LIKE making grids… then yay!) Then I’ll clue just to make sure it is clear and light and hopefully bouncy.
I never specifically think I’m making a “Monday” but that’s just where my ideas fall on the spectrum. They were never meant to be easy or “gateway” puzzles but have been so assigned which is fine but I never intentionally dumb anything down or whatever… I’m just practiced in making them “accessible.” Unlike many creators, I’m never ever trying to stump anyone or be tricky. I’m trying to bring a little smile or trigger a fun memory or say, “Look! Have you ever noticed this!”
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