Andrea Michaels: An Unconventional Life

When my daughter Christina first mentioned Andrea Michaels, she described a woman whose vibrant, multifaceted life seemed almost too extraordinary to capture in a single story. “She’s really cool, Dad,” Christina said, sparking my curiosity about someone whose journey weaves together wit, words, and a deep commitment to community. 

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?

Talking with Will Shortz, NYTimes Games Editor

AM: These are heavy questions I’ve never thought about. I went there thinking I’d study English and Linguistics but was in over my head in those departments. Certainly psychology has played an enormous part when I taught ESL to Japanese businessman… And every naming client one has to deal with the entirety of their childhood and subjective takes on matters!!!! And that is more an experiment in social/group psychology than stand up!

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?

AM: I think I like to think in terms of catch phrases and idioms from having been an ESL teacher… and it fascinates me how people talk especially when they unconsciously mix metaphors… or talk in cliches.

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!”

 

Related Link

Meet SF’s Pizza Lady: Fighting Waste While Feeding the Hungry

Name Games

I don't know if everyone has as much fun with naming as I do but coming up with names for my paintings and blog posts is something I take a measure of pleasure from. Every couple who's had children has probably wrestled with the problem of coming to agreement regarding the names we choose with our spouses. We may not have a say in our own names, but we certainly want a voice in what our kids will be called growing up. It's one of the privileges of parenthood, isn't it?

We name our pets and sometimes even name our vehicles. Authors name their stories and books, businesses wrestle with naming new products and owners of race horses must get a thrill out of naming their hoped-for future champions. Maybe we ourselves didn't have a say in it but the places we live all have names, both the cities as well as the roads. Stars and combinations of stars have been named, and even our diseases have names.

Yesterday my September Artforum arrived in the mail and as I was paging through the first hundred pages of advertisements for galleries and shows (this edition has near 400 pages again) I was struck by how fascinating or intriguing many of the shows' titles were. Here's a sliver from that list of advertised shows. You can read it like a poem, or you read it as a series of "idea prompts" for a set of essays.

Eighteen Stations
Fly Away
In the Wake
Bare Shouldered Beauty
A Century of Nudes
Line into Color, Color into Line
Jumping Over My Shadow
through patches of corn, wheat and mud
Extensions Made To Trouble Transformation
Facility of Decline
Woman Power
Blockchain Future States
Small Brass Raffle Drum
Some Terrible Problems
Headspace
This Brutal World
On the Other Side of Tomorrow
Really Good
The Guests All Crowded Into the Dining Room
Sanctuary
The Toast is Burning
Three Cats
Waiting for the Barbarians
After Pasteur
Any Fallow Field
serious candy revisited
Remains to Be Seen
Cathedral of the Pines
Silence of the Music
25 years of collaboration
Gathering Clouds
Honor and Disgrace
New Geometries

I find it interesting how the magazine has become so massive, a reflection of the bloated dollar values for serious work in the art market today. The ads feature galleries from New York, Berlin and Hong Kong to Madrid, London and Istanbul. The art scene is a truly international affair.

Locally, I've enjoyed the variety of names our artists come up with for their events and projects. Here's a another list.

From the Basement
Rust & Flow
Fragments/Memory
Getting Real
Busy Being Born
Underwater Dreaming Bunnies
Saturated Life
Land of Wonder
Collection of Chaos
and
Life & Art Entangled

This isn't the first time I thought about names as a blog theme. In July 2009 I made a list of names I'd attached to many of my paintings.

What have you named lately? Do you like coming up with names, or is it simply a necessary evil? For the record half of our geese are named, but the other half are not. It's a tradition here. We prefer not to name the geese designated for devouring.

Meantime life goes on. It's the name of the game.

The Joy of Naming

From the beginning man has named things. Adam and Eve were given authority to name the animals and have been naming things ever since. 

This week a scientist named a new element. Through the centuries we have named stars, planets, plants, diseases, instruments, objects. Artists, too, carry this godlike expression even further – creating poems, pictures, stories, art… so they can enjoy this special privilege: naming.
Journal note, March 19, 1994

Naming is one of those things that can really be fun. Coming up with names for our various pets has created meaningful and memorable experiences in our home. Whether the dogs (Hobo, Gypsy and Jubiliee) or the goats, geese, duck, cat, birds, rat... whatever... Something would be missing if they didn't have names.

I enjoy making art, but I also enjoy the process of naming the pieces half again as much as creating them sometimes. I like writing poems, but also like making a title for each. And for stories as well.

In sifting through an old journal I came across these names or titles for potential stories.
Attention Span
Token Memories
The Hall of Light

I once developed an idea for a Hollywood movie called Pause Button based on the notion "wouldn't it be great if life had a pause button so we could stop time and get everything done that we never have time for?"

Speaking of naming things, think about the significance associated with your own name. How might you be different had you had a different name? Think of all the people who change the name they have been called by when they grow up. And if you are a parent, think of the special care and attention that you gave to naming your own children. Naming is a powerful thing.

On this topic much more can be said, but for now... it's time to move on.

EdNote: This 2007 blog post has been lightly edited from its original form.