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

Red Tape Disease

Dutch elm disease is one of the world's most serious tree diseases. It is caused by the fungus Ophiostoma novo-ulmi, which invades and blocks the water-conducting systems of trees. This results in the wilting and death of the tree.

* * * 

Imagine you've bought a home in the heart of a bustling city. You diligently pay your property taxes, mortgage, and insurance. You enjoy your home because it is yours. 

But there's a catch. If you decide to renovate, to modify this home to make it correspond to your vision for the home, you must first navigate through a maze of city regulations just to get the green light. You're then obligated to hire contractors who are on the city's approved list. After all this, a city inspector shows up to scrutinize every detail of the work done. This scenario hardly screams freedom. Instead, it highlights how even the fundamental right to control your own property is tightly regulated by government oversight. You're tangled in red tape.

Nationally we have a housing crisis not because of a lack of builders, but because nearly every city and state is strangled by red tape. Locally, I met a contractor who said, "I will never build another house in Duluth." Why did he say this? Because it takes so long to get a permit. He said that it took him six months to get a permit to raise someone's garage floor by two feet. "In Hermantown it would have taken 24 hours." 

I read last week that for the unfortunate victims of L.A.'s recent fires, people who lost their homes must file with 14 or 16 different agencies to get approvals to rebuild.

When I spoke to an official in Duluth about why it takes so long to get permits, he said it has to go to the State for approvals also. (This doesn't answer the question as to why Hermantown's building projects can move more quickly than Duluth's.)

If you want to build a factory here in Northern Minnesota (because Midwesterners have strong work ethic) you must not only deal with local, county and state regulators, but also many federal agencies. I've seen multi-million dollar projects get approvals all along the line but shut down by one more agency along the way. One project that would have generated more than 40 new jobs was shut down because an opponent found an endangered species of weed.

Here's an excerpt from a New York Times story I saw yesterday:

Consider clean-energy projects. These are meant to create jobs — in solar, wind, nuclear and so on — and combat climate change. But passing a law that spends money on such projects is only the first step. The companies and agencies involved have to apply for permits and show they meet regulatory standards to start construction. The government takes time to assess those applications.

The process can last months or years before building begins. More than two years after Congress enacted $5 billion to electric vehicle charging stations, just two states — Ohio and New York — had opened any. After three years, the number of stations nationwide numbered in the mere dozens, out of thousands the program could eventually build.

German Lopez, Cutting Red Tape, NYTimes, The Morning, Feb 17, 2025

Our energy demand is growing faster than our energy supply. One reason is because energy suppliers are hamstrung by red tape. Projects that should take less than eight years can take sixteen because of all the regulations and hurdles energy suppliers must navigate. 

Is the red tape industry out of control? Is red tape our economy's Achilles Heel? Is Red Tape our Dutch Elm Disease?

Is the U.S. Media a Mouthpiece for the State? Stephen Kinzer Argues "Yes"

Those of us who grew up during the Cold War were constantly reminded that Pravda, the state news vehicle of the Soviet Union, was primarily a channel for Soviet propaganda.  The word pravda means truth and its primary function was to spread the Party's message to the rest of the world.

The unspoken message here was that our media was the voice of the good guys and that it was not propaganda. It was a free press reporting real news as it happens.

A couple nights ago I was listening to an interview with Stephen Kinzer on National Public Radio. Kinzer is a journalist and author who was formerly with the New York Times. On NPR Kinzer stated that he and the Times parted ways over the issue of journalistic integrity, especially with regard to being a channel for the U.S. propaganda. (This was how interpreted what he said on the air.)

As one who has written about this topic on numerous occasions (eg. He Who Controls the Narrative Controls the People, and The Purpose of Propaganda: Social Engineering) it made me interested in learning more about Stephen Kinzer, his ideas and experiences, so I asked Google Bard for a summary of Mr. Kinzer's views on the U.S. media as a mouthpiece for our government and the Pentagon.*

Bard Replied:

Stephen Kinzer is a journalist and author who has written extensively about the role of the U.S. media in foreign policy. He argues that the U.S. media has a long history of serving as a mouthpiece for the government and the Pentagon.

Kinzer points to several examples of this, including:

• The media's uncritical reporting of the lead-up to the Iraq War, which was based on false claims about Iraqi weapons of mass destruction.
• The media's failure to challenge the Bush administration's justification for the war in Afghanistan, which was based on the claim that the Taliban was harboring al-Qaeda.
• The media's reluctance to report on the human cost of U.S. wars, such as the war in Iraq, which has killed hundreds of thousands of civilians.

Kinzer argues that the U.S. media is not simply passive in its role as a mouthpiece for the government. He believes that the media is actively complicit in promoting U.S. foreign policy interests. (EdNote: emphasis mine) He cites the example of the media's coverage of the Arab Spring, which he argues was largely supportive of U.S. intervention in the region.

Kinzer's views on the U.S. media have been controversial. Some critics have accused him of being too critical of the media, while others have said that he is right to point out the media's biases.

* * *

This is exactly what Seymour Hersh was shocked to find when he came to D.C. to be part of the Washington Press Corp. DC journalists enjoyed hobnobbing with the government elite. As a result they became bedfellows and were reluctant to be real reporters.

Hersh began ruffling the status quo with stories like his unearthing the My Lai massacre and by tracking down Lt. Calley, the Viet Nam War atrocity scapegoat. (Recommended: Reporter by Seymour Hersh is a Must Read for All Young Journalists)

Regardless of one's views on Kinzer's specific arguments, there is no doubt that the U.S. media plays a significant role in shaping public opinion about foreign policy. Many believe Kinzer's work has helped to raise awareness of the ways in which the media can be used to promote government interests. 

* It should be noted that AI systems are sometimes unreliable. The Bard's views seemed like a fair description to me.

Woodstock Story in a Bottle: Another Defining Moment of 1969

Insignia that appeared on Yasgur Farms milk bottles.

That summer two men walked on the moon. And in August 400,000 people saw stars.

Just as a good movie is made of memorable scenes, so history is remembered by its defining moments. For Americans, the year "1968" brings Viet Nam, assassinations (Bobby, MLK, Jr), and riots to mind

In 1969, two very different images were impressed upon us, that "one giant leap" for mankind and that escapist utopian dream, Woodstock.  (It's convenient to keep Altamont off-camera when we want to feel good about this Woodstock music and love experience as a culmination of the Sixties.)

There were many ironic features of the event, one being this one: the song we've all associated with it, "By the time we got to Woodstock," was penned by someone who wasn't event there. Joni Mitchell was in New York City to be on TV that weekend.

Here's a second irony. As every Dylan fan knows, Woodstock's most famous resident-in-hibernation, who many considered the hippest cat on earth, was packing his bags to head to England for an Isle of Wight concert.

* * * *
I'm going down to Yasgur's Farm
Gonna join in a rock and roll band
Got to get back to the land and set my soul free

Yasgur's farm was actually 43 miles Southwest of Woodstock, in Bethel NY.
Photo courtesy Bill Pagel.

How many farmers can you think of, besides Old MacDonald, have been memorialized in song? Here's an excerpt from his Wikipedia account, by way of introduction.

Max Yasgur was born in New York City to Russian Jewish immigrants Samuel and Bella Yasgur. He was raised with his brother Isidore (1926-2010) on the family's farm (where his parents also ran a small hotel) and attended New York University, studying real estate law. By the late 1960s, he was the largest milk producer in Sullivan County, New York. His farm had 650 cows, mostly Guernseys. 

Though Yasgur was a conservative Republican, his conscience also told him that older folks need to do something to bridge the generation gap. He was motivated by his principles and did not yield to those who were pressuring him to call off the festival.

* * * *

When I saw this bottle from Yasgur's farm, I couldn't help but think of the Old Testament Psalm 56:8 in which the psalmist/poet writes, "You put my tears in Your bottle." I think of all the tears that were shed during the 60s, from JFK to all the grief and sadness caused by Viet Nam. And sadly, worse was yet to come.

My next thought was even stranger. What were bottles like 3,000 years ago? King David wrote this song when he was captured by the Philistines. Whatever shape they took, for the psalmist it was not a time of music and celebration.

* * * *

Photo by Francisco Moreno on Unsplash

Woodstock took place from August 15 to 18, 1969. The performers most of us remember most were the ones on the album and the film. Some were excluded due to contract issues.

Here are some stories that go deeper and provide more perspective than I have time to produce. If you have time, check them out.

A New York Times account of one of the iconic photos.
https://www.nytimes.com/2019/08/08/arts/music/woodstock-famous-couple.html

A good summing up of Woodstock by the NYTimes
https://www.nytimes.com/2019/08/05/arts/music/woodstock-50-anniversary.html

Rolling Stone interview with Bob Weir, who was shocked. (Literally)
https://www.rollingstone.com/music/music-features/woodstock-grateful-dead-bob-weir-855472/

Time Magazine published this review of the latest Woodstock documentary
https://time.com/5638166/woodstock-pbs-generation-review/

Here were a couple thought-provoking paragraphs from the above.

For those who were coldbloodedly watching numbers, even in 1969, Woodstock simply identified a big, promising segment of the youth market, ready for the commercial exploitation that would ensue almost immediately. “Woodstock Nation,” despite Abbie Hoffman’s hopes when he coined the term, turned out to be a demographic rather than a political force.

This one is also barbed.

But forget the nostalgia. Millennials have every right to point out how Woodstock represented baby boomer privilege in crystalline form. We got a free marathon all-star concert. (I don’t begrudge my $18.) We swarmed a previously unspoiled dairy farm and its surroundings. We absolutely thought we were the center of the universe. And afterward, someone else had to clean up the giant mess we left behind. Insert the global-warming analogy.

You can insert a number of alternative messes here.

Were you there? What was your story?

Related Links
For Carlos Santana, Woodstock was a Trip
https://www.nytimes.com/2019/08/06/arts/music/santana-woodstock.html
Surviving Woodstock, a New Yorker story by Hua Hsu
https://www.newyorker.com/magazine/2019/08/05/surviving-woodstock