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The Puzzler:

One Man's Quest to Solve the Most Baffling Puzzles Ever, from Crosswords to Jigsaws to the Meaning of Life

by A.J. Jacobs

After finishing this book in May of 2023, I wrote,


"I read this book more out of curiosity of learning about something that I am not normally curious about and I am glad I did."

My clippings below collapse a 479-page book into 4 pages, measured by using 12-point type in Microsoft Word." 

See all my book recommendations.  

Here are the selections I made (many were truncated because of going over the limit):

The Puzzler: One Man's Quest to Solve the Most Baffling Puzzles Ever, from Crosswords to Jigsaws to the Meaning of Life


 A.J. Jacobs


I learned the surprising history of puzzles, perhaps the oldest form of entertainment. I learned how they’ve played a part in religion, love, and war. How the British secret service used a crossword puzzle in The Daily Telegraph to recruit codebreakers against the Nazis.


I’ve seen the dark side of puzzles, how they can overlap with paranoia and obsession. And I grew to love types of puzzles that never appealed to me before. I talked to scientists about why we’re so drawn to puzzles, why an estimated 50 million people do crosswords every day and more than 450 million Rubik’s Cubes have been sold.


Puzzles can teach us lessons about fresh perspectives, compassion, and cooperation. If we see the world as a series of puzzles instead of a series of battles, we will come up with more and better solutions, and we need solutions more than ever.


Within these pages, I have included my favorite puzzles from history. Why just read about the first-ever crossword puzzle from 1913, when you can solve it?


As I mentioned: devious. I ask Peter why he thinks people—he, I, and millions of others—are so addicted to crosswords. “Well, life is a puzzle,” he says. “Who should you marry? That’s a puzzle. What job should you take? That’s a puzzle. With those puzzles, it’s hard to know if you got the best answer. But with crosswords, there is one correct answer. So that’s comforting.” I nod: puzzles provide a level of certainty you don’t get in this confusing real world. It’s a solid theory, though not the only one, as I’ll discuss next chapter.


During our meeting, Peter told me one of the keys to solving crosswords is to keep your mind flexible. Keep it open to new perspectives. Don’t fall in love with your hypothesis. Good advice for both life and puzzles.


This is another absolutely key strategy Peter and I discussed. When stuck, take a break. Let the problem marinate in the back corner of your brain. Loosen your grip. Puzzle fan Leonardo da Vinci knew this long ago. As he said about painting, “Every now and then go away, have a little relaxation, for when you come back to your work your judgment will be surer.”


I see erasers as a guiding symbol for my life: Embrace the Way of the Eraser. As the saying goes, “Everyone makes mistakes. That’s why there is an eraser on the end of every pencil”


The Way of the Eraser is about being okay with mistakes, okay with tentative beliefs, okay with flexibility. I could be wrong, of course, but I believe that my years of crossword solving have made me more flexible in every part of my life, from parenting to writing to marriage.


As the great philosopher Bertrand Russell said, certitude is a dangerous thing. “The fundamental cause of the trouble is that in the modern world the stupid are cocksure while the intelligent are full of doubt.”


I even talk in probabilities. “When will you be home?” Julie will text me. “There’s a 70 percent chance I’ll be home at 6:30 p.m.”


According to this theory, every morning you should spend two minutes giving your spouse your full and complete attention. Look deeply into their eyes, ask how they are, and really listen to the answer. Then, after work, do the same thing for three minutes. And finally, two minutes before bed. Seven minutes a day, and—voilà!—a lifetime of matrimonial bliss.


I fall asleep by going through the alphabet, thinking of something to be grateful for with each letter from A to Z (A is for the apple pancakes my son made us, and so on).


Constraints lead to creativity. As Orson Welles said, “The enemy of art is the absence of limitations.”


“When you’re doing a jigsaw puzzle, there is one right answer. I find that comforting…Virtually every other aspect of the world is in shades of gray.” She quotes an article she once read: “A jigsaw puzzle won’t solve all your problems, but it’s a problem you can solve.”


I think of Barack Obama’s dream of opening a T-shirt shop. He once said he was so sick of hard decisions that he fantasized about opening a T-shirt shop on the beach that sold only one item: a plain white T-shirt, size medium. Freedom from choice. Several years ago, I wrote a book in which I followed all the rules of the Bible, and even though I’m not religious, I saw the appeal of a highly structured life. The freedom to choose has many benefits, but in certain circumstances, so do strict limitations.


But I love the blue-eyed problem for another reason. It’s a crash course in perspective-taking, in seeing the world from someone else’s point of view. Which to me is an absolutely crucial skill, especially in these times of heightened tribalism.


A Fermi problem is one like this: “How many piano tuners are there in New York City?” You have to estimate the size of something about which you are totally ignorant.


As Epstein writes: “How many households are in New York? What portion might have pianos? How often are pianos tuned? How long might it take to tune a piano? How many homes can one tuner reach in a day? How many days a year does a tuner work?” You won’t guess it exactly, but you’ll be much more likely to be in the ballpark. As Epstein writes, “None of the individual estimates has to be particularly accurate in order to get a reasonable overall answer.”


A British journalist devoted an entire book to the phenomenon called The Quest for the Golden Hare, and he writes:


“Tens of thousands of letters from Masqueraders have convinced me that the human mind has an equal capacity for pattern-matching and self-deception. While some addicts were busy cooking the riddle, others were more single-mindedly continuing their own pursuit of the hare quite regardless of the news that it had been found. Their own theories had come to seem so convincing that no exterior evidence could refute them.”


Our mental frames change the way we interpret the world. And that’s why I think these optical illusions are such powerful metaphors for life. I’ve come to believe in the importance of frames and reframing. As with the vase and the face, there are often different ways to interpret the same situation.


I tell him that such stories make me nervous for the future in the face of advances in AI. Garry shakes his head. “I’m more optimistic about the future of humanity,” he says. “You’re not worried about AI taking over?” “Why should I be? I was the first knowledge worker whose job was threatened by machines,” he says. I laugh. It’s true. In 1997, Garry was famously beaten in a chess match by IBM’s supercomputer Deep Blue. “I think it’s wrong to cry about progress,” he says. “The future is not humans fighting machines. The future is humans collaborating with machines. Every technology in history destroyed jobs, but it also created new ones.”


Recently, I was watching a webinar from a child psychologist. The topic was something like “a parent’s guide to surviving quarantine,” and I figured I could use all the help I could get. During the webinar, the psychologist gave the following advice: “Don’t get furious. Get curious.”


The author and podcaster Julia Galef talks about the scout mindset versus the soldier mindset. Scouts explore the intellectual terrain looking for truth, for information that counters their biases, for evidence one way or the other. Soldiers, on the other hand, are looking to win the intellectual battle by any means necessary. They are looking to confirm their biases using motivated reasoning.


Psychologist Adam Grant uses a different schema in his bestseller Think Again. He categorizes thinkers into scientists, preachers, prosecutors, and politicians. Only one of them, the scientist, is open to changing her mind; the others are using motivated reasoning.


He says we need to think more like engineers and less like lawyers, because engineers look for solutions, while lawyers look for evidence that reinforces their side.


We could all use more curiosity, one of the greatest human virtues. I once interviewed the late Jeopardy! host Alex Trebek for a magazine article, and he told me something I think of often. He said, “I’m curious about everything—even those things that don’t interest me.” It’s a bit paradoxical, perhaps even nonsensical. But I think it’d be a better world if everyone was more like Alex. ABC: Always be curious.

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