Unlocking the Art of Puzzle Creation

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A.J. Jacobs (@ajjacobs) is a bestselling author, journalist, and human guinea pig. He has written four New York Times bestsellers, including The Year of Living Biblically (for which he followed all the rules of the Bible as literally as possible) and Thanks a Thousand (for which he went around the world and thanked every person who had even the smallest role in making his morning cup of coffee possible). He has given four TED talks with a combined 10M+ views. He contributes to NPR and The New York Times and wrote the article “My Outsourced Life,” which was featured in The 4-Hour Workweek. He was once the answer to one down in The New York Times crossword puzzle. You can find my 2016 interview with A.J. at tim.blog/aj. 

His new book is The Puzzler: One Man’s Quest to Solve the Most Baffling Puzzles Ever, from Crosswords to Jigsaws to the Meaning of Life.

Please enjoy!

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Why have A.J.’s kids lately deigned to show him a modicum of respect? [06:20]

For most of his books, A.J. has a number of friends read the draft and offer suggestions for edits — what to cut and what to keep. Why was this usually sound strategy a bust for The Puzzler? [07:15]

Why did A.J. abandon his next planned book midway and pivot to writing The Puzzler? [08:54]

Is A.J. more of a George Plimpton or a Nellie Bly? [11:18]

Why puzzles are worthwhile and not, as I once believed, frivolous time-wasters, and what happened when A.J. discovered he was a clue in the world-famous New York Times‘ crossword puzzle. [14:42]

How does one compete in the World Jigsaw Puzzle Championship? For that matter, how does someone who doesn’t really even like jigsaw puzzles wind up representing their whole country in one? What did A.J. and his hastily assembled Team USA learn about jigsaw diplomacy and strategy when they unwittingly became participants in this annual event? [17:25]

What would “the Ironman triathlon for nerds” look like? A.J. reckons it would be something like an MIT puzzlehunt. [23:25]

“Don’t get furious. Get curious.” Every problem or disagreement is just a puzzle in search of a solution. [24:08]

A.J.’s writing process is strong on structure and outlining, but he likes to allow room for surprises. One of these surprises while penning The Puzzler: a decades-unsolved CIA puzzle sculpture called Kryptos. [28:41]

On puzzle trolls, fabulous prizes, and what you can win if you solve one of A.J.’s designated puzzles in The Puzzler. [32:38]

What makes a good puzzler (and why does A.J. consider himself a better puzzle solver than puzzle creator)? As an aside: A.J. shares the origin of the phrase “Think outside the box.” [33:50]

Transferable ways we can apply our puzzle-solving skills to other areas, with examples from a preteen Gauss, British crosswords, tormenting jigsaw puzzles, and reverse-thought riddles. [38:39]

What puzzles does A.J. consider to give the most bang for their buck? It all depends on what you’re hoping to retain from the act of doing them, but Japanese puzzle boxes take things to a whole new level. [51:04]

The shadow side of puzzles that drive people mad: the Monty Hall problem, the Sleeping Beauty problem, and a puzzle A.J. commissioned that can’t be solved within the lifespan of the universe. [54:41]

If researching and writing Thanks a Thousand imparted A.J. with a lifelong appreciation for gratitude, what residual takeaways from writing The Puzzler does A.J. predict will remain with him for years to come? [1:00:26]

In what puzzle-oriented subculture would A.J. feel most at home? [1:03:08]

Obsessed with puzzles? Beware the perils of apophenia. [1:05:16]

According to A.J., the hardest corn maze in the world is run by a sadist in Vermont. What has this sadist learned about human nature during the time he’s spent observing people trying to escape from this maze? [1:07:40]

On puzzle creation epicenters, Garry Kasparov, and how chess puzzles differ from chess games. [1:10:10]

How do puzzles pertain to the meaning of life? [1:15:06]

Parting thoughts. [1:17:34]

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