Will Shortz, NY Times Crossword Puzzle Editor
Today, my guest is Will Shortz (aka the "Puzzle Master"), Editor of the New York Times Crossword Puzzles, and star of WordPlay (see trailer below), one of my favorite movies.
Some may know that he graduated from the University of Virginia Law School but probably not many know that he almost dropped out after his first semester and that his favorite class was intellectual property!
Listed as one of the 30 most famous people with law degrees, Will was gracious enough to join me for this conversation about his law school days from his home in Pleasantville, New York.
In this candid conversation, Will shared the real stories behind his unusual path through law school, his love for tests, and his lifelong dedication to puzzles.
1. The Puzzle Major and the LSAT. Will revealed that his undergraduate major at Indiana University was actually in puzzles, and his deep passion for wordplay made him love taking the LSAT. When he took the exam, it featured an experimental wordplay section that he absolutely "ate up," and he later told the LSAT creators at their annual convention that he genuinely enjoyed taking the test—to which they replied he was likely the only person to ever feel that way.
2. Law School as Puzzle Training. Despite not wanting to become a practicing attorney, Will found that his time at the University of Virginia School of Law provided excellent training for a career in puzzles and business. He explained that studying law teaches you how to take a complex issue, separate the threads, and deal with each part individually, which is exactly the analytical process required to solve a difficult puzzle. Beyond the coursework, he simply loved the intellectual challenge of being tested and even helped lead the law school's softball team to its very first championship.
3. The "Penny, Press" Law Firm. During his third year of law school, Will's guidance counselor called him in, highly concerned because he was the only student in his class who had never interviewed for a single job. When he told her he already had a job lined up with "Penny Press," she visibly brightened to help her statistics and wrote it down on her form, mistakenly waiting for the rest of what she assumed was a law firm's name. In reality, Will had been working at the puzzle company during his summers and went back full-time after graduation before eventually moving on to Games Magazine.
4. Choosing Fun Over Law. When asked if he ever felt curious about actually practicing law after spending three years and a lot of money on his degree, Will admitted he had absolutely no desire to try it. Aside from his overwhelming love for puzzles, he noted that he generally found lawyers to be humorless people. Ultimately, he much preferred his creative career path because it naturally suited his personality and allowed him to laugh a lot and have fun at work.
