Turn Your Passion Into A Career, Like New York Times Puzzle Editor Will Shortz

This is Power of Networks, interviews featuring real-world career advice from leaders at the top of their games.

The New York Times crossword editor Will Shortz is the world’s only academically accredited enigmatologist and a cult hero among puzzlers worldwide. He is the rare case of someone who turned his childhood hobby into a lucrative career. In addition to his role at the Times, Shortz is puzzlemaster at National Public Radio, founder/director of the American Crossword Puzzle Tournament, founder of the World Puzzle Championship and the author or editor of more than 500 puzzle books. He wrote the riddles for the film Batman Forever and has guest-starred in episodes of The Simpsons and How I Met Your Mother. I asked Shortz how he leveraged his interest in games to become an international rock star.

 Jessica Pliska: You are the definition of an unconventional high-powered professional. How did you start?

Will Shortz: Some people see me as a role model for oddballs. I have always loved puzzles. I sold my first one at age 14 to my national Sunday school magazine. At Indiana University, as part of their Individualized Major Program, I created my own major in enigmatology, the study of puzzles.

I dreamed of a career in puzzles as a child, but I thought it was impossible. It was my mom who found the program at IU. I owe a lot to her. My dad didn’t much care for the idea. He always said, “Puzzles are an avocation, not a vocation.” But he eventually came around.

Pliska: I keep hearing a common theme from very successful people: influential people in their lives told them they couldn’t succeed, and it drove them harder.

Shortz: That was true for me as well. In my first meeting with the head of the Individualized Major Program, she explained all the reasons why a major in enigmatology would be difficult. I walked out of her office more determined to do it than when I had walked in.

When I was a kid, I wrote a letter to Dmitri Borgmann, the author of a classic book on wordplay called Language on Vacation, to ask for advice on how to have a career in puzzles. He sent me a three-page, typed, single-spaced letter describing all the ways he could think of to have a career in puzzles—and why none of them would work. I stuck with it anyway.

Pliska: Did you have a backup plan?

Shortz: My original plan was to become a lawyer, make a lot of money, then retire and do puzzles. I earned a law degree from the University of Virginia. But upon graduation, I skipped the bar exam and went right into puzzles.

Pliska: You’ve built a unique brand. How did you parlay the New York Times crossword puzzle into so many other gigs?

Shortz: I say yes to most interviews if I can afford the time. That helps keep me in the public eye, although that isn't exactly why I do them. Being on NPR every week with 3.5 million listeners is valuable because it's a captive audience. Anyone who reads the Times but isn't interested in crosswords will simply turn the page. NPR listeners, though, have to sit through my seven-minute puzzle if they want to get to the next story. In general, I take advantage of opportunities that come up, through relationships with people I know or otherwise. I've never had a planned career arc, but one thing has led to another.

Pliska: How have you built such a dedicated following?

Shortz: I work my hardest, am honest with everyone and try to have a good time myself. I think these positive qualities are apparent to others.

Bringing people together is one of my driving motivations. I've taken what is essentially a solitary activity and made it into a community by hosting puzzle tournaments and events.

To broaden the audience at the Times, I've added more modern references to the puzzles and increased the playfulness of the themes and clues. And I publish many puzzles by young people. I truly believe that crosswords are for everybody.

Pliska: It seems like you have an unmatched career. Do you have competitors?

Shortz: I don’t really think about "competitors." Whatever is good for the puzzle world as a whole is good for me. I'll recognize and promote anyone who does what I think is quality work, including in publications that compete with the Times.

Pliska: Your career trajectory was unusual. What advice can you share that’s useful to young people more broadly?

Shortz: First, connections and relationships matter. I tell young people who are interested in puzzles to attend puzzle tournaments and events. Get out and meet people. That’s how opportunities arise.  Part of the reason I think I got my job at the Times was that I belonged to a monthly lunch group of elderly crossword constructors in New York City. Everyone else was probably 60+. I was around 40 at the time—the only "young" person invited to join. When the Times was looking for a new crossword editor, someone who could bridge the world of older and younger solvers, I was the natural person to ask.

The second thing is to know your field, whatever it is. I once had a summer research grant from Indiana University to study the history of puzzles at the Library of Congress. That's where I found The Enigma, the magazine of the National Puzzler's League, and I read all the issues back to 1903. I also read every puzzle book and article there that I could get my hands on. I became a regular contributor to Dell puzzle magazines when I was 16 and never stopped making puzzles thereafter. So I think I understand the history, psychology and nuts-and-bolts of my field better than anyone else.

Finally, having a mentor helps, if you can find one.

I tell everyone how important it is to love what you do. A good field is one in which you don't mind even the least interesting part of your job. I love everything about what I do, even the typing. When I hire summer interns for the Times, the most important qualities I look for are intelligence and a love of puzzles.

Pliska: Have you ever been recognized in public while doing a crossword puzzle?

Shortz: It has happened.