Applying Crossword Thinking To The Creative Process

October 25, 2018

I remember solving my first New York Times crossword when I was 11 or 12. I had been practicing a lot, helping my grandma look up answers for her own puzzles and taking several stabs on my own. In pencil, of course. Lots of erasing. When I finished that first puzzle, it was a refrigerator moment. More than 20 years and thousands of puzzles later, my sense of achievement and satisfaction is still sweet upon completing a grid. But I’ve started to question how crosswords have shaped the way I think. And I’ve discovered some good and bad habits I’ve picked up.

Crossword Solving is Great for Work Flow

Solving crosswords flows quite similarly to solving creative problems. First, give yourself a brief. Scan the entire puzzle, grid and clues, to determine the level of difficulty and the best way to start. Are there a lot of black squares, indicating shorter words and fewer crossings between across and down? Are the clues very short, giving less context and thus more possible answers at the beginning? Are there any clues that seem to share a similar structure or theme?

After the brief, make a plan to approach the solve. With an easier puzzle, it may make sense to simply start from the first clue and go in order. With a harder puzzle, focusing on shorter answers to build some context for the larger ones is a good way to begin.

During the process, take some steps back to evaluate. Take frequent breaks from the clues to look at the full grid, and notice if there are any squares you can fill in by looking at the words around it rather than getting the context only from the clue. And you can always ask a friend or look up an answer when you get stuck. You’ll probably learn something new!

Once you’ve completed a few grids, you’ll start to notice patterns in the way clues are worded, or answers that frequently occur, and these observations will make your future solving more efficient.

But Don’t Let Answer-Driven Thinking Take Over

Crossword solving has limitations for creative thinking, because crossword thinking is based on questions that have definite answers. The problems we face as creatives, though, don’t come with answers already determined. Unlike in a crossword puzzle, there are always multiple solutions to our problems, and all the pieces rarely lock into place perfectly. In other words, the answers don’t come easily — and they shouldn’t. Not before asking a lot of good questions. Creative questions require a more thoughtful response.

I’ve caught myself occasionally falling into the dangerous habit of applying crossword-based, answer-driven thinking to a problem. To break that habit, I’m examining the questions I ask in a project. Are my questions open-ended? Are they designed to further discussion? Are they short, giving less context and thus more possible answers? (I guess crossword thinking can apply sometimes!)

I’m grateful for the lessons a life of crossword solving has taught me. It’s helped me to think on my feet, make connections, and mentally relax. But when it comes to solving real problems, it’s best to leave the easy answers to trivial pursuits.