M2M Day 253: A nice counterintuitive trick

This post is part of Month to Master, a 12-month accelerated learning project. For July, my goal is to solve a Saturday New York Times crossword puzzle in one sitting without any aid.

So far this month, my training has been almost exclusively focused on two things: 1. Memorizing the most popular crossword answers and 2. Learning how to identify and interpret the main types of cluing misdirection.

One thing I haven’t put too much time into is solving technique.

In other words, what’s the best way to actually approach a NYT crossword puzzle? Or, more specifically, based on my current knowledge of clues and answers, can I improve my puzzle-solving abilities through some sort of solving-focused optimization?

In reviewing my practice logs (and some screencasts of my solves), I noticed an interesting pattern in my approach to the puzzles:

  1. First, I usually work through all the Across clues and all the Down clues, in order, filling in all the words that I know right away.
  2. I then find the most densely filled-in part of the grid, and work my way through that area until I get stuck.
  3. I proceed to move around the rest of the puzzle in this way until I can’t solve anything more.
  4. Then, I use the “Check” option to reveal how much of the puzzle so far is correctly filled-in. Typically, I’ve made a few mistakes, and I erase those.
  5. Somehow, after erasing the incorrect letters, I’m able to make more significant progress, using the newly-created empty space as cues to reassess the corresponding clues and assumptions that I made.
  6. Eventually, I can’t solve any more of the puzzle and will “Check” again, erasing everything that I’ve gotten wrong. And so on.

In my mind, before going through this exercise, I imagined that I was mostly using the “Check” functionality as a way to validate my not-so-confident guesses. But, in reality, I’m using the functionality as a way to invalidate my guesses.

This might seem like the same thing, but the distinction is important: My ability to move forward is often more predicated on knowing when something is not the right answer.

So, here’s my idea: When I get to the point in a puzzle where I’m completely stuck, I should just assume that I’ve made some mistake somewhere. Then, I should search through the puzzle, find the answer I’m least confident about, assume that it’s completely wrong, and erase it. Then, hopefully, this manufactured anti-knowledge helps me make forward progress. If not, I should then remove the next least confident answer, and so on, until I start building forward momentum again.

This might sound like a horrible idea, where I end up erasing the entire puzzle, but, despite it’s counterintuitive nature, it seems to be working.

Today, I put this idea into practice, while solving a Friday puzzle from 2017. Fridays are almost as challenging as Saturdays, and since the puzzle is from 2017, none of the clues and answers are in my training set — so, this is a genuine solve. (I’m saving the 2017 Saturdays for later in the month).

In 20 minutes, I was able to almost completely finish the puzzle, with only a few blemishes in the northwest corner.

I wasn’t sure if this was just an extra easy puzzle, so I headed over to Rex Parker’s crossword blog to see his opinion. He thought this was a “Medium-Challenging” Friday puzzle (which likely equates to an “Easy-Medium” Saturday puzzle), so I was pretty happy about that.

Still, it will be interesting to see if this was just a fluke, or somehow this delete everything until I can make forward progress approach is actually an effective method.

Despite it working, it still feels like a bad idea.

I’ll try it again tomorrow and find out.

Read the next post. Read the previous post.

Max Deutsch is an obsessive learner, product builder, guinea pig for Month to Master, and founder at Openmind.

If you want to follow along with Max’s year-long accelerated learning project, make sure to follow this Medium account.