M2M Day 267: Originally, I came to the completely wrong conclusion

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.

In retrospect, the Crossword Trainer (the computer program I wrote to memorize the 6,000 most popular crossword clues and answers) was hugely important to my success this month.

However, I didn’t always think so.

On July 9th, I analyzed the Saturday July 8 NYT crossword, revealing that only four of the answers in the puzzle exactly matched clue-answer pairs in my training dataset. If I assumed that clues didn’t matter, then 45% of the grid would be filled with answers from my dataset, but this felt like a faulty assumption (and so, I determined that I couldn’t count these answers as automatic).

In other words, even if I spent 30+ hours memorizing the entire dataset, I would barely get any measurable help on actual puzzles.

Therefore, at this point, I mentally decided that the Crossword Trainer was a waste of time, and I stopped using it.

Yet, after a few days without the Crossword Trainer, my progress flatlined (or perhaps even regressed). So, I realized the there was something beneficial about the Crossword Trainer — I just didn’t know what.

Now, with two additional weeks of experience with the Crossword Trainer, I realize that I came to the wrong conclusion originally: It didn’t matter if I remembered the particular clue for a given answer. Instead, it was just important that I had exposure to the answers and exposure to the clues — but not necessarily as “pairs”.

I’ll explain this idea further tomorrow, but for now, I want to lay out the empirical evidence:

Here’s the Saturday puzzle that I successfully solved a few days ago…

Here’s the same puzzle, but I’ve highlighted all the words that I memorized as part of my training with the Crossword Trainer. I’ve also included “As Ever” and “In Toto” because these are answers I remember seeing from other crosswords (even though they weren’t in my dataset).

Two weeks ago, my original assumption was that most of these words wouldn’t be automatic (since I memorized most of these answers in the context of very different clues). In other words, it wouldn’t materially help me to memorize them.

However, if you watch the video of my solve, you’ll see that, with the exception of DESADE and AFI, all these other answers came to me almost instantly.

Empirically then, my original analysis seems wrong: By memorizing just these answers, I was able to mostly get these words for free, giving me enough momentum in each section of the grid to fully complete the puzzle.

Tomorrow, I’ll try to explain the theory and my explanation for this empirical observation.

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.