M2M Day 260: I think I’m finally wrapping my head around this

Max Deutsch
3 min readJul 19, 2017

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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.

Yesterday, I built the Letter Trainer, which is a computer program that theoretically helps me improve my mental representations of common crossword letter patterns.

I experimented with the Letter Trainer during my commute today. It seemed useful, but I still need a little bit more time before I can declare whether it’s effective or not.

Until then, I want to share a new framework that I’m using to better organize my thoughts around my training approach. The framework is broken down into three parts, based on the three stages of solving a crossword puzzle: 1. Beginning, 2. Middle, and 3. End.

1. Beginning

In the beginning of the puzzle, my main objective is to lay down as many high-probability answers as possible based solely on the clues (since the grid is empty, not offering any ‘helping letters’ for support). At this stage, it’s important that I’m familiar enough with the most common crossword clues and answers, so I can have an entry point into any given puzzle.

To train for this, I’ve been using my Crossword Trainer to memorize the 12,000 most common clue-answer pairs from past Saturday NYT puzzles.

My training approach for this “Beginning” stage is fairly solid.

2. Middle

Based on the initial answers I lay down in the “Beginning” stage, I should be able to build momentum and fill in a decent portion of the puzzle. At some point though, I seemingly won’t be able to make any further progress.

When I reach this point, I need to start relying less on the clues and more heavily on the patterns in letter frequency, adjacency, etc. to make forward progress. This is basis of the Expanding & Contracting approach that I explained a few days ago.

As I determined yesterday, I’m able to train for the “Middle” part of the puzzle using my Letter Trainer. I still need to determine the optimal way to structure my Letter Trainer practice sessions, but at least I have a directional plan.

3. End

Eventually, I need to fill in the last few squares, check to make sure that I haven’t made any typos, and complete the puzzle.

Interestingly, because I’ve only been practicing with previous Saturday puzzles (for the most part), which I can’t yet solve independently, I effectively have no practice finishing a crossword puzzle (that I didn’t cheat on in some capacity).

I don’t want to assume that finishing a puzzle is just doing the “Middle” part until the puzzle is done. So, I need to start exploring what this “End” part looks like, and then extrapolate whatever I learn into a plan for my Saturday puzzle execution.

To do this, I’ll need to start solving some easier puzzles. Perhaps, Wednesdays.

I’m glad I’ve organized my thoughts in this way. Without doing so, I may have overtrained for the “Beginning” part of the puzzle, and significantly undertrained (if at all) for the “Middle” part and especially the “End” part.

I now have a reasonably clear end-to-end picture of my training process, which will help me prioritize my next 13 days of training more effectively and holistically.

I’m finally starting to wrap my head around this…

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.

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