M2M Day 244: I wish I had a better plan

Max Deutsch
3 min readJul 3, 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 started a new challenge: I’m attempting to solve a Saturday New York Times crossword puzzle in one sitting without any aid.

However, there’s an additional wrinkle to this month’s pursuit…

As I explained yesterday, there is no known systematic method to becoming a predictably better crossword solver. Thus, my secondary challenge this month is to uncover a predictable and accelerated training method that I can actually use.

This may be particularly difficult, since it’s likely that no such training method exists (as I discussed yesterday). If this is the case, I’ll need to resort to a purely brute force method, which is less than ideal.

It will definitely be interesting to see how this story develops throughout the rest of the month.

In the meantime, here are a few ideas that will help me get going:

1. Start by solving a lot of puzzles

My initial plan is to start off by solving (or attempting to solve) a dozen or so Saturday NYT puzzles. In doing so, I will hopefully identify my main inefficiencies, bottlenecks while solving, etc., which I can then remedy through more intelligent, targeted training.

In other words, I’m going to start off with a lightly more mindful version of the brute force method.

2. Study solved puzzles

Given that crossword puzzles can theoretically contain clues and answers from an infinite knowledge base, there’s a lot of obscure information that I’ll need to learn this month.

From past experiences solving (mostly Monday puzzles), I’ve noticed that I slowly absorb crossword knowledge over time, as patterns start to emerge. However, to acquire this knowledge at the appropriate pace, I don’t think I can rely solely on the passive, brute force method. The math just doesn’t work out:

The average Saturday puzzle takes me between 20–30 minutes to “complete”, which means I’ll only be able to work through ~60 puzzles during the entire month.

There’s no way that I’ll get exposure to the majority of the crossword lexicon solving only 60 random puzzles, so I’ll need to accelerate this process somehow.

One idea is to simply read through already solved puzzles, identify patterns (i.e. clues/answers that occur more frequently), and then memorize/internalize accordingly.

I can likely read through 10 puzzles per hour, which means I can work through 60 puzzles in less than a week, instead of a month.

This honestly still seems like fairly low volume, but it’s a step in the right direction, assuming this method is engaging enough (which I’m not so sure it is).

3. Memorize the most frequently used clues and answers

If reading through solved puzzles still doesn’t give me exposure to a large enough dataset, I’ll need to take an even more extreme approach, where I aggregate all crossword clues and answer from every puzzle ever, sort them by frequency, and then memorize the most popular answers up until some threshold point — completing removing the context of the puzzles.

I’m not too thrilled about this method either, but it’s an idea.

Clearly, I don’t have much of a plan yet. All three of my ideas are some flavor of the brute force method, which certainly can’t be classified as “predictable” or “repeatable”.

Hopefully, once I start solving more puzzles, I’ll find some magical insight that will change everything. But, I’m not holding my breath…

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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