Jeremy Felt

A year of crosswords

I think it was right before the flight from Seattle to St. Louis took off last year when I decided I would like to try regularly doing the NY Times crossword puzzle. I opened the app on my phone, downloaded a few puzzles before we took off, and didn’t know what I was getting myself into. I completed a ton of minis first, because they’re quick and generally simple. They also come with a leaderboard, which provides for competition, which provides for more fun.

Over the next month or so I poked around a bit and tried to figure my way around. I had a chat with Boone around that time and he gave me some great advice along the lines of “being good at crosswords doesn’t mean you’re smart, it just means you’re good at doing crosswords.” This helped frame things for me in a way that made me just start doing crosswords. Over December and some of January I went back and did every Monday puzzle from 2019 as practice, while also attempting many of the daily puzzles.

The NY Times crossword app provides a fun archive view that shows which puzzles you didn’t start, which you did, which puzzles you finished, and which you finished on the day they were published. The general target, if you’re slightly obsessed, is to maintain a streak of puzzles that you finish on the day they were published.

Here’s what December of 2019 looked like:

A screenshot showing the status of various crosswords published in December 2019.

I was doing pretty good on Mondays and Tuesdays. Wednesdays were still difficult. The rest of the week was still terrifying. I don’t know why I didn’t even start a Thursday. Of course now I don’t know why I do.

Things continued to get better. By March I was attempting most puzzles. I completed my first Thursday, Friday, and Saturday puzzles—some of them even on the same day. And look at that nice 4 day streak to close the month!

Doing the crossword every day became a nice break from the pandemic and a way to zone out with words for a small chunk of time. It was around March and April where it probably became somewhat of an addiction.

April, May, and June were each progressively better, but I’ll skip ahead to July, where things really clicked.

A screenshot of my crossword progress from July 2020.

For the first time, I finished every puzzle of the month on the day it was published! This was part of a 53 day streak and I was starting to feel like I had made it. If I could do the puzzle 53 days in a row, I could do it for thousands!

But at the same time, I was kind of stalling out. I could complete Monday and Tuesday just fine, but would look up a few things on Wednesdays and then lean on Google, Wikipedia, and the NYT Wordplay blog to fill in several leftover blanks on Thursday through Sunday. In general, I would get tired of doing the puzzle if it started reaching that 45 minute mark, but also didn’t want to end any streak I had going.

I had two incompletes in August, one in September, and finished with a perfect October. Then everything fell apart.

A screenshot of my crossword progress in November 2020.

Things got really busy in November. At the same time there was a Wednesday puzzle (I don’t remember which) that kicked my ass in a way that made doing puzzles not fun all of a sudden. I kind of gave up on the harder puzzles for a few weeks and focused on the more relaxing Monday through Wednesdays.

I also decided that if I wanted to pass this plateau, I needed to stop looking things up as often. So I ditched the streaks and got bad at puzzles again.

A screenshot of my crossword progress from December 2020.

This turned out to be a liberating process! I was no longer stressed about finishing a puzzle by the end of the day and no longer stressed about whether they were complete. For a bit of November and for all of December, I started treating each puzzle as ongoing. I’ve gone back to each unfinished puzzle in December several times now, trying to work out those annoying little sections as if they were part of a puzzle rather than an answer to lookup.

The progress has come fairly quickly. Each completed puzzle in December was done without lookups during the initial fill. My general rule has become: fill the entire puzzle and only then try to complete it with a glance at the Wordplay blog and comments.

My favorite take away from the last couple months has been finally being able to treat the puzzle as designed—a puzzle—rather than a series of words I need to memorize. The memorization and repetition helps, which is why doing all the Mondays from 2019 was a good idea and completing all of those Tuesdays and Wednesdays will be good practice next. But now that my brain has entered puzzle mode when approaching a crossword, I’m looking forward to the progress I’ll see next year.

Some stats that I may care to compare at the end of 2021:

  • Total puzzles solved: 426
  • Total puzzles started: 504
  • Solve rate: 84.5%
  • Longest streak: 53

And the current best times/average times by day:

  • Monday: 5:50/12:54
  • Tuesday: 9:24/19:16
  • Wednesday: 11:59/25:31
  • Thursday: 10:35/33:53
  • Friday: 19:30/32:50
  • Saturday: 21:26/37:02
  • Sunday: 40:49/59:08

I’m hoping that by the end of next year my current best times will have become my regular times for those days. Puzzles are fun, but spending less than 20 minutes on them is much more fun than 45.

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