I’ll finish up this guide by talking about what actually happened to me between September of 2020, when I decided to come back and try to make master, and October of 2023, when I accomplished the goal.

When I sat down in 2020 and mapped out a plan to come back, I didn’t know if my goal would be easy or impossible, but I did know what I had to do. I had to build a usable opening repertoire and improve my understanding in slow positions and endgames. Now that I was living in Pennsylvania, about an hour north of Philadelphia, I decided to prepare to play in the 2021 World Open, played over the July 4th weekend. My strategy was to watch a lot of Gata Kamsky to try to learn endings and slow positions, and to use the Lichess opening explorer and Stockfish to build a decent opening repertoire.

I really worked at it. When I look back at it now, I shake my head at the things I was doing, but I hadn’t refined my techniques yet. I was just figuring things out. One thing that I did that never changed was to map out specific time to work on the project - at least 30 minutes each morning before work on weekdays, and between one and five hours each weekend.

Watching Gata Kamsky was indeed helpful, but only so much. Early on I decided I was not a fan of Kamsky’s openings, so while watching his endgame play was helpful and seeing how he made decisions was useful, many of the actual positions I was looking at on his channel were ones I never wanted to see in front of me personally.

My first attempt at the construction of an opening repertoire was also not ideal. I didn’t have a lot to start with, given that I felt that the openings I had been playing in 2004 were not great and too tactically-oriented for what I would be successful with as an older player. Not knowing much about what many openings were like, I picked a grab-bag of openings to prepare that seemed like they wouldn’t have too much theory but were sound. I put together lines that Stockfish liked and that had performed well in master games, and wrote rules for myself to learn the basic ideas. I collected model games from my openings played by strong players from the past that I wanted to emulate.

There was a ton to learn, but by the time the 2021 World Open rolled around I was feeling cautiously optimistic. It turned out to be a bracing jolt of reality. In round 1 I actually outplayed an FM from the black side of a Nimzo-Indian, but spent so much time doing so that I had about two minutes to make 15 moves before the first time control. In those 15 moves I turned my win into equality, then my equality into a loss, then I actually got checkmated. In my second game I got the better end of the white side of a Scotch against a strong master, got a modestly better exchange up ending, and completely misplayed it to lose. In my third game, I played a 2200 player, completely forgot the move order of my opening line in the black side of an O’Kelly Sicilian, and while I was able to confuse the issue for 60 moves I was unable to ever fully recover. So, an 0 and 3 start. My games improved from there, mostly because I kept getting the Scotch on the board and nobody really understands the Scotch, but it was clear that I was pretty rusty, my understanding of the positions I was reaching was haphazard at best, my memory for remembering my openings was not great, and my endgame play was still fairly poor. I finished the tournament five rating points poorer, but much more aware of the scope of the project I had set for myself.

I kept working through the second half of 2021, especially discovering the value of sparring endgames with Stockfish and playing both sides of a position over and over, but my repertoire preparation remained sub-optimal until I finally decided to try out Chessable in January of 2022. On the Chess Dojo Twitch channel I had seen Jesse Kraai drilling his own lines using Chessable, so I finally decided to try out the 2021 course of the year because it looked interesting - Keep it Simple for Black, by Christof Sielecki. It was a revelation. Many of the lines were really interesting, but the most important aspect was that he was using similar ideas and approaches across lines to keep it easy to remember. I started learning it to use as my complete black repertoire.

Also in early 2022, I decided that I wasn’t enjoying most of the positions I was reaching with white, and to finally make the jump to stop playing 1. e4. I had been a king-pawn player my whole life, but I wasn’t loving most of my options against 1…. e5, the Sicilian, or my personal bugaboo, the French. I decided to switch to 1. d4, building a repertoire around an opening I had always admired from afar - the Catalan. I’ve made a lot of questionable decisions in my opening prep choices, but I’ve never regretted learning the Catalan. It was a great choice for me.

I was getting a lot out of Keep it Simple for Black, but I was also realizing both the upside and downside of using somebody else’s opening course. Sielecki had done a great job of selecting interesting, sound, and easy to remember plans, but I didn’t always like his suggestions and above all I felt like the lines ended way too soon. It often happened that in an online game I would reach the end of one of his lines and not have a clear idea of what exactly to do a few moves later. I started building my own lines in a personal Chessable course like I’d seen Jesse Kraai do, based on my own experience with what I needed.

Using the ideas I’d gotten from Sielecki’s course - mapping out common, generally-applicable plans rather than trying to maximize the Stockfish eval or the winning percentage of a move in master play, I started to map out long lines and work on them. That’s when I really started to fall in love with this type of work. Stockfish is fantastic at finding surprising yet sound approaches to positions, and I loved playing through these fascinating lines it would find - just like I loved playing over Tal games when I was younger. I started focusing on the inspirational aspect of some of these longer lines I was creating, and really making them more like the model games I had first enjoyed as a young player - but ones where I had a lot more control than I did with model games played by real-life strong players. It really clicked for me, when I realized that it could be inspiring to do what was nominally opening work. Today, when I want to love chess I play through my lines - and I built my lines specifically to have that effect. Incidentally, when I want to hate chess, I play bullet.

In September of 2022 I once again felt ready to try to play over the board again. I decided to take a flyer and play in a local Saturday quad tournament. It turned out to be another turning point.