500 Days of Chess: A Retrospective
Two years after a booth at Holiday at the Park sent me home with a $40 chess game for my daughter, I hit a 500-day Duolingo streak. Here's what chess taught me along the way.
I started playing chess almost two years ago, shortly after teaching Zoey how to play using Story Time Chess. I recently hit 500 straight days of chess on Duolingo, which feels like a good moment to look back. I want to talk about what that was like, what I’ve learned, and what the future might bring.
My chess story started at Burbank Holiday at the Park. We take the kids every year to see the sights, and that year was no different, except that we came across a booth for a kids’ chess program that claimed to have a method for teaching children the game. I was mildly aghast at the $300/month price tag (and mildly impressed by the Hugh Jackman endorsement), but I noticed their classes were built around a game called Story Time Chess. A quick Google search showed I could teach my own daughters with it for the low, low price of about $40, and I bought it right away.
It works. I spent a good amount of time patiently teaching the rules to Zoey, who was just 5 years old then. We got through the rules and played a few games together, and she even beat me once. I didn’t realize until later that it wasn’t actually a real win, and I still don’t have the heart to tell her. She stayed interested long enough for us to reach the second book, but she gradually hit a wall and it stopped being fun for her. I was a little disappointed, but I let it go.
I think I was so keen on teaching her because I never got the chance to learn when I was young, and I wanted my kids to be exposed to it. I still remember stumbling through a chess game as a kid with a girl I had a crush on, and the humiliation I felt when it became obvious I had no idea what I was doing. We eventually drifted apart and lost touch, but that feeling stayed with me. Ever since, chess had been a hole in my life, like a missing puzzle piece.
Around the same time, Michelle got into it too, and we started playing each other. We were at about the same level, so it was a fantastic way to spend time together, and we’d often play three or four games a night after the kids went to bed.
Early on, we both blundered pieces constantly. Looking back, those games must have been hysterical. We would laugh it off and move on. Sometimes one of us would go on a winning streak, and the other would groan that there was no way to catch up. It never lasted more than a week or two before the tables turned.
It got serious enough that we bought a physical chess set, a $40 “luxe” set from Target. It just wasn’t the quality I wanted, so I spent days poring over the options before settling on a premium Staunton set. It was expensive, but not out of reach. Staunton is the classic design for a reason. The pieces are weighted, and that heft gives every game a sort of seriousness. The set also brought a particular kind of joy into our lives, since we rarely splurge on something that, in truth, we could play just as well for free.
A few months later, Duolingo launched chess lessons. I took to them quickly; working through them felt like doing a chess puzzle book. I finished every chess lesson Duolingo had to offer and simply kept going, playing games against Oscar, the app’s computer opponent, and against other players. Lately I’ve been doing puzzles, both in the app and at the board from a puzzle book. The streak recently passed 500 days, and honestly, I never had to fight to keep it alive. Playing chess every day stopped being a goal and became a habit.
Slowly we got better, and our matches got far more satisfying. It became normal for us to spend two or three hours a day playing chess, between the app and the board. That’s when I really started digging into chess itself: the strategy, and the culture around it. Michelle took a different path. As far as I know, she has never studied any theory. She just thinks deeply, in a way that looks effortless. These days I’m a little ahead, but it depends on the day, and there have been so many great games that I couldn’t pick a favorite.
Seeing the world through the lens of chess has taught me a few things. For example, in chess it’s often better to counterattack than to defend. I learned that one the hard way recently, when several people left my team at work. I had a really hard time dealing with it until I stopped defending and counterattacked, going after the problem head on. The idea of tempo is useful too. It reminds me that the best actions serve more than one goal. Carrying these lessons beyond the chessboard and into life has been one of the most valuable parts of this journey.
I’ve learned a lot in these two years. I rarely blunder now, though I still do it often enough that Michelle can count on me playing well early, then making some catastrophic mid-game error that hands her the win. More than any result, though, I proved to myself that I’m capable of climbing this mountain. The missing puzzle piece is in place.
As for what’s next, I want to teach Alyssa. She’s starting to get interested and she wants to learn, and I’m looking forward to giving her the same opportunity her sister got. I’m curious what lessons we’ll both have learned by the time my streak hits 1,000 days.