Chess and uncommitted obsession
7 min read

Chess and uncommitted obsession

Chess and uncommitted obsession

I have recently started to play chess again after a multiple year hiatus*. I have discovered that chess is very much not like riding a bike, and I have made (many!) repeated mistakes.

As my frustration increased, I began to suspect that the cause of these mistakes was not due to a lack of brainpower, or understanding of rules of the game, or because I am bad at pattern matching. I think that they mirror a few key types of blunder that I often make in my personal and professional life, as well as pointing towards a deeper underlying fact about myself.

This seemed like a good chance for self-reflection.


Despite the fact that the best chess is now played by computers, I still find something romantic about the game. While I'm playing, I go through intense swings of emotion: from the cold logic of the opening, probing the opponents defensive shape, to the giddy excitement of closing the net of a trap - to fear and then frustration as you realise that you were hunted rather than hunter.

I like that it is accessible to the layman, with (in my experience) a relatively consistent learning curve. As you play, you can feel yourself slowly getting better at understanding the rhythm of the game, spotting dangers earlier and mounting attacks with increasing sophistication.

However, there is one place in my game where I have seen far less improvement. I often focus hard on advancing my pieces on one part of the board, and totally miss the position that has opened at the other end. Often, I will find myself having played 5 or more moves in one corner while hunting their king, only to not see that I have opened myself up on the opposite side.

This inability to see the wood for the trees has in the past been reflected elsewhere in my personal and professional life. Sure, there are times when it is a useful attribute - being able to go deep into a subject, break it down and rebuild that understanding from the bottom up. But just like not seeing the danger on the other side of the board, this often leads to failing, or falling behind, in achieving the overall goal.

I often find myself not doing the thing I was supposed to do, because I was instead doing something simpler and/or more exciting (often deeper into the detail). On a few spare hours on a recent weekend, I was meant to be clearing out a cupboard in my flat, and ended up spending most of it cleaning up a scruffy pair of trainers.

That might not sound more interesting, but I have always enjoyed repetitive physical tasks with low decision-making load that have a visible outcome. I now have nice white shoes, but that cupboard is still full of old junk.

For a while at work, I have been trying to build a dashboard to display some key metrics about a project. When I started, I ended up finding something else out about a part of the calculation for some metric - and then spent four or so hours digging deep to see how that was being calculated, and writing up notes on how we might do it differently.

Was this entirely a waste of time? No, because I gained a far greater understanding of that underlying issue, and now have a roadmap to fixing it (or, as is probably more useful, passing on that information to someone else to fix). But I don't have a dashboard.

In chess or life, very rarely is it possible to achieve the biggest goals without strategic thinking about how to get to where you need to be, and consistent focus on that plan. I have to remind myself to at regular intervals take a step back, look at the bigger picture, and re-evaluate what's important.

Maybe then I'll stop losing so many damn games.

Doubling down

I recently listened to a podcast from Radio 4's More or Less series about detecting fraud in chess. It was interesting that it's pretty simple to detect the difference between players who are cheating and those who are not - the players who aren't have a plan.

Computers don't need a plan, because they re-assess the situation every move and aren't afraid to work their way out of a position if that's the best thing to do.

I find myself utterly unable to think like this. When I put into place a plan - perhaps a piece exchange that will lead to pinning a bishop - if the opposition behaves differently to how I expected I will try and find another way to make it work. I lose a lot of games chasing a plan that isn't available any more.

I enjoy walks with my partner where we don't follow a trail, and therefore are reliant on getting lost then un-lost later on. On a positive note, this often leads to discovering interesting things that aren't on the map. It also leads to walking for much longer than you intended to.

A few weeks ago we were lost, and I was following what I thought was the right trail to get us back to the car. It was not, which became evident as my GPS managed to catch up with where we were (far, far away from where I assumed).

Instead of doing the smart thing, which was to turn back and figure out where we lost the trail, I attempted several madcap schemes to take us down muddy, steep bike trails which were vaguely in the right direction. We eventually turned around, much grumpier than we started (at me, in my partner's case).

When I run experiments in my job that I have a too-strongly-held hypothesis will work, the problems begin when they don't. My first reaction is to question the data, ending up with rewriting well-tested code, which is not a good use of time. My second is to wonder whether a slightly different application of the same idea would have worked better. This is a very easy trap to fall into, but where you have limited time and resources it's rarely worthwhile to tweak after a failed test (as opposed to testing something different).

When two reasonably powerful computers play checkers, which I understand to be a weakly solved game†, it always results in a draw. Which is to say - there is no such thing as an interesting game where mistakes are impossible. The important thing is to know when to reverse course once you've made one.

Uncommitted obsession

I'm not entirely sure whether this is a unique type of mistake, a superset of the other two, or something entirely different.

Here's a relevant example; over the past few weeks, I have played over 250 games of chess on my phone or laptop. These games are of the type where you have a 20 minute time limit between you, and I would estimate they take on average 5-8 minutes per game.

That's more than an entire day of online chess, up from 0 minutes in the last 10 years. I've just played far too much chess lately.

Being an obsessive comes with positive and negative traits, but I think there is a real difference between committed and uncommitted obsession. The former leads both to great works and occasionally madness, while the latter leads to journeyman status in a lot of subject areas. I fall very neatly into the latter category.

Being an uncommitted obsessive means diving into a subject in a way that is deep but not broad, and then never returning to it. It means, as previously mentioned, if I can't find an answer quickly I will waste an evening but then move on before I have true understanding of the subject area. On my laptop I have quite literally hundreds of started but unfinished novels, ideas for art, business ideas, podcasts (and much more).

At work, I have sampled everything in the growth/product/marketing cabinet, from sending physical mailers, to using MTurk to scrape targeting data, to building peer-to-peer referral schemes and creating APIs for partners. I am no expert in any of these things, but I have seen enough to know a little about each.

I have to face it now; I will never be very good at chess, because it's not in my nature to master anything - I am great at getting passably good at a lot of things.

If you're an uncommitted obsessive, I think the key thing is to set yourself an intention when you get into something new. Asking myself where a good stopping point might be - and then re-assessing once I am there - helps to reduce the number of things that feel incomplete. Perhaps I should set myself a specific ELO score to hit on, then once I'm there I can quit for good (or not!)

Understanding mistakes and where they come from allows you to lean in to where your strengths are rather than fighting against them. I am a journeyman that loves to dive deep but not broad into stuff, and I don't think I should change that. That doesn't mean accepting the negatives - I think it means giving yourself checks and balances against them so that they don't weigh you down.

Now if I could just stop playing chess for a few minutes, I might finish a second post.

* Although I was not directly inspired by Netflix's The Queens Gambit, I think some friends mentioning they were trying chess after watching may have seeded the idea in my brain. I have since watched it and enjoyed it, though it's not really about the chess (and for good reason).

I find the subject of whether chess can be solved quite interesting. This is an article from 2007 on how checkers was solved, with some discussion on why chess is much harder and may require quantum computing.