I wouldn’t put “chess” onto my resume unless I was at least titled. Otherwise, what is a signal that it sends to the hedge fund crowd of overachievers? That you have a hobby that you managed to not get good at?
If someone lists ‘skiing’ as a hobby I’m not expecting them to have Olympic medals to back that up. ‘It says here on your resume that you play guitar. Well, let’s see how you fair in a guitar battle with Slash from accounting’
This is just more of that hyper competitive ‘well rounded college applicant’ performative high school stuff, isn’t it? It’s not enough to just have an interest - you need evidence of performing at a competitive level.
Likewise I wouldn't list chess unless I was good enough to at least entertain a grand master for a few minutes.
Guitar is a performance art. Mediocre people are entertaining. Chess (and skiing) mostly isn't.
I wouldn’t put down ‘travel’ as a hobby if I weren’t prepared to take the interviewer on a quick day trip to Paris.
I wouldn’t list ‘reading’ as a hobby unless I could do a professional audiobook-level reading of a book for the interviewer, including doing all the voices.
I think if you put a hobby on a resume for the purpose of signaling some kind of orthogonal skillset ostensibly related to the job (like in this example, "strategy"), it stops being just about your personality and becomes explicitly performance-oriented. And I would even argue your resume is not the play to round out your personality, because it's such an overly subjective and bias-inducing thing.
It's dumb to lie and say you enjoy chess when you don't, just like it's dumb to put any other lie on a resume, but if you do enjoy it then there's nothing wrong with communicating that you're the type of person who enjoys chess, which means you are probably a person who enjoys somewhat adversarial situations where you need to win with your logic and you are comfortable with taking short term losses for long term gains, a personality which would likely be both comfortable and familiar in a hedge fund environment.
Sure - to which my next question becomes, are you actually good at it? If you're not, I don't professionally care if you personally enjoy it.
Let's say you're hiring people to work a fish market. One candidate loves going out on the boat and fishing in their spare time, the other hates the smell of fish. Both are fully capable of doing the job, which doesn't involve catching fish or being on a boat, but which does involve spending a lot of time with dead fish. Who do you think is more likely to stick with the job for an extended period of time and be pleasant to work alongside?