Hi,
As a dev, then software architect/devops guy, then CTO of my own startup, I've always relied on the following tools:
* Java (as my "base" skillset, but somewhat rusty after a bit more than two years not actively coding)
* Python, either for scraping, admin or math related stuff
I don't have much experience in front end development, although I understand it and can manage a team doing it.
I have friends that swear by nodeJS, I've looked into it but my "dislike" for JS (and all things front related really) make me fear I won't be good at it.
So what would my fellow HN users recommend as a new skillset to acquire, mainly to keep on top of new things and breathing a bit of fresh air outside of my day-to-day tasks?
Since you seem to be rooted in the web/OO world, taking a free Haskell course might be pretty interesting and mind-expanding for you. It'd also help you become a better web/OO developer.
Take a look at Elixir, Rust, Go, and Scala, and see if any of those pique your interest. If it's just for fun, it doesn't matter what you choose.
(IMHO Node sucks. JavaScript is widely known and popular because browsers don't support anything else. Unfortunately, it's an absolute mess, and the Node ecosystem is incredibly confusing and crowded. Things like Typescript are improving JS a bit, but it's far from the "best" language for something large. It's still good for prototyping, though.)