That’s pretty weird and uncomfortable and I don’t know that I would want to work with someone like that in or out of office.
It's not a tech problem, it's a culture problem. Just because the infrastructure is old does not mean that it is bad. The main deciding factor is how well it is maintained. But that is to hard for many people. So much easier to say "It'S bAd bEcAuSe iT is oLd" and walk away.
It’s easy to complain about modern airlines (and I do), but it’s still true that’s never been cheaper to fly, and IT infrastructure is surely no small part of that.
Most of the reasons Java dropped out of popularity no longer apply, and at this point it is an incredibly stable and mature ecosystem.
I can come back to a Clojure program I wrote ten years ago and it runs great, meanwhile a TypeScript program I write 6 months ago requires a bunch of updating and cleanup.
It's an uphill battle, but it might just climb the hill because it's still such a behemoth.