We have a super-robust set of tools for this for fiction; I'm still chewing through the list generated by 'all Pulitzer prizes for fiction written during my lifetime' - and all of them have been quite good. ('the Orphan Master's Son' so far has been my least favorite, though it was still really quite good. And because these were chosen /at the time/ you get a glimpse into what people were thinking at the time. Mailer's "The Executioner's Song" was a wonderful book in it's own right, but I think was also a historical slice of 'the discourse' at the time.)

For Movies, I find that Ebert aligns a lot with my taste. If he says it's good, it's really good. I mean, that doesn't help with recent movies, but there's more than enough of the old good stuff. (There's a lot to be said for consuming old media; it gives it time for critical opinion to stabilize. )

I mean, of course, all of these methods will leave out a lot of really good stuff. But... that's kind of the point; there's way more media than I can consume. There are professional reviewers that can give you more really good media than you could consume in a reasonable lifetime. I'm not quite halfway through the 'Pulitzer prizes awarded in my lifetime' list, and I've started a few years back. (I mean, I was 40 or so by the time I started, and so I had read a few of the books just 'cause they were popular books that people recommend. McCarthy's "The Road" is exactly the sort of thing I like, so I read it before on another person's recommendation. But still, like, you see some really great work outside your genre; I'm not normally a romance novel kinda guy, but Lurie's "Foreign Affairs" was absolutely beautiful, and absolutely not a thing I would have read without this project.)

I haven't completely solved the problem for technical books, just 'cause people who have good up to date knowledge of an area have often built up that knowledge over time. they read some books but those books are long out of date, they've brought their skills up to date with mailing lists, which they then vet based on their knowledge of the reputation of the person posting.

I mean, I think it's pretty easy for the non-perishables, "The C Programming Language" is a thing you should read if you work with computers. But which tomb on docker is up to date enough and pretty good? that can be a difficult question to answer, and is often answered based on the author's reputation for other technical work they do, which usually tells me something about the accuracy of the book, but doesn't tell me if it's well written or if it's up to date enough. (On the other hand, if you are well known for writing a big part of the subsystem I wanna learn, eh, I don't feel too bad about giving you money for a book even if I later decide that the book is not written in a way I find engaging, like, you earned it and I'll buy another book.) And... I dunno. often you can get sample chapters, and that gets you a pretty good idea of how engaging the writing is.

I mean, one way to address it is to start at the base... "go read the gang of four design patterns books, and then use your knowledge of object orientedness to make sense of modern object-oriented configuration management systems" - which does make some sense. But still, I should spend the time to find the tech book awards that match up with my taste.