I work on mainframes and dislike Java. Conservatism is not a problem, my problem is I perceive lot of Java people being pretty smug, and they are just because Java is #1. (And I also worked in C#, so I know the difference. Java itself is not the thing that makes people smug about it, it's the position on the popularity ladder.)
I mean, if your approach is, we use this old and tested language, it has many warts, but works for us.. good.
If you go, well, we use this language, because it's #1, and therefore it's clearly the best in the world.. no, thanks. I know Forth and Lisp and Haskell, and I know the world out there, which you don't, so I know for a fact there are innovations that didn't make it to Java yet, or pretty badly.
To me, humility in programming is (partly) don't think your tool is the best just because it's the most popular one at the moment.
Finally, this perception of Java is changing (it is being slowly dethroned by Python and JS and other contenders), and with that will come more pragmatism (less of crazy OOP and patterns cargo cults), which will actually make it more likable in the future.