I got a lot better at empathy from actively trying to understand people in contexts that 1) I wasn't emotionally tied up in, 2) were challenging, and 3) had concrete success/failure criteria. It is a fun game for me.

The way I did this was to gather up a group of online contacts and when they'd have issues like "I want to be more confident with women" or "I want to not be afraid of speaking in class" I'd try to understand it well enough that I could say things that would dissolve the problem. If the problem went away I won. If it didn't then I failed. No excuses.

I've gotten a lot better and it has been a pretty perspective changing thing. I'm quite glad I did it.