I think it's really incredibly challenging when you have an ability no one shows you how to manage. If you can imagine being raised by someone who's an experienced feeler of other people's emotions and that person, your mum or dad, says to you 'I know exactly what your problem is and I'll show you how to manage it beautifully, master it', that would be great. You could have your own in house teacher or instructor when it comes to how to feel and when not to feel so much. A lot of the time, it doesn't work that way unfortunately. If anything, we can be surrounded by people who more so say stuff like 'You're way too sensitive'. It's a 'What's wrong with you? Let's shut this fault of yours down' kind of statement.
May sound a bit strange but I've found one of the many challenges when it comes to feeling for others involves imagination. Distressing imagery can be a serious trigger for someone who feels so much, largely because you can feel what you can imagine, clearly see in your mind. If you can clearly imagine and therefor feel someone's intense sufferance, it's highly triggering. What you imagine becomes physical/emotional. Knowing when to shut your imagination down, in favour of pure logic or analytics or when to balance yourself somewhere in between the 2 can be a challenge. I suppose it depends on the situation, what you need to gain from it. Imagination, that which receives and generates imagery, is an incredibly powerful and sometimes overwhelming thing. It's a tool that can feel like a curse at times.
It's interesting, the ability to feel what others feel. I know of a woman who takes this to a whole other level. While initially fearing she was becoming a hypochondriac, she found herself going off to see the doctor on a fairly regular basis. Chest pain, back pain, headaches, you name it, she had it. While the doctor could never find anything wrong with her, someone close to her led her to wonder whether she was feeling what others were feeling. So, she began to ask. If she felt chest pain, she'd ask the person she was with whether they had any pain in the chest. Shocked, they'd reply 'Yes'. Back pain? 'Yes' etc. She began to advise people to seek medical or emotional help, in a variety of ways, which made an enormous difference to them. The challenge came down to fine tuning this ability, in relation to whether she felt them experiencing heartbreak or serious heart issues. As I say, this takes feeling for others to a whole new level :)