Does being an empathetic person make life more painful?

Should children be taught bartering, as we assume that many will have a future where there are few traditional jobs available, but plenty of time to develop useful skills?
How do you deal with the emotions when watching your child participate in a public performance for the first time?
Why would a man who I barely talk to (got around on the grapevine) cry about sad news about me? He also avoided eye contact with me when we did interact years ago.