It does seem that many people take it to be a given that if it’s common to feel intensely sad (or happy) in some kind of situation, then that emotional response is the most appropriate. I take what you’ve written here to give us reason to think otherwise.

I’m reminded of a book called The Choices We Made: Twenty-Five Women and Men Speak Out About Abortion, which details the responses, from extreme and lifelong guilt to relative harmony, faced by those who had abortions. It seems pleasantly honest in comparison to much of the rhetoric surrounding the issue.

On a more abstract level, the question is about what psychologists call “resilience,” and the New York Times wrote about the phenomenon in A Question of Resilience, which discusses why some people, like Lessig, move with what appears to be ease past difficult events, while others do not. It focuses on a genetic variation, implying perhaps undue power, but it’s nonetheless an interesting discussion of the people who often get left out of the debate: the “person A [who] shrugged off the same experience that traumatized person B.” To deal with one of your other examples, the blog Confessions of a College Call Girl has some posts dealing with past problems that the writer haven’t apparently hindered the writer in her career.