This is a question I've thought about from time to time. As I get older (ancienter?) I often find myself remembering moments from as far back as my childhood when I've said or done things I'm not proud of. If I was to survive death and carry those thoughts into another life I wonder if they would consume my awareness, making mere existence a "hell"? (Mind you, there's nothing particularly heinous there, but some incidents were not very noble, either.)
It's only a exercise in "what-if" because I doubt if anybody has ever lived who could look back over their life and say, "Boy, I was great. The world was so lucky to have me."
Even Siddhartha Gautama may have found cause for regret as he sat contemplating his umbilicus.