My grandfather was a long-suffering Cubs fan who never got to see a World Series victory, so his life begs for a baseball analogy. I'd say he hit a grand slam (to extend the metaphor, his three daughters would be the base runners). He started out with little -- he had to quit high school to work -- yet achieved everything he wanted in life (family, career, wealth, leisure, etc.). I don't think he had many regrets, if any.
What about my own at-bat in the ballgame of life? I hit a long fly to the right field corner that dropped just short of the fence. I got a double, but half the fans are disappointed because it wasn't a homer and the other half are disappointed because it could have been a triple if I had run faster. Such potential for greatness, and look where I ended up. I'm standing there on second base thinking, A double is pretty good, isn't it? But it's hard to feel good when the whole stadium is booing.