Optimistic?? I think the mind likes these extreme labels, but functionally they are false.
Further, I think an emphasis on optimism actually causes pessimism because it isn't true... when you go on hoping and hoping for the best and it never comes your mind eventually clicks into the opposite and expects the worst.
For me, in regards to any afterlife, I think that if you can cause happiness independent of situation during life the same will be true if there is anything after death. Even if you end up in hell, eventually it'll just be how things are so at least after any initial shock you will be able to be happy. Conversely, in any heaven, if you have the propensity to be miserable it will be no different there once the experience becomes monotonous.
I think a more subtle issue with your question, though, is in its orientation towards future success... even in the afterlife you want to continue striving towards some perfect situation. This means that the current situation cannot ever be enough for you, you always want more. This is actually the basis for all misery, and of course the definition of happiness is being content.
I think this is the only real choice we actually have, whether to be content or miserable with what is so... so I do not envy your current psyche at all because it basically can't be happy as it presently functions.