Just had to interject another point:
Jesus said, "Surely I tell you TODAY you will be with me in paradise... Jesus used the phrase, "I tell you the truth" 73 times in scripture without ever adding an extra word like "today" to the end of it, so what would have been the point of him switching to a new phrase, "I tell you the truth today", aside from just confusing the meaning of what he was saying? The logical rendering of this verse plainly states that the theif would be with Jesus in the same place called "paradise" on that very day...
But anyway, I think JWs are trained to not "think outside the box". Everything about JW teaching is based on the assumptions that they already get the main jist of what God and life beyond this one is all about. Even going to the point of conjecturing all sorts of assertions of what He can and cannot do, that He's not omniscient, not omnipotent, not omnipresent, does not see the whole picture of what the future holds, Heaven is not an interesting place for most, etc. (even teaching as absolute truth at one point that he lives in the constellation Pleades, blah blah blah.). So everyone as a JW naturally thinks of the next life in terms of what they can understand about the present life, except that it's a "new and improved" version.
But if you step back and think about it, if you hold the assumption that the infinite creator of the universe has a plan for us after this life, and the very nature of the universe itself is way beyond our comprehension, then how much can we honestly expect to comprehend at this point about the very nature and possibilities of our future existance? I mean if someone lived in a cave their whole life and knew nothing about what the outside was really like, they may be pretty content about that cave and even look forward to living forever in that cave.
1 Cor 13:11-12 says, 11 When I was a child, I talked like a child, I thought like a child, I reasoned like a child. When I became a man, I put childish ways behind me. 12 Now we see but a poor reflection as in a mirror; then we shall see face to face. Now I know in part; then I shall know fully, even as I am fully known."
I guess what I mean to say is that we can accept that we don't have to quite understand all that is in store for us, but it could be better than any of us ever imagined. In any case we can choose to leave it in the hands of our creator and not let it consume us.