If picking as a starting poker position, I'd definitely want to be the 25 year old with a thousand because you'll be able to play more hands and have more experiences and hopefully have more fun even if you'll most likely end up very average or lose your entire chip-stack. I guess what I'm saying is there's no virtue in poverty and no guarantee wealth will bring you ultimate satisfaction either. Your choice is a false mutual exclusivity imho (in that everyone is 25 AND 95 [assuming that that they in everyone lives to 95], someone wanting to be 25 again doesn't imply that their previous journey to 95 is somehow intrinsically worth less - like an adrenaline junkie wanting to ride again the rollercoaster he just got off from).