I think you may be forgetting the natuer of nuerons here. You can't just clone a memory into another body. You have to physically alter the noerons in the brain itself. As you do that, there is less and less of the person's personality, and everything else left. Once you start to restructure one opart of the brain, the other structures alter as well. Plus you have to factor in the fact that no-one has a brain wired the same as anyone else, meaning that the structurs of the brain are similar, of cousre, but the actual nueral composition is not. The old sci-fi question of "Do I see red the same way as you do?" comes into play here, Especially since the answer to that question is "no."
To even have a remote chance of this working, you would need a clone, like you've already said. But you would need a clone who is the same age as you. After all, 50 years of corporate experience means very little to a person who is going through puberty. All those hormones and the like would play all kinds of hell with those precious memories and personality traits. Everyone has the fantasy of going back in time and reliving a few select days of their lives knowing what they know now. Just think how that would change you. So your really wiz and obscenely espensive plan to copy yourself and live forever would amount to, very quickly, creating a "you" who may well not do ANYTHING the same as you ever did, and hate the idea of what happened.
Gabriel