Imagine that you have some character trait that you feel you would be better off without. Imagine also, that you lack some trait you would be happy to have. If you now make certain decisions and commit yourself to them in due time you can, with good chance, achieve to become the sort of person you want to be.
But what if the person you become does not enjoy being the way she is? What if she finds some of her traits bothersome? Of she thinks others find it irritating that she is the way she is and maybe that's why she feels lonely. Maybe she should change...
The problem emerging from this scenario is the following one: if you value certain character traits now and manage to become the sort of person who has them, your scale of values and their ranking might change enough to make some of the values you have at this point seem worthless in your eyes. That is, there does not seem to be any chance to make yourself still feel attracted to the vision about what sort of person it would be nice to be, that you had earlier.
Is this the same type of problem that Jon Elster discusses, for example in his Ulysses Unbound? Not exactly. There, Elster is primarily focusing on how you can stay committed to a goal, when you know all along that the goal is good. For example, how an alcoholic can stick to his resolution not to drink, although he knows he will want a drink very badly when he gets home after work. The difference between this case and the case I mentioned above is, that the scenarios Elster discusses take it for granted that you know what the right is. You just need to stick to it somehow - you need to avoid temptation, temporal effects of scaling, etc. But you do not face an entirely new set of values. You just get into a situation where you temporarily value the bad thing. The changing-personality scenario is different. It portrays the possibility of a good change which you find meaningless once achieved. This type of problem has a pair in the field of decision making general (not constrained to altering your own personality).
There is an argument, made by L. A. Paul, in an article in preparation, in connection with having children, according to which no matter what you think now about having kids, that does not really matter. Actually having them is such a life changing experience, that you cannot now put yourself into the place of the person you will be after you already have kids. So, those problems that you might see with having kids are not sure to still be there once you have them. (Of course no one is saying that they might not, or that they disappear without a trace. But your priorities change.) Also, the good parts of having kids might be entirely different than what you expect. And this is just partly an issue of access to information about what it means to have a kid: you can get to know a lot by talking with your parents, relatives and friends, by working with kids, by reading about them, and so on. The information you do not have access to is this: what sort of person you will become. You might be surprised by finding joy in some things you would never have expected. Also, since what we care for influences the way we focus our attention and what we spend time on, you might find that you notice things about kids which you would never have done if you would have stayed your earlier self.
So, why is all this a problem? As Paul suggests, sometimes we need to be a bit crazy and make these decisions. One cannot find out sooner. Well, this might be true of having kids. But what about cases when for example teenagers are supposed to make choices about the job they choose? Or when it is left to politicians to decide about education? Or when one follows some self-help book for successful managers, and accepts its values and sets out to become like suggested? What do we base these decisions on?
There are two risks of making bad decisions in such situations: one is when we get to the point that we have changed, but we become a sort of person who does not care about being like that anymore. The other is that we misjudge what being that sort of person will be like: we thought we would be better, kinder, more courageous and just. But in fact we turn out worse and we don't even mind it anymore. We enjoy ourselves and the measure of what's a good life and a good person is gone.
It seems that in all these situations we cannot rely on anything else than on the experience and advice of those who have gone through changes we are thinking about undergoing. But we have to take into account that they are quite probably not able to occupy once more their perspective from before the change. Another thing that might be helpful is to have an objective value scale, which is sufficiently independent of our character to hold in place, no matter how our changes turn out to be. Having such a scale of values can help us orient ourselves even if the metamorphosis is a bad one. (Poor Kafka, he saw how many of his contemporaries by becoming 'bugs' adopt to their sad and constrained jobs which do not provide them with any sort of feeling of usefulness and pride in their work.)
I cannot end this post with any more particular suggestions. But I'm more than curious to read what you think, what you recommend me to read and how you handle such problems.
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