One of my dear friends recently posted a blog entry about an article about celebrities writing letters to their younger selves - cleverly titled Dear Me. Our diversity groups at work have had similar exercises, the results of which people within the group have shared.
I've done this exercise in my head many times. Maybe I have watched and read too much sci-fi and have "seen" the bad things that can happen because of messing with the timeline, but I always end up on the skeptical side of making changes. ("Back to the Future" is probably the most widely known example. If you're more geeky, Star Trek: The Next Generation had an episode called "Parallels" which discussed alternate realities. Star Trek: Voyager had several episodes dealing with time travel and the "temporal prime directive" and how bad things can get when you mess with time).
In any case, it's always been very hard for me to come up with things I would actually tell my younger self, for fear that I would actually make things turn out worse somehow. Maybe that is a testament to how well I think my life has turned out (?), maybe I haven't made too many major mistakes (?). I always come up with about 2 or 3 very specific things I'd probably like to undo (I won't share these :) But I also think I might encourage my younger self to not be so afraid to do things - almost every regret I come up with is usually something I DIDN'T do.
My friend and I also agreed that maybe the point of the exercise is to make sure you learn from your mistakes (since you can't actually go tell your younger self stuff).
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