I have one character who is nearing retirement, as well as several others. As I contemplate this character's history, I realized that I only really remember the highlights - becoming a vampire, defeating Volsung, becoming leader of the thieves' guild, but forgetting a lot of the details or mixing them up with my other characters' accomplishments. So for my next character, I've decided to keep an adventure journal. So far I've logged that character's efforts at joining the Companions, and so far I'm really enjoying it. Has anyone else tried this? Do you find that it enhances gameplay? Did you eventually get tired of writing it all down?

I haven't tried this, but I imagine your characters story would be much better and more detailed.

I had a mod for Morrowind & Oblivion that did this..

you could write your characters Journal in-game, and the Oblivion version even allowed you to export it to a .txt document...

sadly, I have not found such a mod for Skyrim...