The Seasons of a Man's Life (http://refer.ly/a4hO) is the work of a few researchers. They were frustrated that most work in psychology studied childhood development in depth, but little research was done into development during your 30s, 40s, 50s and 60s. The research is focused entirely on guys (sorry ladies). Not surprisingly, he was able to find several phases most men go through. Several friends have found the book really helpful when they're reflecting on life.
The Up Series (http://refer.ly/a4hN) is a set of films, each shot every 7 years that chronicles the real lives of a dozen people from England. While it has a bit of reality TV "drama", most all of it is the real unvarnished changes that people go through as they age, including their regrets and accomplishments. It's a remarkable watch, given that you get to see people age from 7 to 56. Just as an example, I feel it prepared me ahead of time to deal with the death of my mother, and savor the time that I have with my dad who's still alive. Ultimately, we all have to face up to a lot of the same things, and it's comforting to have a bit of a map.